Chestertown: 8 hotels found

Searching for hotels in Chestertown? Compare room rates and reviews to find your ideal stay.
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Hotels with: Pets allowed

Hotels with: Pets allowed

2 hotels
Hotels with: Parking

Hotels with: Parking

2 hotels
Hotels with: Wi-Fi

Hotels with: Wi-Fi

2 hotels
Hotels with: Gym

Hotels with: Gym

1 hotel
Hotels with: Swimming Pools

Hotels with: Swimming Pools

1 hotel

Hotels You May Like in Chestertown

Check out our selection of great hotels in Chestertown.

5 star

Red Roof Inn & Suites Chestertown
3.7/599 Reviews

Red Roof Inn & Suites Chestertown

Chestertown|1.03km from city centre
My stay was supposed to be at comfort inn but it was at the red roof inn. I called in and was compensated for the mix up. The situation was resolved quickly and professionally. Thanks to the guy in customer service we appreciated his promptness and great service.
Driftwood Inn
2.7/520 Reviews

Driftwood Inn

Chestertown|0.45km from city centre
Located in Chestertown, Driftwood Inn is within a 15-minute drive of Washington College and Rolphs Wharf Marina. This motel is 12.1 mi (19.4 km) from Betterton Beach and 13.5 mi (21.7 km) from Rock Hall Harbor.This motel has 1 floor in 2 buildings and offers designated smoking areas.Featured amenities include express check-in, express check-out, and a 24-hour front desk. Free self parking is available onsite.Make yourself at home in one of the 28 guestrooms featuring refrigerators and microwaves. Complimentary wireless internet access keeps you connected, and satellite programming is available for your entertainment. Private bathrooms with bathtubs or showers feature complimentary toiletries and hair dryers. Conveniences include desks and coffee/tea makers, as well as phones with free local calls.

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Business travel

Red Roof Inn & Suites Chestertown
3.7/599 Reviews

Red Roof Inn & Suites Chestertown

Chestertown|1.03km from city centre
My stay was supposed to be at comfort inn but it was at the red roof inn. I called in and was compensated for the mix up. The situation was resolved quickly and professionally. Thanks to the guy in customer service we appreciated his promptness and great service.
Driftwood Inn
2.7/520 Reviews

Driftwood Inn

Chestertown|0.45km from city centre
Located in Chestertown, Driftwood Inn is within a 15-minute drive of Washington College and Rolphs Wharf Marina. This motel is 12.1 mi (19.4 km) from Betterton Beach and 13.5 mi (21.7 km) from Rock Hall Harbor.This motel has 1 floor in 2 buildings and offers designated smoking areas.Featured amenities include express check-in, express check-out, and a 24-hour front desk. Free self parking is available onsite.Make yourself at home in one of the 28 guestrooms featuring refrigerators and microwaves. Complimentary wireless internet access keeps you connected, and satellite programming is available for your entertainment. Private bathrooms with bathtubs or showers feature complimentary toiletries and hair dryers. Conveniences include desks and coffee/tea makers, as well as phones with free local calls.
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

Chestertown|0.97km from city centre
Be at your best when you stay at the Comfort Inn and Suites Chestertown hotel in Chestertown right in the heart of the great outdoors in eastern Maryland. Amenities include free WiFi, free parking, free hot breakfast, a fitness center, business center, meeting space, a seasonal outdoor pool and more. Every room comes with a flat-screen TV, microwave, refrigerator, recharge stations and more. We also offer larger suites with a sleeper sofa and wet bar. Find us off MD-291 about 90 minutes from Philadelphia, Washington DC and Baltimore. We are also down the street from Washington College and just minutes from the Chester River. Our hotel in Chestertown offers the perfect home base for exploring the area. Plus, you can earn rewards, including free nights and gift cards, with our Choice Privileges Rewards program. Pets allowed 20.00 per stay. Max 40 lbs, 2 pets per room.

