Best Hotels in Chestertown

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

Pine Tree Motel & Cabins
9.1 (35 reviews)

Pine Tree Motel & Cabins ★★

📍 5537 State Route 8, Chestertown

"A cozy and convenient dog friendly stay with access to hiking and walking trails, white water rafting on the Hudson River, Brant and Loon Lakes, and Lake George. Chestertown is a sweet little gem and the Pine Tree Motel has both rooms and cabins far enough away from the road for quiet, a serene backyard, and very comfy beds! A very comfortable home base for solo travel with a pooch."

The Fern Lodge
9.7 (23 reviews)

The Fern Lodge ★★★★

📍 46 Fiddlehead Bay Rd, Chestertown

"I made a reservation for two nights at the Fern Lodge in July 2024. Sadly I became extremely ill two days before our reservation. I’m not sure who I talked to, but the person was rude and not even the least bit understanding. The cancellation policy was two weeks; obviously I didn’t cancel at that time because I wasn’t sick and had every intention of going and was really looking forward to it. So, not only was there ZERO compassion from the manager, but THEY wouldn’t even let me ‘give’’ the reservation to my family or friends in the area. And my family who has a cabin on Friend’s lake, has been an acquaintance of the owners for years. The reservation was cancelled and they refused to allow any other options. It was like flushing $1000+ down the loo. I cannot recommend this place, and we’ve made sure that our local friends know how horribly I was treated, all while I was soooo sick. The least they could have done is allowed someone else to stay in our place, but the woman I talked to refused. She cancelled the reservation and that was that. My family have been telling everyone how poorly I was treated, and locals were shocked that the owners did this. Greed is greed, but why on earth wouldn’t they have let someone else stay in our place? I mean, it was paid for in full, so why would they care? Avoid, avoid, avoid. The experience of being treated so poorly was demoralizing. Stay at Friend's Inn. The management at Fern Lake sucks and we will tell everyone we can."

Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing
10 (27 reviews)

Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing ★★★

📍 Chestertown

Great Adirondacks  retreat with five bedroomsHot tub,pool table.large open space
8.8 (14 reviews)

Great Adirondacks retreat with five bedroomsHot tub,pool table.large open space ★★★

📍 Chestertown

This is a beautiful house that sits facing Loon Lake! Amazing views and dock!!!
9.8 (5 reviews)

This is a beautiful house that sits facing Loon Lake! Amazing views and dock!!! ★★★

📍 Chestertown

GORGEOUS FAMILY FRIENDLY VICTORIAN WITH ALL NATURAL CEDAR HOT TUB NEAR GORE MT
10 (19 reviews)

GORGEOUS FAMILY FRIENDLY VICTORIAN WITH ALL NATURAL CEDAR HOT TUB NEAR GORE MT ★★★

📍 Chestertown

Beautiful cottage on quiet country road walking distance to charming North Creek
9.8 (33 reviews)

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

📍 Chestertown

3 bedroom cabin in Chestertown with hot tub, fireplace, fire pit, wifi, and more
10 (12 reviews)

3 bedroom cabin in Chestertown with hot tub, fireplace, fire pit, wifi, and more ★★★★

📍 Chestertown

Vintage Adk Cabin- Great Deal, Perfect Location, Book Your Gore Mtn. Trip Today!
9.4 (13 reviews)

Vintage Adk Cabin- Great Deal, Perfect Location, Book Your Gore Mtn. Trip Today! ★★★

📍 Pottersville

Find Your Perfect Stay in Chestertown by Travel Style

Guest Reviews on Chestertown Hotels

7.0
Excellent Community Rating
Real & verified guest reviews from around the world
G

Guest User

Other
Pine Tree Motel & Cabins ★★
"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"
★★★★★
2026-07-06
Q

Q4402MErichardh

Couple
The Fern Lodge ★★★★
"We visited Fern at the end of September for 6 nights. I have cancer and prior to the trip Wendy was as nice as could be - flexible and accommodating in every way. I wish I could say it stayed that way. A free boat ride on the lake is a feature of all stays. It started with her offer to take us on a private boat ride the next day, rather than have to go the day of arrival w others. We accepted her offer. I texted her 15 minutes prior to confirm & find out where to meet, and she had forgotten about it. Rather than apologize, which we would’ve understood and forgiven, she made up an excuse about the water being choppy and windy (it wasn’t) & texted “Tomorrow looks fabulous. Why don’t we do it then?” We had prior plans, it was our vacation! Her response “we will make it work, no worries.” She never followed up. I mentioned it to her the day before we left early PM. She said 5pm would work but it would be cold & windy, dress warm. We declined. She had forgotten again. No apology. Her assistant Sasha had a sour attitude the entire time we were there. Never a smile. You have to ask for toilet paper. They keep it locked up. What?! She actually questioned why we needed another roll! Like others, we had breakfast brought to our room. She would actually knock on our door to see if we were done because she wanted the tray back. We finally told her we’d bring it back when we were done. The room itself (pine room) had multiple problems. The fireplace was broken. A real letdown. Wendy tried to fix it and wasn’t successful. She claimed she didn’t know beforehand. Sorry but as the manager it’s her responsibility to test these things before every guest comes. We had 3 windows and one didn’t open at all. Again there was no accountability. Because of this, ventilation was lousy. We had turned on the A/C because of this and the firepit that was on most nights and caused very smoky air in our room. ASTHMATICS beware. Sasha reprimanded us because of this. “Why in the world did you put the air on when it’s comfortable outside?” Then the air leaked all over the dresser. There was no chair in the room - just a worn out couch. The heavy, stiff bedspread on the bed was old and unlikely to have been washed between guests. It would be too big a production for a small outfit to undertake. Which makes it very unsanitary. See attached photos of this and the carpet on the hard wood floor which has no padding making it extremely uncomfortable to sit on so if you’re eating breakfast inside your room it’s difficult. Photo of breakfast too In contrast to the bountiful breakfast shown on the website, we received very small amounts of food - ROTTEN berries, a piece of ham literally 1” big, 1/2 cup of scrambled eggs. The area itself has next to no place to eat unless you drive at least 20 minutes for pizza and the like, want to eat unhealthy bar food, or pay a fortune for a healthy meal at Friends Lake Inn. And a good supermarket? Good luck!! Lastly as we were more than ready to leave, "
★★★★☆
2023-10-12

Chestertown Travel Information

Power Plug & Voltage

120V/Type A/B

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Exchange Rate

1 CAD ≈ 0.73 USD

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Local Payment

Cards/ApplePay/Cash

📱

Connectivity

Verizon/AT&T/T-Mobile

More Information About Chestertown Hotels

Key Info

Details

Number of reviews

157

Total properties

19

Weekday Avg. Price

CAD 444

Weekend Avg. Price

CAD 447

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 586) and Pine Tree Motel & Cabins (from CAD 268) are popular choices.

  • What is the average price for hotels in Chestertown?

    The average price for hotels in Chestertown is CAD 444 for weekdays, and CAD 447 for weekends (Friday–Saturday).

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

    The Fern Lodge (from CAD 586) 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 586) 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 586) and Pine Tree Motel & Cabins (from CAD 268) are popular hotels with free Wi-Fi.

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