Photo by Julie Miller

Chestertown Hotels

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Sep 25 - Sep 26
Tomorrow
Sep 26 - Sep 27
This weekend
Sep 26 - Sep 28
Next weekend
Oct 3 - Oct 5

Filter by

Guest rating
Guest rating
Star rating

Top 10 trending Chestertown hotels

Our top choices for Chestertown hotels

Friends Lake Inn
1 bedroom, premium bedding, individually decorated

Friends Lake Inn

4.0 star property
8.8 out of 10, Excellent, (101)
"Staff was great. The inn is unique. Perfect!"
The price is P12,817
P14,226 total
includes taxes & fees
Sep 26 - Sep 27
Friends Lake Inn
Pine Tree Motel & Cabins
Exterior

Pine Tree Motel & Cabins

2.0 star property
9.2 out of 10, Wonderful, (141)
"Excellent location and staff was very friendly."
The price is P10,025
P11,128 total
includes taxes & fees
Sep 28 - Sep 29
Pine Tree Motel & Cabins
The Fern Lodge
Lake view

The Fern Lodge

3.5 star property
9.8 out of 10, Exceptional, (47)
"We had such a great experience the first night so we moved our plans and stayed a second, next time we will definitely stay even longer."
The Fern Lodge
Lodges At Cresthaven
Exterior

Lodges At Cresthaven

4.0 star property
9.4 out of 10, Exceptional, (501)
"Great place to stay!"
The price is P21,413
P23,768 total
includes taxes & fees
Sep 27 - Sep 28
Lodges At Cresthaven
Americas Best Value Inn & Suites Lake George
Living area

Americas Best Value Inn & Suites Lake George

2.5 star property
9.4 out of 10, Exceptional, (1015)
"Great trip & place to stay! "
The price is P4,526
P5,249 total
includes taxes & fees
Sep 30 - Oct 1
Americas Best Value Inn & Suites Lake George
The Stone Gate Resort
Private beach

The Stone Gate Resort

3.0 star property
9.6 out of 10, Exceptional, (91)
"Excellent stay, beautiful lake access. Friendly family owned staff."
The price is P9,564
P11,147 total
includes taxes & fees
Oct 8 - Oct 9
The Stone Gate Resort
Admiral Motel
Terrace/patio

Admiral Motel

2.5 star property
9.4 out of 10, Exceptional, (679)
"Great place to stay. Owners and staff are great."
The price is P5,207
P5,780 total
includes taxes & fees
Sep 26 - Sep 27
Admiral Motel
The Queensbury Hotel
Lobby

The Queensbury Hotel

3.0 star property
9.4 out of 10, Exceptional, (1372)
"Beautiful property with excellent restaurant on property!"
The price is P6,155
P6,832 total
includes taxes & fees
Oct 20 - Oct 21
The Queensbury Hotel
Trout House Village Resort
Living area

Trout House Village Resort

3.0 star property
9.6 out of 10, Exceptional, (14)
"Very friendly owner and beautiful views"
The price is P6,742
P8,921 total
includes taxes & fees
Oct 20 - Oct 21
Trout House Village Resort
The Inn of Lake George
Bar (on property)

The Inn of Lake George

2.5 star property
9.6 out of 10, Exceptional, (100)
"Beautiful and well kept inn, we had a great stay and vacation for 4th of July weekend! "
The Inn of Lake George
Fairfield Inn & Suites by Marriott Queensbury Glens Falls/Lake George Area
View from property

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

2.5 star property
9.6 out of 10, Exceptional, (449)
"The property was very clean and quiet the free breakfast was awesome hotel staff very friendly "
The price is P7,586
P8,420 total
includes taxes & fees
Oct 12 - Oct 13
Fairfield Inn & Suites by Marriott Queensbury Glens Falls/Lake George Area
Luzerne Court Motel
Exterior

Luzerne Court Motel

2.5 star property
9.4 out of 10, Exceptional, (313)
"This is our second time staying here and it was just perfect for our weekend getaway."
The price is P6,244
P6,931 total
includes taxes & fees
Sep 26 - Sep 27
Luzerne Court Motel
Holiday Inn Resort Lake George - Adirondack Area by IHG
Interior

