Photo by Julie Miller

Find hotels in Chestertown, NY from SAR 240

    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
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Filter by

Guest rating
Guest rating
Star rating

Compare 1,553 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Doray Motel

2.0 star property
8.4 out of 10, Very Good, (163)
"Location was great You can walk to any place :lake, store restaurant Also by car you can explore many places if you like nature or shopping Check little towns around Lake George Town."
The price is SAR 334
SAR 371 total
includes taxes & fees
27 Jul - 28 Jul
Doray Motel

Fran Cove Motel

2.0 star property
7.8 out of 10, Good, (301)
"Good price, comfortable bed, AC worked, good size refrigerator, trolley stop into town. Needs updating, towels in poor condition."
The price is SAR 240
SAR 274 total
includes taxes & fees
28 Jul - 29 Jul
Fran Cove Motel

Brookside Motel

2.5 star property
8.6 out of 10, Excellent, (617)
"There was a bit of a mix up with payment and the owner took care of everything with kindness and courtesy. We needed to leave early due to illness and they continued to be courteous. We will definitely be going back and staying at the Brookside. "
The price is SAR 315
SAR 350 total
includes taxes & fees
27 Jul - 28 Jul
Brookside Motel

Pine Tree Motel & Cabins

2.0 star property
9.2 out of 10, Wonderful, (130)
"Excellent location and staff was very friendly."
The price is SAR 656
SAR 729 total
includes taxes & fees
24 Jul - 25 Jul
Pine Tree Motel & Cabins

Friends Lake Inn

4.0 star property
8.8 out of 10, Excellent, (90)
"Quiet lodging and friendly staff"
The price is SAR 837
SAR 929 total
includes taxes & fees
24 Jul - 25 Jul
Friends Lake Inn

The Fern Lodge

3.5 star property
9.8 out of 10, Exceptional, (46)
"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

Silver Bay YMCA Inn and Conference Center

3.0 star property
8.6 out of 10, Excellent, (98)
"Beautiful area , very close to the lake . "
The price is SAR 571
SAR 633 total
includes taxes & fees
18 Aug - 19 Aug
Silver Bay YMCA Inn and Conference Center

Depe Dene Lakeside Resort

2.0 star property
8.8 out of 10, Excellent, (325)
"Great stay!"
Depe Dene Lakeside Resort

Windsor Motel

2.5 star property
7.4 out of 10, Good, (213)
"Great place"
The price is SAR 278
SAR 308 total
includes taxes & fees
24 Jul - 25 Jul
Windsor Motel

Countryside Inn

2.5 star property
6.8 out of 10, (179)
"Very nice for a small family just what you need perfectly In between lake and shopping centers. Not fancy don’t expect that but decently worth what you pay. "
The price is SAR 296
SAR 329 total
includes taxes & fees
24 Jul - 25 Jul
Countryside Inn

Pinebrook Motel

2.0 star property
7.4 out of 10, Good, (176)
"I thoroughly enjoyed my two night Stay at this motel."
The price is SAR 384
SAR 427 total
includes taxes & fees
27 Jul - 28 Jul
Pinebrook Motel

Red Roof Inn Queensbury

2.5 star property
7.0 out of 10, Good, (1009)
"Just an average hotel, a place to stay nothing fancy nothing extra. If you need a place to sleep and nothing else then this place is fine. "
The price is SAR 279
SAR 310 total
includes taxes & fees
4 Aug - 5 Aug
Red Roof Inn Queensbury

The Queensbury Hotel

3.0 star property
9.2 out of 10, Wonderful, (1284)
"Nice property, we stay every time we visit the area. Love that it's dog friendly, and conveniently located."
The Queensbury Hotel

Amber Lantern Lake George Motel and Cottage Rentals

2.0 star property
8.4 out of 10, Very Good, (288)
"The room was very nice, clean and had everything we needed. We had an efficiency. "
Amber Lantern Lake George Motel and Cottage Rentals

Seven Dwarfs Motel and Cabins

2.0 star property
7.4 out of 10, Good, (155)
"I have been coming here for quick getaways for several years. Love the brown cabins, so peaceful here, with the stream running in back of the homey cabin. "
The price is SAR 427
SAR 474 total
includes taxes & fees
27 Jul - 28 Jul
Seven Dwarfs Motel and Cabins

Barberry Court Motel

2.5 star property
7.0 out of 10, Good, (100)
"We had a great stay here. Perfect for a little get away! "
The price is SAR 334
SAR 371 total
includes taxes & fees
27 Jul - 28 Jul
Barberry Court Motel

Lake View Inn

2.0 star property
5.6 out of 10, (285)
"We had a great time staying here. The rooms were clean and the owners were responsive. The cleaner of our room was friendly and did a great job. Great location as you can walk to the beach and the strip. Plan to stay again next summer! "
The price is SAR 279
SAR 393 total
includes taxes & fees
31 Jul - 1 Aug
Lake View Inn

Baymont by Wyndham Queensbury / Lake George

2.5 star property
7.4 out of 10, Good, (1014)
" Large, dated hotel, and secluded, clean rooms. Ok for one night, as we stopped over Lake George for the night. "
The price is SAR 284
SAR 315 total
includes taxes & fees
3 Aug - 4 Aug
Baymont by Wyndham Queensbury / Lake George

Studio Motel

2.0 star property
8.6 out of 10, Excellent, (915)
"I would stay again ! "
The price is SAR 371
SAR 425 total
includes taxes & fees
24 Jul - 25 Jul
Studio Motel

The Inn of Lake George

2.5 star property
9.8 out of 10, Exceptional, (92)
"Beautiful and well kept inn, we had a great stay and vacation for 4th of July weekend! "
The Inn of 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 map

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

Loon Lake Beach

Loon Lake Beach

If a restful vacation is part of your travel plans, Loon Lake Beach might be the perfect place to seek out during your trip to Chestertown. While you're in the area, stroll along the lakeside.

Learn more about Chestertown

Get away to secluded Chestertown! Enjoy the lake views, coffee, and horseback riding.

A winter scene
Photo by Julie Miller
Open Photo by Julie Miller

Top Chestertown Hotel 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.

What are some of the best vacation rentals that Chestertown has to offer?

Family Friendly - Pet Friendly : This vacation home rental outside of Chestertown is located on a lake and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. See all 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.

What's the best pet-friendly accommodation in Chestertown?

Pine Tree Motel & Cabins is a top pet-friendly option for your stay. Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing is another good option if you're bringing your pet along. 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?

Best Western of Lake George: Hotel located near Lake George. Provides daily, an outdoor pool, and free self parking. The Queensbury Hotel and Lakefront Terrace Resort are two additional hotels that feature an onsite pool. View all hotels with pools in Chestertown.

What's the most popular hotel in Chestertown with an on-site water park or a water park nearby?
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. A top sight in the area is Lake George. In Chestertown, there are 121 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. Additionally, you'll find Lake George in the area. 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.