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Breakfast

Red Roof Inn & Suites Chestertown
3.7/599 Reviews

Red Roof Inn & Suites Chestertown

Chestertown|1.03km from city centre
My stay was supposed to be at comfort inn but it was at the red roof inn. I called in and was compensated for the mix up. The situation was resolved quickly and professionally. Thanks to the guy in customer service we appreciated his promptness and great service.
Driftwood Inn
2.7/520 Reviews

Driftwood Inn

Chestertown|0.45km from city centre
Located in Chestertown, Driftwood Inn is within a 15-minute drive of Washington College and Rolphs Wharf Marina. This motel is 12.1 mi (19.4 km) from Betterton Beach and 13.5 mi (21.7 km) from Rock Hall Harbor.This motel has 1 floor in 2 buildings and offers designated smoking areas.Featured amenities include express check-in, express check-out, and a 24-hour front desk. Free self parking is available onsite.Make yourself at home in one of the 28 guestrooms featuring refrigerators and microwaves. Complimentary wireless internet access keeps you connected, and satellite programming is available for your entertainment. Private bathrooms with bathtubs or showers feature complimentary toiletries and hair dryers. Conveniences include desks and coffee/tea makers, as well as phones with free local calls.
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

Chestertown|0.97km from city centre
Be at your best when you stay at the Comfort Inn and Suites Chestertown hotel in Chestertown right in the heart of the great outdoors in eastern Maryland. Amenities include free WiFi, free parking, free hot breakfast, a fitness center, business center, meeting space, a seasonal outdoor pool and more. Every room comes with a flat-screen TV, microwave, refrigerator, recharge stations and more. We also offer larger suites with a sleeper sofa and wet bar. Find us off MD-291 about 90 minutes from Philadelphia, Washington DC and Baltimore. We are also down the street from Washington College and just minutes from the Chester River. Our hotel in Chestertown offers the perfect home base for exploring the area. Plus, you can earn rewards, including free nights and gift cards, with our Choice Privileges Rewards program. Pets allowed 20.00 per stay. Max 40 lbs, 2 pets per room.

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Family friendly

Red Roof Inn & Suites Chestertown
3.7/599 Reviews

Red Roof Inn & Suites Chestertown

Chestertown|1.03km from city centre
My stay was supposed to be at comfort inn but it was at the red roof inn. I called in and was compensated for the mix up. The situation was resolved quickly and professionally. Thanks to the guy in customer service we appreciated his promptness and great service.
Driftwood Inn
2.7/520 Reviews

Driftwood Inn

Chestertown|0.45km from city centre
Located in Chestertown, Driftwood Inn is within a 15-minute drive of Washington College and Rolphs Wharf Marina. This motel is 12.1 mi (19.4 km) from Betterton Beach and 13.5 mi (21.7 km) from Rock Hall Harbor.This motel has 1 floor in 2 buildings and offers designated smoking areas.Featured amenities include express check-in, express check-out, and a 24-hour front desk. Free self parking is available onsite.Make yourself at home in one of the 28 guestrooms featuring refrigerators and microwaves. Complimentary wireless internet access keeps you connected, and satellite programming is available for your entertainment. Private bathrooms with bathtubs or showers feature complimentary toiletries and hair dryers. Conveniences include desks and coffee/tea makers, as well as phones with free local calls.
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

Chestertown|0.97km from city centre
Be at your best when you stay at the Comfort Inn and Suites Chestertown hotel in Chestertown right in the heart of the great outdoors in eastern Maryland. Amenities include free WiFi, free parking, free hot breakfast, a fitness center, business center, meeting space, a seasonal outdoor pool and more. Every room comes with a flat-screen TV, microwave, refrigerator, recharge stations and more. We also offer larger suites with a sleeper sofa and wet bar. Find us off MD-291 about 90 minutes from Philadelphia, Washington DC and Baltimore. We are also down the street from Washington College and just minutes from the Chester River. Our hotel in Chestertown offers the perfect home base for exploring the area. Plus, you can earn rewards, including free nights and gift cards, with our Choice Privileges Rewards program. Pets allowed 20.00 per stay. Max 40 lbs, 2 pets per room.

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Hotels Near Famous Attractions in Chestertown

Check out these hotels located near popular sights in Chestertown

Washington College

Driftwood Inn
2.7/520 Reviews

Driftwood Inn

Chestertown|0.53km from Washington College
Located in Chestertown, Driftwood Inn is within a 15-minute drive of Washington College and Rolphs Wharf Marina. This motel is 12.1 mi (19.4 km) from Betterton Beach and 13.5 mi (21.7 km) from Rock Hall Harbor.This motel has 1 floor in 2 buildings and offers designated smoking areas.Featured amenities include express check-in, express check-out, and a 24-hour front desk. Free self parking is available onsite.Make yourself at home in one of the 28 guestrooms featuring refrigerators and microwaves. Complimentary wireless internet access keeps you connected, and satellite programming is available for your entertainment. Private bathrooms with bathtubs or showers feature complimentary toiletries and hair dryers. Conveniences include desks and coffee/tea makers, as well as phones with free local calls.
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

