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Top Chester hotels

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
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 ...
Hidden gem!
"This lovingly built off-grid glamping cabin is drenched with sun! It’s absolutely gorgeous! The kids enjoyed pumping their own water and sledding down the front hill. Paris is an excellent hostess- she answered all our questions very promptly & thoroughly. We cant wait to come back! Thank you!!!"

Reviewed on Feb 24, 2025

Get rates
Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
$489 nightly
The price is $538 total per night from Aug 17 to Aug 18
$538 total
Aug 17 - Aug 18
Total includes taxes and fees
This luxury resort features a golf course, a full-service spa, and 4 restaurants. Enjoy the 2 indoor tennis courts and perks like free valet parking and free ...
"Really enjoyed our stay."

Reviewed on Jul 18, 2025

Woodstock Inn & Resort
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4 out of 5
3835 Main St., Manchester, VT
Fully refundable
$238 nightly
The price is $262 total per night from Jul 30 to Jul 31
$262 total
Jul 30 - Jul 31
Total includes taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. If you want to take your pet along, this pet-friendly property offers everything you'll need ...
"I love that the hotel is dog friendly and have bikes and scooters available for guests. The room was comfortable and clean, nicely furnished. Staff was outstanding"

Reviewed on Jul 15, 2025

Kimpton Taconic Hotel by IHG
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St., Woodstock, VT
Fully refundableReserve now, pay when you stay
$178 nightly
The price is $196 total per night from Jul 30 to Jul 31
$196 total
Jul 30 - Jul 31
Total includes taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden and a picnic area are also provided.
"Great spot on the river!"

Reviewed on Jul 23, 2025

The Shire Woodstock
Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street, Brattleboro, VT
Fully refundableReserve now, pay when you stay
$134 nightly
The price is $148 total per night from Jul 28 to Jul 29
$148 total
Jul 28 - Jul 29
Total includes taxes and fees
A restaurant and a bar/lounge are featured at this hotel. Guests will appreciate free perks like free self parking and WiFi in public areas. Free parking and ...
Comfortable and central Location
"The room was ok. The a/c was too cold and was unable to control because the vent was too high up on the wall to reach. Cleaning the room had to be arranged at a certain period of time. Its location was central to Brattleboro right near the Brattleboro art museum and some restaurants. However a lot ..."

Reviewed on Jul 22, 2025

Latchis Hotel
Fullerton Inn

Fullerton Inn

2.5 out of 5
40 The Common, Chester, VT
Fully refundableReserve now, pay when you stay
$159 nightly
The price is $173 total per night from Jul 29 to Jul 30
$173 total
Jul 29 - Jul 30
Total includes taxes and fees
A restaurant and a bar/lounge are featured at this inn. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self ...
"No TV. No Elevator. Breakfast was lacking. Staff was wonderful and friendly. Rooms clean. Bathrooms are very tight but to be expected with the age of the inn. Loved the balcony off the room. We sat outside and played cards. Quiet area and restaurant downstairs."

Reviewed on Jul 14, 2025

Fullerton Inn
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road, Brattleboro, VT
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $139 total per night from Aug 17 to Aug 18
$139 total
Aug 17 - Aug 18
Total includes taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot ...
"The peoplw were nice The room was clean For the price upgrades are needed"

Reviewed on Jul 20, 2025

Hampton Inn Brattleboro
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
3567 Main Street Route 7A, Manchester, VT
Fully refundableReserve now, pay when you stay
$202 nightly
The price is $222 total per night from Aug 24 to Aug 25
$222 total
Aug 24 - Aug 25
Total includes taxes and fees
This luxury hotel features a golf course, a full-service spa, and 4 restaurants. Enjoy the 3 outdoor tennis courts and get free self parking. Make the most of ...
"The staff here is amazing. Super friendly. The hotel rooms were nice for an older building. Stay here for the history."

Reviewed on Jul 21, 2025

The Equinox Golf Resort & Spa
Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd, Brattleboro, VT
Fully refundableReserve now, pay when you stay
$109 nightly
The price is $120 total per night from Jul 27 to Jul 28
$120 total
Jul 27 - Jul 28
Total includes taxes and fees
This smoke-free motel features a full-service spa, 2 indoor pools, and a restaurant. Business travelers can take advantage of the free WiFi in public areas. ...
Very good last-minute stay
"I booked this room last-minute but checkin was smooth, room was comfortable. I like that there are two restaurants in walking distance."

Reviewed on Jul 14, 2025

Colonial Motel And Spa
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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.

Cheap Chester hotels

Motel in the Meadow

Motel in the Meadow

936 VT Route 11 West, Chester, VT
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 Hotel & Travel Guide\n

Are you intending on traveling in Central Vermont- Killington and looking to book lodgings around the Chester area? 7 hotels and apartments are within 6-mile (10-kilometer) of Chester and its surrounds.

Some of the more central Travelocity-listed hotels of downtown Chester are the Hugging Bear Inn and Shoppe and Fullerton Inn Bed & Breakfast.

Travelocity's extensive database offers only a limited number of economical hotel options in Chester. The Rose Arbour Bed & Breakfast is one of them.

The Castle Hill Resort And Spa is situated 9 miles (14 kilometers) outside of the main part of Chester. An alternative accommodation option is the Mountain Lodge at Okemo Mountain Resort, which is situated 12 miles (19 kilometers) away. Another possibility is to check out the rates and amenities at the Jackson Gore Inn or the The Andrie Rose Inn.

On your travels, why don't you check out some more of the forests and mountains that are commonly found in Central Vermont? Allow yourself to give yourself a few extra days in some other parts of Central Vermont. If you participate in common ways of enjoying yourself, such as snowboarding, skiing and cross-country skiing, or cross the region to see the landmarks, you'll be able to book the perfect Travelocity-registered lodgings in the local area.

Killington is 30 miles (45 kilometers) to the northwest of Chester and is home to Killington Ski Resort and Green Mountain National Golf Course. If you spend a few nights in Killington, be sure to check out the Killington Grand Resort Hotel and Mountain Green Ski & Golf Resort. Alternatively, you could stay in Rutland, 30 miles (49 kilometers) to the northwest of Chester, where you have the options of the Hampton Inn Rutland and Holiday Inn Rutland-Killington Area. The Pine Hill Park and Vermont State Fairgrounds are other frequented sites to visit should you visit Rutland.

Ensure a serving of sport by making a trek to Verizon Wireless Arena, which is 60 miles (97 kilometers) to the east of Chester. Travelers who like the thought of booking a room close to the stadium, book a room in the Hilton Garden Inn Manchester Downtown or Radisson Hotel Manchester Downtown.

After you have learnt a little about the Travelocity-listed accommodation options in Chester, take the time to browse our Chester travel page for local secrets on all the scenic and cultural attractions in this corner of the world.

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 $120. 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 2,985 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 Shire Woodstock

The Shire Woodstock

5 out of 5
Posted 1 day ago
Travelocity Verified Review
"Great spot on the river!"
A verified traveler stayed at The Shire Woodstock
The Shire Woodstock
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