A waterfront town with a pier, dock, and several buildings.

Find hotels in Chestertown, NY from ā‚©99,961

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks

Filter by

Property class

Guest rating

Selecting then applying a filter from this group will update the results on a new page

Our top choices for Chestertown hotels

1. Friends Lake Inn

Friends Lake Inn
4.0 star property
Chestertown
8.6 out of 10, Excellent, (137 reviews)
"Great breakfast, very friendly staff and beautiful place"
United States
Pierre
The price is ā‚©157,612
ā‚©174,934 total
includes taxes & fees
Nov 9 - Nov 10
Friends Lake Inn

2. Holiday Inn Resort Lake George - Adirondack Area by IHG

Holiday Inn Resort Lake George - Adirondack Area by IHG
3.0 star property
Lake George
9.4 out of 10, Exceptional, (1,001 reviews)
"Great family place to stay. Clean and well maintained hotel. Very helpful staff. Amazing restaurant with very helpful staff and delicious food."
United States
HAGOP
The price is ā‚©161,548
ā‚©179,319 total
includes taxes & fees
Nov 8 - Nov 9
Holiday Inn Resort Lake George - Adirondack Area by IHG

3. Comfort Inn & Suites Lake George

Comfort Inn & Suites Lake George
2.5 star property
Lake George
8.8 out of 10, Excellent, (1,001 reviews)
"We liked overall stay and had a good experience."
United States
Manish
The price is ā‚©134,425
ā‚©149,212 total
includes taxes & fees
Nov 15 - Nov 16
Comfort Inn & Suites Lake George

4. Lodge at Schroon Lake

Lodge at Schroon Lake
3.0 star property
Schroon Lake
9.0 out of 10, Wonderful, (587 reviews)
"Clean and well-kept hotel with an Adirondack feel and a view of Schroon lake."
United States
Elizabeth
The price is ā‚©167,386
ā‚©233,632 total
includes taxes & fees
Nov 8 - Nov 9
Lodge at Schroon Lake

5. The Alpine Lodge

The Alpine Lodge
3.0 star property
North Creek
9.0 out of 10, Wonderful, (714 reviews)
"Absolutely adorable place! Comfy and cozy."
United States
Patricia
The price is ā‚©123,585
ā‚©151,692 total
includes taxes & fees
Nov 9 - Nov 10
The Alpine Lodge

6. Country Inn & Suites by Radisson, Lake George (Queensbury), NY

Country Inn & Suites by Radisson, Lake George (Queensbury), NY
3.0 star property
Queensbury
9.0 out of 10, Wonderful, (1,563 reviews)
"Great place to stay Love the fire pit outside."
United States
Nicole
The price is ā‚©106,147
ā‚©117,824 total
includes taxes & fees
Dec 6 - Dec 7
Country Inn & Suites by Radisson, Lake George (Queensbury), NY

7. Courtyard by Marriott Lake George

Courtyard by Marriott Lake George
3.0 star property
Lake George
9.2 out of 10, Wonderful, (1,000 reviews)
"Great place to stay"
United States
Luann
The price is ā‚©151,503
ā‚©168,168 total
includes taxes & fees
Nov 9 - Nov 10
Courtyard by Marriott Lake George

8. Lodges At Cresthaven

Lodges At Cresthaven
4.0 star property
Lake George
9.4 out of 10, Exceptional, (667 reviews)
"amazing place"
United States
Faruk
The price is ā‚©122,947
ā‚©136,471 total
includes taxes & fees
Nov 8 - Nov 9
Lodges At Cresthaven

9. Fairfield Inn & Suites by Marriott Queensbury Glens Falls/Lake George Area

Fairfield Inn & Suites by Marriott Queensbury Glens Falls/Lake George Area
3.0 star property
Queensbury
9.6 out of 10, Exceptional, (560 reviews)
"I love it here I try to come every year it's way cleaner than most hotels I've stayed at everything was wonderful"
United States
Katheren
The price is ā‚©137,316
ā‚©152,421 total
includes taxes & fees
Nov 15 - Nov 16
Fairfield Inn & Suites by Marriott Queensbury Glens Falls/Lake George Area