Chestertown|1.04km from Washington College
Be at your best when you stay at the Comfort Inn and Suites Chestertown hotel in Chestertown right in the heart of the great outdoors in eastern Maryland. Amenities include free WiFi, free parking, free hot breakfast, a fitness center, business center, meeting space, a seasonal outdoor pool and more. Every room comes with a flat-screen TV, microwave, refrigerator, recharge stations and more. We also offer larger suites with a sleeper sofa and wet bar. Find us off MD-291 about 90 minutes from Philadelphia, Washington DC and Baltimore. We are also down the street from Washington College and just minutes from the Chester River. Our hotel in Chestertown offers the perfect home base for exploring the area. Plus, you can earn rewards, including free nights and gift cards, with our Choice Privileges Rewards program. Pets allowed 20.00 per stay. Max 40 lbs, 2 pets per room.
Red Roof Inn & Suites Chestertown
3.7/599 Reviews

Red Roof Inn & Suites Chestertown

Chestertown|1.1km from Washington College
My stay was supposed to be at comfort inn but it was at the red roof inn. I called in and was compensated for the mix up. The situation was resolved quickly and professionally. Thanks to the guy in customer service we appreciated his promptness and great service.
The Lodge at Great Oak Landing
3.8/51 Reviews

The Lodge at Great Oak Landing

Kent County
With a stay at The Lodge at Great Oak Landing in Chestertown, you'll be 8.8 mi (14.2 km) from Washington College and 9.6 mi (15.5 km) from Garfield Center for the Arts at the Prince Theater. This beach lodge is 12.5 mi (20.1 km) from The Mainstay and 16.9 mi (27.2 km) from Church Hill Theatre.Practice your swing on the golf course or soak up the sunshine on the private beach. This lodge also features complimentary wireless Internet access, gift shops/newsstands, and a picnic area.At The Lodge at Great Oak Landing, enjoy a satisfying meal at the restaurant. Relax with a refreshing drink from the poolside bar or one of the 3 bars/lounges.Featured amenities include laundry facilities, ATM/banking services, and coffee/tea in a common area. Free self parking is available onsite.Stay in one of 29 guestrooms featuring flat-screen televisions. Complimentary wireless Internet access keeps you connected, and cable programming is available for your entertainment. Conveniences include phones, and housekeeping is provided on request.
Mariner's Motel
4.6/539 Reviews

Mariner's Motel

Rock Hall
Located in Rock Hall, Mariners Motel is near the bay, a 3-minute walk from Rock Hall Harbor and 13 minutes by foot from Ferry Park. This motel is 0.7 mi (1.1 km) from The Mainstay and 6.5 mi (10.5 km) from Eastern Neck National Wildlife Refuge.Enjoy recreation amenities such as an outdoor pool or take in the view from a garden. Additional amenities at this motel include complimentary wireless internet access, a picnic area, and charcoal grills.The front desk is staffed during limited hours. Free self parking is available onsite.Make yourself at home in one of the 12 guestrooms featuring refrigerators. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Bathrooms have shower/tub combinations and hair dryers. Conveniences include coffee/tea makers and ceiling fans, and housekeeping is provided daily.
Inn at Huntingfield Creek
4.9/549 Reviews

Inn at Huntingfield Creek

Rock Hall
Located in Rock Hall, Inn at Huntingfield Creek is on the waterfront, within a 5-minute drive of The Mainstay and Rock Hall Harbor. This spa bed & breakfast is 2.6 mi (4.1 km) from Waterman’s Museum and 3.3 mi (5.4 km) from Ferry Park.Pamper yourself with a visit to the spa, which offers massages. You can take advantage of recreational amenities such as an outdoor pool and bicycles to rent. Additional features at this bed & breakfast include complimentary wireless internet access, tour/ticket assistance, and a picnic area.Free self parking is available onsite.Make yourself at home in one of the 12 air-conditioned rooms featuring fireplaces and flat-screen televisions. Your memory foam bed comes with Egyptian cotton sheets. Rooms have private balconies or patios. Kitchens are outfitted with full-sized refrigerators/freezers, ovens, and stovetops. Complimentary wireless internet access is available to keep you connected. Private bathrooms have jetted bathtubs and complimentary toiletries.

