Book Cheap Hotels in Chester

Start date: Check-in selected.
To Date
End date: Check-out

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Check hotel availability in Chester

Tonight
Check prices in Chester for tonight, Nov 23 - Nov 24
Nov 23 - Nov 24
Tomorrow night
Check prices in Chester for tomorrow night, Nov 24 - Nov 25
Nov 24 - Nov 25
Next weekend
Check prices in Chester for next weekend, Nov 28 - Nov 30
Nov 28 - Nov 30

Most frequently booked Chester hotels

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 $464 per night
CA $464
CA $572 total
Nov 30 - Dec 1
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 Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St. Woodstock VT
Free cancellation
Reserve now, pay when you stay
41.03 km from city centre
The price is CA $151 per night
CA $151
CA $176 total
Nov 30 - Dec 1
includes taxes & fees
Stay at this hotel in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Billings Park and Trail and Red Wagon Toy Company are located nearby.
Pet-friendly
Parking included
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4 out of 5
3835 Main St. Manchester VT
Free cancellation
40.02 km from city centre
The price is CA $224 per night
CA $224
CA $301 total
Dec 1 - Dec 2
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
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
3567 Main Street Route 7A Manchester VT
Free cancellation
Reserve now, pay when you stay
40.25 km from city centre
The price is CA $191 per night
CA $191
CA $286 total
Dec 10 - Dec 11
includes taxes & fees
Book a stay at this luxury hotel in Manchester. Enjoy free parking, an outdoor pool, and a full-service spa. Popular attractions Golf Club at Equinox and American Museum of Fly Fishing are located nearby.
Pool
Hot tub
Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

2.5 out of 5
4519 Main St Manchester Center VT
Free cancellation
Reserve now, pay when you stay
39.11 km from city centre
The price is CA $179 per night
CA $179
CA $197 total
Dec 14 - Dec 15
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 breakfast and the helpful staff in our reviews. Popular attractions Manchester Designer Outlets and American Museum of Fly Fishing 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
Get rates
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
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road Brattleboro VT
Free cancellation
Reserve now, pay when you stay
41.48 km from city centre
The price is CA $202 per night
CA $202
CA $222 total
Nov 30 - Dec 1
includes taxes & fees
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions United States Navy Seabee Bridge and Brattleboro Bowl are located nearby.
Pool
Hot tub
On The River Inn

On The River Inn

4 out of 5
1653 West Woodstock Road Woodstock VT
38.74 km from city centre
The price is CA $272 per night
CA $272
CA $351 total
Dec 2 - Dec 3
includes taxes & fees
Book a stay at this family-friendly hotel in Woodstock. Enjoy free WiFi, free parking, and a fitness center. 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
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
2940 State Route 103 Cavendish VT
14.11 km from city centre
The price is CA $193 per night
CA $193
CA $221 total
Nov 24 - Nov 25
includes taxes & fees
Book a stay at this spa hotel in Cavendish. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Okemo Mountain Resort and Phineas Gage Memorial are located nearby.
Pool
Hot tub
Don't see what you're looking for?
See all available properties in Chester
View all properties
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

Top hotels in Chester for Extended Stay

Ski-In Resort Room | 2 Queen Beds

Ski-In Resort Room | 2 Queen Beds

West Dover VT
The price is CA $255 per night from Nov 24 to Nov 25
CA $255
CA $324 total
Nov 24 - Nov 25
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
3,027 hotels
Lowest Price
CA $176
Highest Price
CA $587
Popular hotels
Woodstock Inn & Resort, The Shire Woodstock, Kimpton Taconic Hotel by IHG, The Equinox Golf Resort & Spa, Hampton Inn and Suites Manchester, The Jackson , Hampton Inn Brattleboro, On The River Inn, Pointe at Castle Hill Resort

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 $176 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 3,027 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

Hampton Inn Brattleboro

Hampton Inn Brattleboro

5 out of 5
Posted 3 days ago
Travelocity Verified Review
"Everything was very nice. I was checked in at the desk by "Jolene" who was cordial, friendly, and welcoming. The room was very clean and it was very quiet. The breakfast in the morning was excellent as was the coffee station. I do miss the little snack bag at the front desk where we could grab 'n go off for the day. All was very nice. Thank you!"
A verified traveller stayed at Hampton Inn Brattleboro
Hampton Inn Brattleboro

Hotels near…

Areas of Chester