Holiday Inn Resort Lake George - Adirondack Area by IHG

3.0 star property
9.2 out of 10, Wonderful, (1002)
"Wonderful property....highly recommend staying at the Lake George Holiday Inn Resort. "
The price is P6,781
P7,527 total
includes taxes & fees
Oct 26 - Oct 27
Holiday Inn Resort Lake George - Adirondack Area by IHG
Country Inn & Suites by Radisson, Lake George (Queensbury), NY
1 bedroom, premium bedding, pillowtop beds, individually decorated

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

3.0 star property
9.0 out of 10, Wonderful, (1231)
"Fine place to stay"
The price is P5,223
P5,798 total
includes taxes & fees
Sep 28 - Sep 29
Country Inn & Suites by Radisson, Lake George (Queensbury), NY
Heritage of Lake George
Property grounds

Heritage of Lake George

3.0 star property
9.0 out of 10, Wonderful, (667)
"Really good place to stay, family friendly and right on the lake George strip which is nice "
Heritage of Lake George
La Quinta Inn & Suites by Wyndham Lake George
Indoor pool

La Quinta Inn & Suites by Wyndham Lake George

3.0 star property
9.0 out of 10, Wonderful, (1688)
"Would stay there again"
The price is P5,794
P6,432 total
includes taxes & fees
Oct 20 - Oct 21
La Quinta Inn & Suites by Wyndham Lake George
Courtyard by Marriott Lake George
1 bedroom, premium bedding, desk, laptop workspace

Courtyard by Marriott Lake George

3.0 star property
9.2 out of 10, Wonderful, (1010)
"Great place to stay"
The price is P9,108
P10,110 total
includes taxes & fees
Oct 20 - Oct 21
Courtyard by Marriott Lake George
Home2 Suites by Hilton Queensbury Lake George
Premium bedding, pillowtop beds, in-room safe, desk

Home2 Suites by Hilton Queensbury Lake George

3.0 star property
9.2 out of 10, Wonderful, (813)
"The staff were excellent and very helpful."
The price is P9,568
P10,620 total
includes taxes & fees
Oct 19 - Oct 20
Home2 Suites by Hilton Queensbury Lake George
Mohican Resort Motel
Gazebo

Mohican Resort Motel

2.5 star property
9.0 out of 10, Wonderful, (154)
"Clean, staff very friendly, family friendly! Great place and would definitely book again!"
Mohican Resort Motel
Quality Inn Lake George
Lobby

Quality Inn Lake George

2.5 star property
9.2 out of 10, Wonderful, (668)
"Comfortable stay"
The price is P6,348
P7,046 total
includes taxes & fees
Oct 26 - Oct 27
Quality Inn 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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.

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.

See all hotels in Chestertown
Photo by Julie Miller
Open Photo by Julie Miller

Top Chestertown Hotel Reviews

Holiday Inn Resort Lake George - Adirondack Area by IHG

Holiday Inn Resort Lake George - Adirondack Area by IHG

10/10 Excellent
"Facility as a whole appears new. Very clean everywhere. Pool and hot tub were great. Restaurant and bar were busy and service was great. Rooms were very comfortable."
Nevada 1-night trip
Posted 1 day ago
Holiday Inn Resort Lake George - Adirondack Area by IHG

More cheap stays in Chestertown

More cheap stays in Chestertown

Baymont by Wyndham Queensbury / Lake George

Baymont by Wyndham Queensbury / Lake George

1 Abbey Ln, Queensbury, NY
The price is P4,239 per night from Sep 28 to Sep 29
P4,239
P4,705 total
Sep 28 - Sep 29
includes taxes & fees
7.2/10 Good! (1,030 reviews)

Frequently asked questions

Where is the best place to stay in Chestertown?

The Fern Lodge is a favorite property for Expedia customers. This B&B offers free breakfast and free parking. Other top choices based on reviews include Pine Tree Motel & Cabins and Friends Lake Inn. 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?

The Queensbury Hotel: Provides 2 restaurants, an indoor pool, and 2 bars. Lakefront Terrace Resort and The Georgian Lakeside Resort 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 120 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia