Where is the best place to stay in Chestertown?

Friends Lake Inn is one of the top choices for your stay based on our traveller data. This 4-star hotel offers a full-service spa and a restaurant. Other good options for your stay include Pine Tree Motel & Cabins and The Fern Lodge . See all available top hotels , or vacation rentals in Chestertown .

If I need to cancel my hotel reservation in Chestertown, will I receive a refund?

Yes, you'll find most room reservations are fully refundable if you cancel before the hotel’s cancellation deadline, which is often 24 or 48 hours before your arrival date. If you booked a non-refundable reservation, it might still be possible to cancel it and receive a refund within a 24-hour period of booking. Filter your search by free cancellation to find flexible hotel deals in Chestertown.

What's the best accommodation for a budget-friendly stay in Chestertown?

Based on reviews, Pine Tree Motel & Cabins is a popular 2-star property for our travellers looking for an economical choice, and features free WiFi and free parking. View all budget hotels in Chestertown .

What's the best place to stay for a family holiday in Chestertown?

Pine Tree Motel & Cabins is a property with free parking and free WiFi, and it's a top choice on Expedia for families. The Fern Lodge is another good option for your child-friendly holiday. Also, attractions in the area such as Garnet Hill Lodge and Ski Resort and House of Frankenstein Wax Museum are fun for children of all ages. Find more child-friendly accommodations in Chestertown .

What's the best hotel for a couple visiting Chestertown?

Friends Lake Inn is a favourite 4-star hotel for couples, and features a full-service spa and wedding services. Another choice for a romantic stay is The Fern Lodge . See all romantic hotels in Chestertown .

What's the best pet-friendly place to stay in Chestertown?

Pine Tree Motel & Cabins is a top property for people travelling with their pets and offers free WiFi for its human guests. See more pet-friendly hotel accommodations in Chestertown .

What's the best hotel for a beach holiday in Chestertown?

Pine Tree Motel & Cabins is a top beach property offering free WiFi and free parking, located within a short 11-minute walk of Loon Lake Beach . See more stays near the beach in Chestertown .

What's the best luxury accommodation option in Chestertown?

Friends Lake Inn is a 4-star hotel with a full-service spa and a terrace, and it's a popular choice for Expedia travellers looking for an elegant place to stay. Find more luxury hotels in Chestertown .

What's the best accommodation option for a trip to the slopes in Chestertown?

Based on our travel data, The Fern Lodge is a top 3.5-star B&B for a winter holiday, and features ski passes and private hot tubs. Friends Lake Inn is another good choice for your skiing trip. Those looking to ski or snowboard can spend their days at Gore Mountain Ski Resort.

What is the best spa hotel in Chestertown?

Friends Lake Inn is a top spa hotel featuring a bar and a restaurant. Treat yourself to a massage at the on-site spa. See all spa hotels in Chestertown .

What is staying in Chestertown like?

Visitors to Chestertown will definitely enjoy the lakeside setting. Tourists can also enjoy the city's coffee shops, forests and seafood restaurants. Top sights around the area include Gore Mountain Ski Resort and Outlets at Lake George . In Chestertown, there are 95 hotels and other accommodation options to choose from. Find out more about Chestertown .

What is there to see in Chestertown?

Natural beauty is on display at Hudson River , Loon Lake Beach and Loon Lake . You'll also find Gore Mountain Ski Resort and Outlets at Lake George in the area. Take a look at what more there is to see and do in Expedia's Chestertown guide .

What's the seasonal weather like in Chestertown?

The hottest months are usually July and August, with an average temperature of 18°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Chestertown are February, January, March and December, with each month seeing an average of 23 cm of snowfall.

TOP Hotels in Chestertown, NY

Friends Lake Inn

963 Friends Lake Rd, Chestertown, NY, 12817

2.29 km from city centre

4.4/5 Excellent! (58 reviews)

"We enjoyed everything about the property, especially the sauna. Staff is amazing especially Nicole, very vibrant and lively. Will definitely be back again."

Reviewed on 10 Apr 2022

Pine Tree Motel & Cabins

5537 State Route 8, Chestertown, NY, 12817

3.47 km from city centre

4.5/5 Wonderful! (90 reviews)

Cozy and Cute lodgings.

"Cozy, cute and clean lodgings. Owner was super friendly and beds were comfy. My daughter and I stayed here for a quick overnight. It’s conveniently located and set back off of Rt 8 in Chestertown. We had a quiet and restful stay."

Reviewed on 12 Oct 2021

The Fern Lodge

46 Fiddlehead Bay Rd., Chestertown, NY, 12817

2.15 km from city centre

4.9/5 Exceptional! (26 reviews)

"I would highly recommend The Fern Lodge. The is amazing. My husband describes it as a peaceful place. And it’s extremely clean. Sharon is great! She gave us a tour. We will definitely be back!!"

Reviewed on 14 Aug 2020

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The Loft at The Remington

6369 Main Street, Chestertown, NY, 12817

2.97 km from city centre

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Birchwood Cottages on Loon Lake

7157 U.S. 9, Chestertown, NY, 12817

6.51 km from city centre

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