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Emmanuel Episcopal Church

Driftwood Inn
2.7/520 Reviews

Driftwood Inn

Chestertown|1.52km from Emmanuel Episcopal Church
Located in Chestertown, Driftwood Inn is within a 15-minute drive of Washington College and Rolphs Wharf Marina. This motel is 12.1 mi (19.4 km) from Betterton Beach and 13.5 mi (21.7 km) from Rock Hall Harbor.This motel has 1 floor in 2 buildings and offers designated smoking areas.Featured amenities include express check-in, express check-out, and a 24-hour front desk. Free self parking is available onsite.Make yourself at home in one of the 28 guestrooms featuring refrigerators and microwaves. Complimentary wireless internet access keeps you connected, and satellite programming is available for your entertainment. Private bathrooms with bathtubs or showers feature complimentary toiletries and hair dryers. Conveniences include desks and coffee/tea makers, as well as phones with free local calls.
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

Chestertown|2.06km from Emmanuel Episcopal Church
Be at your best when you stay at the Comfort Inn and Suites Chestertown hotel in Chestertown right in the heart of the great outdoors in eastern Maryland. Amenities include free WiFi, free parking, free hot breakfast, a fitness center, business center, meeting space, a seasonal outdoor pool and more. Every room comes with a flat-screen TV, microwave, refrigerator, recharge stations and more. We also offer larger suites with a sleeper sofa and wet bar. Find us off MD-291 about 90 minutes from Philadelphia, Washington DC and Baltimore. We are also down the street from Washington College and just minutes from the Chester River. Our hotel in Chestertown offers the perfect home base for exploring the area. Plus, you can earn rewards, including free nights and gift cards, with our Choice Privileges Rewards program. Pets allowed 20.00 per stay. Max 40 lbs, 2 pets per room.
Red Roof Inn & Suites Chestertown
3.7/599 Reviews

Red Roof Inn & Suites Chestertown

Chestertown|2.11km from Emmanuel Episcopal Church
My stay was supposed to be at comfort inn but it was at the red roof inn. I called in and was compensated for the mix up. The situation was resolved quickly and professionally. Thanks to the guy in customer service we appreciated his promptness and great service.
The Lodge at Great Oak Landing
3.8/51 Reviews

The Lodge at Great Oak Landing

Kent County
With a stay at The Lodge at Great Oak Landing in Chestertown, you'll be 8.8 mi (14.2 km) from Washington College and 9.6 mi (15.5 km) from Garfield Center for the Arts at the Prince Theater. This beach lodge is 12.5 mi (20.1 km) from The Mainstay and 16.9 mi (27.2 km) from Church Hill Theatre.Practice your swing on the golf course or soak up the sunshine on the private beach. This lodge also features complimentary wireless Internet access, gift shops/newsstands, and a picnic area.At The Lodge at Great Oak Landing, enjoy a satisfying meal at the restaurant. Relax with a refreshing drink from the poolside bar or one of the 3 bars/lounges.Featured amenities include laundry facilities, ATM/banking services, and coffee/tea in a common area. Free self parking is available onsite.Stay in one of 29 guestrooms featuring flat-screen televisions. Complimentary wireless Internet access keeps you connected, and cable programming is available for your entertainment. Conveniences include phones, and housekeeping is provided on request.
Mariner's Motel
4.6/539 Reviews

Mariner's Motel

Rock Hall
Located in Rock Hall, Mariners Motel is near the bay, a 3-minute walk from Rock Hall Harbor and 13 minutes by foot from Ferry Park. This motel is 0.7 mi (1.1 km) from The Mainstay and 6.5 mi (10.5 km) from Eastern Neck National Wildlife Refuge.Enjoy recreation amenities such as an outdoor pool or take in the view from a garden. Additional amenities at this motel include complimentary wireless internet access, a picnic area, and charcoal grills.The front desk is staffed during limited hours. Free self parking is available onsite.Make yourself at home in one of the 12 guestrooms featuring refrigerators. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Bathrooms have shower/tub combinations and hair dryers. Conveniences include coffee/tea makers and ceiling fans, and housekeeping is provided daily.
Inn at Huntingfield Creek
4.9/549 Reviews

