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Tonight
Check prices in Chester for tonight, Oct 27 - Oct 28
Oct 27 - Oct 28
Tomorrow night
Check prices in Chester for tomorrow night, Oct 28 - Oct 29
Oct 28 - Oct 29
This weekend
Check prices in Chester for this weekend, Oct 30 - Nov 1
Oct 30 - Nov 1
Next weekend
Check prices in Chester for next weekend, Nov 6 - Nov 8
Nov 6 - Nov 8

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 $181 per night
CA $181
CA $197 total
Nov 10 - Nov 11
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
Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

3 out of 5
698 VT-11 Chester VT
2.35 km from city centre
The price is CA $252 per night
CA $252
CA $274 total
Nov 16 - Nov 17
includes taxes & fees
Stay at this B&B in Chester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Bonnie's Bundles Dolls and DaVallia Art & Accents are located nearby.
Breakfast included
Parking included
Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area

Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area

Chester VT
9.07 km from city centre
Get rates
Stay at this cabin in Chester. Enjoy free WiFi, an in-room coffeemaker, and in-room fireplaces. Popular attractions Okemo Mountain Resort and Phineas Gage Memorial are located nearby.
Kitchen
Pet-friendly
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 $517 per night
CA $517
CA $630 total
Nov 16 - Nov 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
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 $221 per night
CA $221
CA $265 total
Nov 2 - Nov 3
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
Colonial Motel

Colonial Motel

3 out of 5
889 Putney Rd Brattleboro VT
Free cancellation
Reserve now, pay when you stay
42.82 km from city centre
The price is CA $120 per night
CA $120
CA $132 total
Nov 2 - Nov 3
includes taxes & fees
Book a stay at this business-friendly motel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Brattleboro Bowl and New England Center for Circus Arts are located nearby.
Breakfast included
Pet-friendly
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
111 Jackson Gore Road Ludlow VT
Free cancellation
Reserve now, pay when you stay
20.32 km from city centre
The price is CA $259 per night
CA $259
CA $314 total
Nov 18 - Nov 19
includes taxes & fees
Book a stay at this ski hotel in Ludlow. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Okemo Mountain Resort and Timber Ripper Mountain Coaster are located nearby.
Pool
Hot tub
Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

2 out of 5
3 Ash Brook Road Keene NH
Free cancellation
Reserve now, pay when you stay
44.39 km from city centre
The price is CA $132 per night
CA $132
CA $143 total
Oct 29 - Oct 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 helpful staff in our reviews. Popular attractions Ashuelot River and Cheshire Children's Museum are located nearby.
Breakfast included
Pet-friendly
Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow

3 out of 5
270 Handle Rd West Dover VT
41.12 km from city centre
The price is CA $124 per night
CA $124
CA $137 total
Oct 28 - Oct 29
includes taxes & fees
Book a stay at this ski hotel in West Dover. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Mount Snow and Heavy Metal Ski Lift 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

Explore the upper valley from this spacious Claremont Home

Explore the upper valley from this spacious Claremont Home

Claremont NH
The price is CA $420 per night from Oct 29 to Oct 30
CA $420
CA $515 total
Oct 29 - Oct 30
includes taxes & fees
10/10 Exceptional! (1 review)
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
3,134 hotels
Lowest Price
CA $132
Highest Price
CA $630
Popular hotels
Fullerton Inn, Stone Hearth Inn and Eatery, Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area, Woodstock Inn & Resort, Grand Summit Resort, A Vail Resorts Property, Colonial Motel, Jackson Gore Village, A Vail Resorts Property, Days Inn by Wyndham Keene NH, Hideaway Inn Mt. Snow

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 $132 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 3,134 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

The Equinox Golf Resort And Spa

The Equinox Golf Resort And Spa

5 out of 5
Posted 21 hours ago
Travelocity Verified Review
"Had a great girls weekend! The staff were amazing especially Adam and Jaden! The spa amenities were great- we especially loved the outdoor hot tub. Would 100% come back"
A verified traveller stayed at The Equinox Golf Resort And Spa
The Equinox Golf Resort And Spa