Best Hotels in Chestertown

Explore Chestertown hotels and choose from 24 properties near landmarks, luxury hotels, and top boutiques for the best shopping and dining.

The Fern Lodge
9.7 (24 reviews)

The Fern Lodge ★★★★

📍 46 Fiddlehead Bay Rd, Chestertown

"A beautiful B&B on Friends Lake with extensive common facilities. Our spacious “Pine” accommodation was truly exceptional, featuring a large stone fireplace and private covered deck with views of the lake. The meticulously landscaped grounds lead down to a pretty boathouse and dock on quiet cove. Breakfast and service were excellent. This is a great place to unwind for a couple days."

Pine Tree Motel & Cabins
9.1 (39 reviews)

Pine Tree Motel & Cabins ★★

📍 5537 State Route 8, Chestertown

"We truly enjoyed our short stay at the Pine Tree Motel Cabins! It was extraordinarily hot outdoors this summer July 4th holiday, but along with a cool shower, our small cabin’s air conditioning made it very comfortable after a long day’s drive there from NYC. The cabins sit independently for privacy with a space for your vehicle. Our cabin was clean, stocked with toiletries and we were able to connect to the WiFi with ease and our television was cable ready. On the grounds, we experienced very peaceful mornings, people drinking their coffee on the porch. We would return afternoons to see some folks grilling their food while small children played outside. The nights were very calm quiet and the property was beautifully lit for added safety. The hosts here are the owners of the property, and do seem to give individual attention to their guests in our experience. They introduced themselves and are genuinely sweet and friendly people. They gave us suggestions on where to eat and directions to different locations. We enjoyed getting to know them a bit personally which you don’t get at the big chain style hotels. Angela met and pet our dog and wanted him to be as comfortable there as we were! We would certainly stay there again as this was our first trip to the Adirondacks region. We thank them for a lovely stay! - Amanda and Jorge"

Rustic Adirondacks Home w/ Hot Tub & Lake Access!
9.8 (3 reviews)

Rustic Adirondacks Home w/ Hot Tub & Lake Access! ★★★

📍 7133 U.S. 9, Chestertown

All-season Family Retreat w/ Dock on Loon Lake!
10 (7 reviews)

All-season Family Retreat w/ Dock on Loon Lake! ★★★★

📍 13 Marina Rd, Chestertown

Adirondack Retreat w/ Heated Pool & Scenic Views!
9.8 (1 reviews)

Adirondack Retreat w/ Heated Pool & Scenic Views! ★★★

📍 108 Igerna Rd, Chestertown

Camp RiverWood on the Hudson River
9.8 (12 reviews)

Camp RiverWood on the Hudson River ★★★

📍 Chestertown

Elizabeth. 15 Minutes to Lake George.Seasonal Heated Pool.
8.2 (61 reviews)

Elizabeth. 15 Minutes to Lake George.Seasonal Heated Pool. ★★★★

📍 Chestertown

Private Dock & Beach! Lakefront, Fire-pit, Boats
10 (4 reviews)

Private Dock & Beach! Lakefront, Fire-pit, Boats ★★★

📍 206 Hill Park Rd, Chestertown

Beautiful cottage on quiet country road walking distance to charming North Creek
9.8 (56 reviews)

Beautiful cottage on quiet country road walking distance to charming North Creek ★★★

📍 Chestertown

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Guest Reviews on Chestertown Hotels

10.0
Excellent Community Rating
Real & verified guest reviews from around the world
G

Guest User

Other
The Fern Lodge ★★★★
"Wonderful spot, great amenities, quietly luxurious rooms, with all the amenities while still being cozy and charming. There's so much to do and explore, indoors and out. We loved playing pool, the hot tub, the hiking trails. The lake is quiet and peaceful, and you are close enough to explore Lake George if you wish -- without being stuck in the crowds. We especially enjoyed the off season, but the lake is private, so it's likely peaceful even in July. We can't wait to go back!"
★★★★★
2026-05-05
G

Guest User

Other
Pine Tree Motel & Cabins ★★
"I chose this place to stay for an excursion into the Adirondacks based on the charming photos on Google maps and the affordability. I'm please to report that Pine Tree Motel and Cabins is a true hidden gem. Cozy, rustic, remote, and surrounded by the almost overwhelming beauty of upstate New York. Norleen is an amazing owner and caretaker and jumped at every chance to make our stay a dream. Being amateur travelers, we over packed for the size of the cabin we stayed in, but that was our fault and otherwise the cabin was more than spacious and well-furnished enough for two lovebirds. 10/10, fully intend to stay here again someday soon. Thank you Norleen and Bert!"
★★★★★
2025-07-03

Chestertown Travel Information

⚡

Power Plug & Voltage

120V/Type A/B

💵

Exchange Rate

1 CAD ≈ 0.71 USD

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Local Payment

Cards/ApplePay/Cash

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Connectivity

Verizon/AT&T/T-Mobile

More Information About Chestertown Hotels

Key Info

Details

Number of reviews

306

Total properties

24

Weekday Avg. Price

CAD 445

Weekend Avg. Price

CAD 455

Trending hotel

The Fern Lodge

FAQs About Hotels in Chestertown

  • What are the most popular hotels in Chestertown?

    There are many popular options for hotels in Chestertown. Whether you're traveling for business or a vacation, The Fern Lodge (from CAD 585) and Pine Tree Motel & Cabins (from CAD 272) are popular choices.

  • What is the average price for hotels in Chestertown?

    The average price for hotels in Chestertown is CAD 445 for weekdays, and CAD 455 for weekends (Friday–Saturday).

  • What are popular hotels with high-quality breakfasts in Chestertown?

    The Fern Lodge (from CAD 585) is top hotel with high-quality breakfast. Start your wonderful journey with tasty breakfast!

  • What are available deals for hotels in Chestertown?

    There are multiple promotions and discounts all year round for Trip.com users . Please check the promotions page to see what promotions are available now on Trip.com.

  • Which hotels with fitness facilities in Chestertown are popular?

    The Fern Lodge (from CAD 585) is a popular hotel with a fitness center. Keep your fitness plan during traveling from Trip.com!

  • Which popular hotels in Chestertown offer free Wi-Fi ?

    Whether you're traveling on business or for vacation, internet connection is an essential facility. The Fern Lodge (from CAD 585) and Pine Tree Motel & Cabins (from CAD 272) are popular hotels with free Wi-Fi.

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