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Tonight
Check prices in Chester for tonight, Jul 28 - Jul 29
Jul 28 - Jul 29
Tomorrow night
Check prices in Chester for tomorrow night, Jul 29 - Jul 30
Jul 29 - Jul 30
This weekend
Check prices in Chester for this weekend, Jul 31 - Aug 2
Jul 31 - Aug 2
Next weekend
Check prices in Chester for next weekend, Aug 7 - Aug 9
Aug 7 - Aug 9

Most frequently booked Chester hotels

Fullerton Inn

Fullerton Inn

2.5 out of 5
40 The Common Chester VT
Free cancellation
Reserve now, pay when you stay
0.39 km from city centre
The price is CA $224 per night
CA $224
CA $244 total
Jul 29 - Jul 30
includes taxes & fees
Stay at this inn in Chester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions DaVallia Art & Accents and Bonnie's Bundles Dolls are located nearby.
Breakfast included
Parking included
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
40.53 km from city centre
The price is CA $620 per night
CA $620
CA $744 total
Aug 16 - Aug 17
includes taxes & fees
Book a stay at this luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Quechee Gorge Bridge and Middle Covered Bridge are located nearby.
Pool
Hot tub
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

2.5 out of 5
175 Key Rd Keene NH
Free cancellation
Reserve now, pay when you stay
44.68 km from city centre
The price is CA $182 per night
CA $182
CA $197 total
Jul 29 - Jul 30
includes taxes & fees
Book a stay at this business-friendly hotel in Keene. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Ashuelot River and Cheshire Children's Museum are located nearby.
Pool
Breakfast included
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4 out of 5
3835 Main St. Manchester VT
40.02 km from city centre
The price is CA $279 per night
CA $279
CA $366 total
Aug 11 - Aug 12
includes taxes & fees
Book a stay at this golf hotel in Manchester. Enjoy an outdoor pool, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. Popular attractions Golf Club at Equinox and American Museum of Fly Fishing are located nearby.
Pool
Pet-friendly
Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

3 out of 5
89 Grand Summit Way West Dover VT
Free cancellation
40.96 km from city centre
The price is CA $212 per night
CA $212
CA $253 total
Aug 26 - Aug 27
includes taxes & fees
Book a stay at this spa resort in West Dover. Enjoy free WiFi, a full-service spa, and a free area shuttle. Popular attractions Mount Snow and Tumbleweed Ski Lift are located nearby.
Spa
Free WiFi
On The River Inn

On The River Inn

4 out of 5
1653 West Woodstock Road Woodstock VT
38.7 km from city centre
The price is CA $311 per night
CA $311
CA $373 total
Aug 17 - Aug 18
includes taxes & fees
Book a stay at this family-friendly hotel in Woodstock. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Union Arena Community Center and Five Elm Arches are located nearby.
Pool
Hot tub
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

3 out of 5
401 Winchester St Keene NH
Free cancellation
Reserve now, pay when you stay
45.16 km from city centre
The price is CA $196 per night
CA $196
CA $213 total
Jul 29 - Jul 30
includes taxes & fees
Book a stay at this business-friendly hotel in Keene. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Ashuelot River and Redfern Arts Center are located nearby.
Pool
Breakfast included
Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street Brattleboro VT
Free cancellation
Reserve now, pay when you stay
45.86 km from city centre
The price is CA $166 per night
CA $166
CA $182 total
Aug 9 - Aug 10
includes taxes & fees
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and conference space. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Latchis Theatre and Brattleboro Museum & Art Center are located nearby.
Pet-friendly
Parking included
The Palmer House Resort, an Ascend Collection Hotel

The Palmer House Resort, an Ascend Collection Hotel

3 out of 5
5383 Main St Manchester Center VT
Free cancellation
37.85 km from city centre
The price is CA $164 per night
CA $164
CA $203 total
Aug 4 - Aug 5
includes taxes & fees
Book a stay at this golf hotel in Manchester Center. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Lye Brook Falls and Dana L. Thompson Memorial Park are located nearby.
Pool
Hot tub
Don't see what you're looking for?
See all available properties in Chester
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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 cheap Chester hotel deals

Motel in the Meadow

Motel in the Meadow

936 VT Route 11 West Chester VT
Get rates
8.4/10 Very good! (71 reviews)

Top hotels in Chester for Extended Stay

Pamper Yourself at Jackson Gore

Pamper Yourself at Jackson Gore

Ludlow VT
9.8/10 Exceptional! (22 reviews)
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.

Chester hotels essential information

Accommodation
3,078 hotels
Lowest Price
CA $182
Highest Price
CA $744
Popular hotels
Fullerton Inn, Woodstock Inn & Resort, Keene Elm City Hotel, an Ascend Collection Hotel, Kimpton Taconic Hotel by IHG, Grand Summit Resort, A Vail Resorts Property, On The River Inn, Best Western Plus Keene Hotel, Latchis Hotel, The Palmer House Resort, an Ascend Collection Hotel

Frequently asked questions

What are the top kid-friendly hotels in Chester?
Family vacations are where lifelong memories are made, but traveling with children can be tricky. These kid-friendly Chester hotels offer perks designed to keep old and young alike relaxed and happy: You'll be well taken care of at Charming Farmhouse in Chester. It comes with a fireplace, pet-friendly facilities and a flair for making families feel welcome. Otherwise, spend your nights enjoying the comforts of Rose Arbour Bed & Breakfast. Take advantage of complimentary breakfast, a cafe and more here.
Where can I find cheap hotels in Chester?
At Travelocity you'll find really nice hotels in Chester 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 Chester rather than in Chester. We may find you even better rates, too.
How do I find the best Chester hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Chester 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 Chester?
The cheapest hotel in Chester is CA $182 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 Chester?
There are 3,078 hotels in Chester on Travelocity.
What are the best hotels in Chester?
Chester 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 Chester for you!
When is the best time to visit Chester?
If you want the joy of a fun-filled trip in peak season, visit Chester during December, January and February. If you'd prefer the peace of off-season, book a stay during quieter months, such as March, April and August.
When is the cheapest time to stay in Chester?
Based on historic data is usually the cheapest month to visit Chester. 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 Chester?
There are multiple hotels in Chester 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 Chester. We have plenty of kid-friendly hotels in Chester to choose from on Travelocity!
Why book a hotel in Chester through Travelocity?
Because we have the top hotels in Chester! 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 Chester 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 Chester hotel reviews by fellow wanderers

On The River Inn

On The River Inn

5 out of 5
Posted 7 hours ago
Travelocity Verified Review
"Very well-maintained property and nice guest rooms and dining room/bar is beautiful. The country breakfast was also a plus. Would definitely come back here!"
A verified traveller stayed at On The River Inn
On The River Inn