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.

Pine Tree Motel & Cabins
9.1 (36 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"

The Fern Lodge
9.7 (22 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."

3 bedroom cabin in Chestertown with hot tub, fireplace, fire pit, wifi, and more
10 (13 reviews)

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

📍 Chestertown

Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
10 (2 reviews)

Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George ★★★★

📍 Chestertown

Vintage Adk Cabin- Great Deal, Perfect Location, Book Your Gore Mtn. Trip Today!
9.2 (14 reviews)

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

📍 Pottersville

Camp RiverWood on the Hudson River
9.8 (4 reviews)

Camp RiverWood on the Hudson River ★★★

📍 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

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

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

📍 Chestertown

New Adirondack spacious cabin in the Lake George and Gore Mountain Area
9.8 (5 reviews)

New Adirondack spacious cabin in the Lake George and Gore Mountain Area ★★★

📍 Chestertown

Find Your Perfect Stay in Chestertown by Travel Style

Guest Reviews on Chestertown Hotels

9.0
Excellent Community Rating
Real & verified guest reviews from around the world
G

Guest User

Other
Pine Tree Motel & Cabins ★★
"We stayed three nights here in August and overall it met our expectations. Our rating is a 4.5 with the .5 being for the cabin being a little on the older side. However, the facilities are well maintained and the owners clearly take good care of them. The cabin was pretty snug with the queen bed taking up a lot of space but it was comfortable and clean as was the bathroom which was very good sized considering the overall cabin size. The owners are very friendly and staying here had a personal touch that you will not find everywhere. We would definitely stay here again."
★★★★★
2024-09-08
c

crkport

Couple
The Fern Lodge ★★★★
"There are a ton of places to stay in the Greater Lake George area. We love it here (third year) because it feels like we are visiting friends and family. The innkeeper — Wendy— is amazing and she makes an awesome breakfast! She also cooks up and delivers some great appetizers and beer/wine for happy hour! The rooms are delightful. All are different and enjoyable! LOVE this place!"
★★★★★
2023-10-26

Chestertown Travel Information

Power Plug & Voltage

120V/Type A/B

💵

Exchange Rate

1 CAD ≈ 0.72 USD

💳

Local Payment

Cards/ApplePay/Cash

📱

Connectivity

Verizon/AT&T/T-Mobile

More Information About Chestertown Hotels

Key Info

Details

Number of reviews

173

Total properties

24

Weekday Avg. Price

CAD 443

Weekend Avg. Price

CAD 451

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 578) and Pine Tree Motel & Cabins (from CAD 270) are popular choices.

  • What is the average price for hotels in Chestertown?

    The average price for hotels in Chestertown is CAD 443 for weekdays, and CAD 451 for weekends (Friday–Saturday).

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

    The Fern Lodge (from CAD 578) 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 578) 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 578) and Pine Tree Motel & Cabins (from CAD 270) are popular hotels with free Wi-Fi.

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