Inn at Huntingfield Creek

Rock Hall
Located in Rock Hall, Inn at Huntingfield Creek is on the waterfront, within a 5-minute drive of The Mainstay and Rock Hall Harbor. This spa bed & breakfast is 2.6 mi (4.1 km) from Waterman’s Museum and 3.3 mi (5.4 km) from Ferry Park.Pamper yourself with a visit to the spa, which offers massages. You can take advantage of recreational amenities such as an outdoor pool and bicycles to rent. Additional features at this bed & breakfast include complimentary wireless internet access, tour/ticket assistance, and a picnic area.Free self parking is available onsite.Make yourself at home in one of the 12 air-conditioned rooms featuring fireplaces and flat-screen televisions. Your memory foam bed comes with Egyptian cotton sheets. Rooms have private balconies or patios. Kitchens are outfitted with full-sized refrigerators/freezers, ovens, and stovetops. Complimentary wireless internet access is available to keep you connected. Private bathrooms have jetted bathtubs and complimentary toiletries.

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Twigs & Teacups

Driftwood Inn
2.7/520 Reviews

Driftwood Inn

Chestertown|1.61km from Twigs & Teacups
Located in Chestertown, Driftwood Inn is within a 15-minute drive of Washington College and Rolphs Wharf Marina. This motel is 12.1 mi (19.4 km) from Betterton Beach and 13.5 mi (21.7 km) from Rock Hall Harbor.This motel has 1 floor in 2 buildings and offers designated smoking areas.Featured amenities include express check-in, express check-out, and a 24-hour front desk. Free self parking is available onsite.Make yourself at home in one of the 28 guestrooms featuring refrigerators and microwaves. Complimentary wireless internet access keeps you connected, and satellite programming is available for your entertainment. Private bathrooms with bathtubs or showers feature complimentary toiletries and hair dryers. Conveniences include desks and coffee/tea makers, as well as phones with free local calls.
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

Chestertown|2.14km from Twigs & Teacups
Be at your best when you stay at the Comfort Inn and Suites Chestertown hotel in Chestertown right in the heart of the great outdoors in eastern Maryland. Amenities include free WiFi, free parking, free hot breakfast, a fitness center, business center, meeting space, a seasonal outdoor pool and more. Every room comes with a flat-screen TV, microwave, refrigerator, recharge stations and more. We also offer larger suites with a sleeper sofa and wet bar. Find us off MD-291 about 90 minutes from Philadelphia, Washington DC and Baltimore. We are also down the street from Washington College and just minutes from the Chester River. Our hotel in Chestertown offers the perfect home base for exploring the area. Plus, you can earn rewards, including free nights and gift cards, with our Choice Privileges Rewards program. Pets allowed 20.00 per stay. Max 40 lbs, 2 pets per room.
Red Roof Inn & Suites Chestertown
3.7/599 Reviews

Red Roof Inn & Suites Chestertown

Chestertown|2.2km from Twigs & Teacups
My stay was supposed to be at comfort inn but it was at the red roof inn. I called in and was compensated for the mix up. The situation was resolved quickly and professionally. Thanks to the guy in customer service we appreciated his promptness and great service.
The Lodge at Great Oak Landing
3.8/51 Reviews

The Lodge at Great Oak Landing

Kent County
With a stay at The Lodge at Great Oak Landing in Chestertown, you'll be 8.8 mi (14.2 km) from Washington College and 9.6 mi (15.5 km) from Garfield Center for the Arts at the Prince Theater. This beach lodge is 12.5 mi (20.1 km) from The Mainstay and 16.9 mi (27.2 km) from Church Hill Theatre.Practice your swing on the golf course or soak up the sunshine on the private beach. This lodge also features complimentary wireless Internet access, gift shops/newsstands, and a picnic area.At The Lodge at Great Oak Landing, enjoy a satisfying meal at the restaurant. Relax with a refreshing drink from the poolside bar or one of the 3 bars/lounges.Featured amenities include laundry facilities, ATM/banking services, and coffee/tea in a common area. Free self parking is available onsite.Stay in one of 29 guestrooms featuring flat-screen televisions. Complimentary wireless Internet access keeps you connected, and cable programming is available for your entertainment. Conveniences include phones, and housekeeping is provided on request.
Mariner's Motel
4.6/539 Reviews