10. Hampton Inn & Suites Lake George

Hampton Inn & Suites Lake George
2.5 star property
Lake George
9.0 out of 10, Wonderful, (1,003 reviews)
"Great place to stay."
United States
PATRICIA
The price is ā‚©137,316
ā‚©152,421 total
includes taxes & fees
Dec 3 - Dec 4
Hampton Inn & Suites Lake George

11. The Queensbury Hotel

The Queensbury Hotel
3.0 star property
Glens Falls
9.4 out of 10, Exceptional, (1,669 reviews)
"Great place to stay"
United States
Kirk
The price is ā‚©149,330
ā‚©165,758 total
includes taxes & fees
Dec 6 - Dec 7
The Queensbury Hotel

12. Holiday Inn Express Queensbury - Lake George Area by IHG

Holiday Inn Express Queensbury - Lake George Area by IHG
2.5 star property
Queensbury
9.0 out of 10, Wonderful, (1,000 reviews)
"Great hotel, good breakfast, perfect location."
United States
Gary
The price is ā‚©118,107
ā‚©131,100 total
includes taxes & fees
Dec 6 - Dec 7
Holiday Inn Express Queensbury - Lake George Area by IHG

13. Quality Inn Lake George

Quality Inn Lake George
2.5 star property
Lake George
9.2 out of 10, Wonderful, (749 reviews)
"The hotel was very clean and comfortable. I would stay there again"
United States
Laura
The price is ā‚©176,414
ā‚©195,827 total
includes taxes & fees
Nov 8 - Nov 9
Quality Inn Lake George

14. Fort William Henry Hotel and Conference Center

Fort William Henry Hotel and Conference Center
3.0 star property
Lake George
8.6 out of 10, Excellent, (1,002 reviews)
"Great location"
United States
Cynthia
The price is ā‚©137,786
ā‚©178,735 total
includes taxes & fees
Nov 13 - Nov 14
Fort William Henry Hotel and Conference Center

15. Skyline Hotel Lake George

Skyline Hotel Lake George
2.5 star property
Lake George
7.4 out of 10, Good, (1,001 reviews)
"The pool was closed......but everything else was great. Great breakfast food. Will stay there again."
United States
Steven
The price is ā‚©98,083
ā‚©108,874 total
includes taxes & fees
Nov 15 - Nov 16
Skyline Hotel Lake George

16. Super 8 by Wyndham Lake George/Warrensburg Area

Super 8 by Wyndham Lake George/Warrensburg Area
2.5 star property
Lake George
8.6 out of 10, Excellent, (1,002 reviews)
"Reasonably nice room at a fair price."
United States
Robert
The price is ā‚©90,054
ā‚©99,961 total
includes taxes & fees
Nov 8 - Nov 9
Super 8 by Wyndham Lake George/Warrensburg Area

17. Gore Mountain Lodge

Gore Mountain Lodge
2.0 star property
North Creek
9.2 out of 10, Wonderful, (221 reviews)
"What a wonderful family owned treasure in a fabulous location. Can’t wait to go back. Ty!!"
United States
Jennifer
The price is ā‚©182,047
ā‚©202,057 total
includes taxes & fees
Nov 9 - Nov 10
Gore Mountain Lodge

18. La Quinta Inn & Suites by Wyndham Lake George

La Quinta Inn & Suites by Wyndham Lake George
3.0 star property
Lake George
8.6 out of 10, Excellent, (1,719 reviews)
"Great stay"
United States
Philip
The price is ā‚©114,238
ā‚©126,803 total
includes taxes & fees
Nov 9 - Nov 10
La Quinta Inn & Suites by Wyndham Lake George

