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Check prices in Chester for tonight, Oct 2 - Oct 3
Oct 2 - Oct 3
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Check prices in Chester for tomorrow night, Oct 3 - Oct 4
Oct 3 - Oct 4
This weekend
Check prices in Chester for this weekend, Oct 2 - Oct 4
Oct 2 - Oct 4

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 $212 per night
CA $212
CA $231 total
Nov 1 - Nov 2
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
Free cancellation
Reserve now, pay when you stay
2.35 km from city centre
The price is CA $369 per night
CA $369
CA $402 total
Oct 13 - Oct 14
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 $624 per night
CA $624
CA $749 total
Nov 2 - Nov 3
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 Middle Covered Bridge and Woodstock Town Hall Theatre are located nearby.
Pool
Hot tub
The Jackson

The Jackson

4 out of 5
43 Senior Lane Woodstock VT
38.99 km from city centre
The price is CA $273 per night
CA $273
CA $300 total
Nov 2 - Nov 3
includes taxes & fees
Stay at this B&B in Woodstock. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast in our reviews. Popular attractions Union Arena Community Center and Five Elm Arches are located nearby.
Parking included
Free WiFi
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 $213 per night
CA $213
CA $255 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 $118 per night
CA $118
CA $130 total
Nov 1 - Nov 2
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
Aspen At Manchester

Aspen At Manchester

2.5 out of 5
5669 Main Street Manchester Center VT
Free cancellation
Reserve now, pay when you stay
37.62 km from city centre
The price is CA $147 per night
CA $147
CA $177 total
Nov 2 - Nov 3
includes taxes & fees
Stay at this hotel in Manchester Center. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Bromley Mountain Ski Resort and Dana L. Thompson Memorial Park are located nearby.
Pool
Pet-friendly
The Manchester View

The Manchester View

2.5 out of 5
77 High Meadow Way & VT-7A Manchester Center VT
Free cancellation
Reserve now, pay when you stay
36.17 km from city centre
The price is CA $134 per night
CA $134
CA $148 total
Nov 2 - Nov 3
includes taxes & fees
Book a stay at this business-friendly 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 Bromley Mountain Ski Resort and Dana L. Thompson Memorial Park are located nearby.
Pool
Breakfast included
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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! (23 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
3,115 hotels
Lowest Price
CA $130
Highest Price
CA $749
Popular hotels
Fullerton Inn, Stone Hearth Inn and Eatery, Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area, Woodstock Inn & Resort, The Jackson , Grand Summit Resort, A Vail Resorts Property, Colonial Motel, Aspen At Manchester, The Manchester View

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 $130 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 3,115 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

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

5 out of 5
Posted 3 hours ago
Travelocity Verified Review
"Very nice place, quiet and easily accessible. Room was large with separate large bedroom with door. Large LR with fireplace, sofa & recliner and fully stocked kitchen."
A verified traveller stayed at Pointe at Castle Hill Resort
Pointe at Castle Hill Resort