Mariner's Motel

Rock Hall
Located in Rock Hall, Mariners Motel is near the bay, a 3-minute walk from Rock Hall Harbor and 13 minutes by foot from Ferry Park. This motel is 0.7 mi (1.1 km) from The Mainstay and 6.5 mi (10.5 km) from Eastern Neck National Wildlife Refuge.Enjoy recreation amenities such as an outdoor pool or take in the view from a garden. Additional amenities at this motel include complimentary wireless internet access, a picnic area, and charcoal grills.The front desk is staffed during limited hours. Free self parking is available onsite.Make yourself at home in one of the 12 guestrooms featuring refrigerators. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Bathrooms have shower/tub combinations and hair dryers. Conveniences include coffee/tea makers and ceiling fans, and housekeeping is provided daily.
Inn at Huntingfield Creek
4.9/549 Reviews

Inn at Huntingfield Creek

Rock Hall
Located in Rock Hall, Inn at Huntingfield Creek is on the waterfront, within a 5-minute drive of The Mainstay and Rock Hall Harbor. This spa bed & breakfast is 2.6 mi (4.1 km) from Waterman’s Museum and 3.3 mi (5.4 km) from Ferry Park.Pamper yourself with a visit to the spa, which offers massages. You can take advantage of recreational amenities such as an outdoor pool and bicycles to rent. Additional features at this bed & breakfast include complimentary wireless internet access, tour/ticket assistance, and a picnic area.Free self parking is available onsite.Make yourself at home in one of the 12 air-conditioned rooms featuring fireplaces and flat-screen televisions. Your memory foam bed comes with Egyptian cotton sheets. Rooms have private balconies or patios. Kitchens are outfitted with full-sized refrigerators/freezers, ovens, and stovetops. Complimentary wireless internet access is available to keep you connected. Private bathrooms have jetted bathtubs and complimentary toiletries.

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Garfield Center for the Arts at the Prince Theatre

Driftwood Inn
2.7/520 Reviews

Driftwood Inn

Chestertown|1.62km from Garfield Center for the Arts at the Prince Theatre
Located in Chestertown, Driftwood Inn is within a 15-minute drive of Washington College and Rolphs Wharf Marina. This motel is 12.1 mi (19.4 km) from Betterton Beach and 13.5 mi (21.7 km) from Rock Hall Harbor.This motel has 1 floor in 2 buildings and offers designated smoking areas.Featured amenities include express check-in, express check-out, and a 24-hour front desk. Free self parking is available onsite.Make yourself at home in one of the 28 guestrooms featuring refrigerators and microwaves. Complimentary wireless internet access keeps you connected, and satellite programming is available for your entertainment. Private bathrooms with bathtubs or showers feature complimentary toiletries and hair dryers. Conveniences include desks and coffee/tea makers, as well as phones with free local calls.
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

Chestertown|2.15km from Garfield Center for the Arts at the Prince Theatre
Be at your best when you stay at the Comfort Inn and Suites Chestertown hotel in Chestertown right in the heart of the great outdoors in eastern Maryland. Amenities include free WiFi, free parking, free hot breakfast, a fitness center, business center, meeting space, a seasonal outdoor pool and more. Every room comes with a flat-screen TV, microwave, refrigerator, recharge stations and more. We also offer larger suites with a sleeper sofa and wet bar. Find us off MD-291 about 90 minutes from Philadelphia, Washington DC and Baltimore. We are also down the street from Washington College and just minutes from the Chester River. Our hotel in Chestertown offers the perfect home base for exploring the area. Plus, you can earn rewards, including free nights and gift cards, with our Choice Privileges Rewards program. Pets allowed 20.00 per stay. Max 40 lbs, 2 pets per room.
Red Roof Inn & Suites Chestertown
3.7/599 Reviews

Red Roof Inn & Suites Chestertown

Chestertown|2.2km from Garfield Center for the Arts at the Prince Theatre
My stay was supposed to be at comfort inn but it was at the red roof inn. I called in and was compensated for the mix up. The situation was resolved quickly and professionally. Thanks to the guy in customer service we appreciated his promptness and great service.
The Lodge at Great Oak Landing
3.8/51 Reviews

