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Tonight
Check prices in Chestertown for tonight, Oct 4 - Oct 5
Oct 4 - Oct 5
Tomorrow night
Check prices in Chestertown for tomorrow night, Oct 5 - Oct 6
Oct 5 - Oct 6
Next weekend
Check prices in Chestertown for next weekend, Oct 9 - Oct 11
Oct 9 - Oct 11

Most frequently booked Chestertown hotels

Pine Tree Motel & Cabins

Pine Tree Motel & Cabins

2 out of 5
5537 State Route 8 Chestertown NY
2.64 km from city centre
The price is CA $249 per night
CA $249
CA $277 total
Oct 5 - Oct 6
includes taxes & fees
Stay at this motel in Chestertown. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Loon Lake Beach and Loon Lake are located nearby.
Pet-friendly
Parking included
Friends Lake Inn

Friends Lake Inn

4 out of 5
963 Friends Lake Rd Chestertown NY
4.28 km from city centre
The price is CA $184 per night
CA $184
CA $204 total
Oct 27 - Oct 28
includes taxes & fees
Stay at this hotel in Chestertown. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Friends Lake and Loon Lake Beach are located nearby.
Parking included
Free WiFi
Elizabeth. 15 minutes to Lake George. Seasonal Heated Pool.

Elizabeth. 15 minutes to Lake George. Seasonal Heated Pool.

Chestertown NY
0.24 km from city centre
Get rates
Stay at this vacation home in Chestertown. Enjoy free WiFi, private pools, and a garden. Popular attractions Loon Lake Beach and Friends Lake are located nearby.
Pool
Kitchen
Great Escape Lodge & Indoor Waterpark

Great Escape Lodge & Indoor Waterpark

3.5 out of 5
89 Six Flags Dr Queensbury NY
34.47 km from city centre
The price is CA $145 per night
CA $145
CA $160 total
Oct 12 - Oct 13
includes taxes & fees
Book a stay at this family-friendly resort in Queensbury. Enjoy free WiFi, free parking, and 3 restaurants. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Great Escape and Fort William Henry Museum are located nearby.
Parking included
Free WiFi
La Quinta Inn & Suites by Wyndham Lake George

La Quinta Inn & Suites by Wyndham Lake George

3 out of 5
1533 US-9 Lake George NY
Free cancellation
Reserve now, pay when you stay
32.4 km from city centre
The price is CA $120 per night
CA $120
CA $133 total
Oct 28 - Oct 29
includes taxes & fees
Book a stay at this family-friendly hotel in Lake George. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Great Escape and Fort William Henry Museum are located nearby.
Pool
Hot tub
Baymont by Wyndham Queensbury / Lake George

Baymont by Wyndham Queensbury / Lake George

2.5 out of 5
1 Abbey Ln Queensbury NY
Free cancellation
Reserve now, pay when you stay
37.5 km from city centre
The price is CA $106 per night
CA $106
CA $118 total
Oct 5 - Oct 6
includes taxes & fees
Book a stay at this business-friendly hotel in Queensbury. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Great Escape and Regal Aviation Mall are located nearby.
Pool
Breakfast included
Adirondack Retreat Inn & Suites

Adirondack Retreat Inn & Suites

2.5 out of 5
435 Canada Street Lake George NY
25.7 km from city centre
The price is CA $130 per night
CA $130
CA $150 total
Oct 7 - Oct 8
includes taxes & fees
Book a stay at this family-friendly motel in Lake George. Enjoy free WiFi, free parking, and an area shuttle (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Fort William Henry Museum and Great Escape are located nearby.
Pool
Parking included
The Georgian Lakeside Resort

The Georgian Lakeside Resort

2.5 out of 5
384 Canada Street Lake George NY
25.91 km from city centre
The price is CA $141 per night
CA $141
CA $157 total
Oct 16 - Oct 17
includes taxes & fees
Book a stay at this beach hotel in Lake George. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the pool and the restaurant in our reviews. Popular attractions Fort William Henry Museum and Great Escape are located nearby.
On private beach
Pool
The Queensbury Hotel

The Queensbury Hotel

3 out of 5
88 Ridge St Glens Falls NY
Free cancellation
Reserve now, pay when you stay
40 km from city centre
The price is CA $159 per night
CA $159
CA $177 total
Oct 12 - Oct 13
includes taxes & fees
Book a stay at this business-friendly hotel in Glens Falls. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Great Escape and Charles R. Wood Theater are located nearby.
Pool
Hot tub
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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.

Top family friendly Chestertown hotel deals

Pine Tree Motel & Cabins

Pine Tree Motel & Cabins

5537 State Route 8 Chestertown NY
The price is CA $249 per night from Oct 5 to Oct 6
CA $249
CA $277 total
Oct 5 - Oct 6
includes taxes & fees
9.2/10 Wonderful! (169 reviews)

Chestertown hotels essential information

Accommodation
1,634 hotels
Lowest Price
CA $118
Highest Price
CA $634
Popular hotels
Pine Tree Motel & Cabins, Friends Lake Inn, Elizabeth. 15 minutes to Lake George. Seasonal Heated Pool., Great Escape Lodge & Indoor Waterpark, La Quinta Inn & Suites by Wyndham Lake George, Baymont by Wyndham Queensbury / Lake George, Adirondack Retreat Inn & Suites, The Georgian Lakeside Resort, The Queensbury Hotel

Frequently asked questions

What are the top kid-friendly hotels in Chestertown?
Take some of the stress out of traveling with kids by choosing a family-friendly hotel in Chestertown. From useful amenities to additional services, these stays feature perks that'll help make your visit run like a dream: Historic Greek Revival style home w/ screened in porch -near attractions! will help make your trip the most memorable one yet. It features an assortment of conveniences geared toward families, such as a water park and a nearby theme park. Otherwise, spend your nights enjoying the comforts of The Loft at The Remington. Make the most of complimentary breakfast, extra bedding and more here.
Where can I find cheap hotels in Chestertown?
At Travelocity you'll find really nice hotels in Chestertown at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Chestertown rather than in Chestertown. We may find you even better rates, too.
How do I find the best Chestertown hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Chestertown then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Chestertown?
The cheapest hotel in Chestertown is CA $118 This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Chestertown?
There are 1,634 hotels in Chestertown on Travelocity.
What are the best hotels in Chestertown?
Chestertown has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Chestertown for you!
When is the best time to visit Chestertown?
If you want the joy of a fun-filled trip in peak season, visit Chestertown during January, July and August. If you'd prefer the peace of off-season, book a stay during quieter months, such as February, November and December.
When is the cheapest time to stay in Chestertown?
Based on historic data is usually the cheapest month to visit Chestertown. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Chestertown?
There are multiple hotels in Chestertown that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Chestertown. We have plenty of kid-friendly hotels in Chestertown to choose from on Travelocity!
Why book a hotel in Chestertown through Travelocity?
Because we have the top hotels in Chestertown! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Chestertown on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Chestertown hotel reviews by fellow wanderers

La Quinta Inn & Suites by Wyndham Lake George

La Quinta Inn & Suites by Wyndham Lake George

5 out of 5
Posted 8 hours ago
Travelocity Verified Review
"Great for families. Pool was great. Coin wash machines a plus. Playground in the back kept kids additionally entertained. Close to Lake George and activities"
A verified traveller stayed at La Quinta Inn & Suites by Wyndham Lake George
La Quinta Inn & Suites by Wyndham Lake George