19. Spark by Hilton Lake George Outlets

Spark by Hilton Lake George Outlets
2.5 star property
Lake George
8.2 out of 10, Very good, (1,003 reviews)
"Very comfortable beds."
United States
Kenneth
The price is ā‚©104,911
ā‚©116,450 total
includes taxes & fees
Nov 12 - Nov 13
Spark by Hilton Lake George Outlets

20. Home2 Suites by Hilton Queensbury Lake George

Home2 Suites by Hilton Queensbury Lake George
3.0 star property
Queensbury
9.2 out of 10, Wonderful, (923 reviews)
"Great room great staff best best breakfast We will be back next year"
United States
Patrick
The price is ā‚©143,602
ā‚©159,398 total
includes taxes & fees
Nov 15 - Nov 16
Home2 Suites by Hilton Queensbury Lake George
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Where to stay in Chestertown

Find the best Chestertown areas and neighborhoods for the activities you enjoy most.

Chester Shores

When in Chester Shores, you can plan a visit to Loon Lake Beach and Loon Lake, some noteworthy sights in the nearby area.

Stay near popular Chestertown attractions

Learn more about Chestertown

Nestled in the Adirondacks, this charming town offers hiking trails and kayaking on Friends Lake during summer months. Winter visitors can hit the slopes at nearby Gore Mountain in North Creek or explore the Natural Stone Bridge and Caves in Pottersville.

A waterfront town with a pier, dock, and several buildings.

Top Chestertown Hotel Reviews

More cheap stays in Chestertown

Frequently asked questions

Where is the best place to stay in Chestertown?
Based on Expedia's traveler preferences, Pine Tree Motel & Cabins is a top place to stay in Chestertown. Two other choices for your visit to the area are Great Escape Lodge & Indoor Waterpark and La Quinta Inn & Suites by Wyndham Lake George. 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 that most hotel room reservations are refundable provided that you cancel prior to the hotel's cancellation deadline, which often is within 24-48 hours of check in. If you have a non-refundable reservation, it might still be possible to cancel it and be given a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Chestertown.
Where can I learn more about changing or cancelling my trip to Chestertown?
For more details about changing or cancelling your trip to Chestertown, head over to our customer service page.
What's the best LGBTQ-friendly place to stay in Chestertown?
Pine Tree Motel & Cabins is one of the top choices for those in the LGBT community. See all available hotels listed as LGBTQ-friendly in Chestertown.
What's the best pet-friendly accommodation in Chestertown?
Pine Tree Motel & Cabins is a top pet-friendly option for your stay. See more pet-friendly hotel accommodations in Chestertown.
What's the best hotel for a beach vacation in Chestertown?
The Fern Lodge is a top beach B&B with free breakfast and 8 hot tubs, and it's located close to Loon Lake Beach. See more stays near the beach in Chestertown.
What are some accommodations with pools in Chestertown?
La Quinta Inn & Suites by Wyndham Lake George: Hotel located near Great Escape. Features buffet, an indoor pool, and free self parking. The Georgian Lakeside Resort and The Queensbury Hotel are two additional hotels that feature an onsite pool. View all hotels with pools in Chestertown.
What's the best hotel for staying near Albany International Airport (ALB)?
Albany Airport Inn and Suites is a popular 3-star hotel featuring free breakfast and an outdoor pool. It's located a short 1.2 mi (2 km) from Albany Intl. Airport. Other places to stay close to the airport are Hilton Garden Inn Albany Airport and Red Lion Hotel Albany.
What is staying in Chestertown like?
Visitors to Chestertown are sure to enjoy the lakeside setting. Tourists can also enjoy the city's coffeehouses, forests, and seafood restaurants. In Chestertown, there are 115 hotels and other accommodations to choose from. Find out more about Chestertown.
What should I see while I'm in Chestertown?
Natural beauty is on display at Loon Lake Beach, Friends Lake, and Loon Lake. A couple of additional sights to add to your agenda are Hudson River and Tripp Pond. Check out what more to see and do in Expedia's Chestertown guide.
What's the weather like in Chestertown?
The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Chestertown are January, March, November, and December, with each month seeing an average of 13 inches of snowfall.