The Lodge at Great Oak Landing

Kent County
With a stay at The Lodge at Great Oak Landing in Chestertown, you'll be 8.8 mi (14.2 km) from Washington College and 9.6 mi (15.5 km) from Garfield Center for the Arts at the Prince Theater. This beach lodge is 12.5 mi (20.1 km) from The Mainstay and 16.9 mi (27.2 km) from Church Hill Theatre.Practice your swing on the golf course or soak up the sunshine on the private beach. This lodge also features complimentary wireless Internet access, gift shops/newsstands, and a picnic area.At The Lodge at Great Oak Landing, enjoy a satisfying meal at the restaurant. Relax with a refreshing drink from the poolside bar or one of the 3 bars/lounges.Featured amenities include laundry facilities, ATM/banking services, and coffee/tea in a common area. Free self parking is available onsite.Stay in one of 29 guestrooms featuring flat-screen televisions. Complimentary wireless Internet access keeps you connected, and cable programming is available for your entertainment. Conveniences include phones, and housekeeping is provided on request.
Mariner's Motel
4.6/539 Reviews

Mariner's Motel

Rock Hall
Located in Rock Hall, Mariners Motel is near the bay, a 3-minute walk from Rock Hall Harbor and 13 minutes by foot from Ferry Park. This motel is 0.7 mi (1.1 km) from The Mainstay and 6.5 mi (10.5 km) from Eastern Neck National Wildlife Refuge.Enjoy recreation amenities such as an outdoor pool or take in the view from a garden. Additional amenities at this motel include complimentary wireless internet access, a picnic area, and charcoal grills.The front desk is staffed during limited hours. Free self parking is available onsite.Make yourself at home in one of the 12 guestrooms featuring refrigerators. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Bathrooms have shower/tub combinations and hair dryers. Conveniences include coffee/tea makers and ceiling fans, and housekeeping is provided daily.
Inn at Huntingfield Creek
4.9/549 Reviews

Inn at Huntingfield Creek

Rock Hall
Located in Rock Hall, Inn at Huntingfield Creek is on the waterfront, within a 5-minute drive of The Mainstay and Rock Hall Harbor. This spa bed & breakfast is 2.6 mi (4.1 km) from Waterman’s Museum and 3.3 mi (5.4 km) from Ferry Park.Pamper yourself with a visit to the spa, which offers massages. You can take advantage of recreational amenities such as an outdoor pool and bicycles to rent. Additional features at this bed & breakfast include complimentary wireless internet access, tour/ticket assistance, and a picnic area.Free self parking is available onsite.Make yourself at home in one of the 12 air-conditioned rooms featuring fireplaces and flat-screen televisions. Your memory foam bed comes with Egyptian cotton sheets. Rooms have private balconies or patios. Kitchens are outfitted with full-sized refrigerators/freezers, ovens, and stovetops. Complimentary wireless internet access is available to keep you connected. Private bathrooms have jetted bathtubs and complimentary toiletries.

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Top rated hotels in Chestertown

Looking for hotels in Chestertown? Get inspired by reviews from real travellers.
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

3.7/599 Reviews
My stay was supposed to be at comfort inn but it was at the red roof inn. I called in and was compensated for the mix up. The situation was resolved quickly and professionally. Thanks to the guy in customer service we appreciated his promptness and great service.

Frequently Asked Questions

  • What are the popular hotels in Chestertown?

    Chestertown has many popular hotels. Whether you're traveling for business or going on a vacation, Red Roof Inn & Suites Chestertown and Driftwood Inn are preferred hotels.

  • How much is the average rate for hotels in Chestertown?

    For hotels in Chestertown, the average price on weekdays is CAD 141, the average price on weekends (Friday–Saturday) is CAD 184.

  • Which hotels in Chestertown provide fitness facilities?

    Red Roof Inn & Suites Chestertown provides fitness facilities. Satisfy your fitness needs even while traveling!

  • Which hotels in Chestertown have swimming pools?

    Red Roof Inn & Suites Chestertown is a hotel with swimming pools. Stay at any of these hotels to enjoy a swimming pool!

  • Which hotels in Chestertown provide free Wi-Fi?

    Whether you're traveling on business or for vacation, Internet connection is an essential condition for travel. Red Roof Inn & Suites Chestertown and Driftwood Inn are popular hotels with free Wi-Fi.

  • What hotel promotions are there in Chestertown?

    Trip.com provides various promotions and discounts for users all year round. You can check the promotions page to see what promotions are available on Trip.com.

Local Travel Info

Highest PriceCAD 424
Lowest PriceCAD 96
Number of Reviews 294
Number of hotels14
Average Price(Weekday Night)CAD 141
Average Price(Weekend Night)CAD 184