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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
$499 nightly
The price is $549 total per night from Aug 10 to Aug 11
$549 total
Aug 10 - Aug 11
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 ...
"Service and concierge were excellent. Property was kept in a beautiful condition. Lost of inspiring rooms."

Reviewed on Jul 13, 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
$210 nightly
The price is $231 total per night from Jul 20 to Jul 21
$231 total
Jul 20 - Jul 21
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 ...
"Absolutely Beautiful property."

Reviewed on Jun 9, 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
$164 nightly
The price is $180 total per night from Jul 30 to Jul 31
$180 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.
"This is a lovely property in the town of Woodstock. We enjoyed our time there (and all the space in our room!). I left something in our room and did not realize it until the next day. I called the property to ask if anything had been found. They soon got back to me that they had my item and would ..."

Reviewed on Jul 10, 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
$120 nightly
The price is $133 total per night from Jul 15 to Jul 16
$133 total
Jul 15 - Jul 16
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 ...
"Amazing building with very knowledgeable and keen staff. Bustling city Centre but delivers comfort & an experience."

Reviewed on Jul 4, 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 15 to Jul 16
$173 total
Jul 15 - Jul 16
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 ...
"If you select The Fullerton for a comfy and cozy stay, do yourself a favor and have dinner there. The staff, specifically Hannah, are friendly, helpful and knowledgeable. The food and drinks are amazing with many vegetarian options. Save room for dessert! I had the creme brulee and it was sublime. ..."

Reviewed on Jul 3, 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 Jul 20 to Jul 21
$139 total
Jul 20 - Jul 21
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 ...
"Great hotel, friendly staff and very comfortable."

Reviewed on Jul 11, 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
$215 nightly
The price is $236 total per night from Jul 22 to Jul 23
$236 total
Jul 22 - Jul 23
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 ...
"Just love the very historic sence"

Reviewed on Jul 6, 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 15 to Jul 16
$120 total
Jul 15 - Jul 16
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. ...
"This is my go to place to stay. Its always clean, check in is quick and easy. The staff has always been polite and helpful when something has come up. The price is the best around."

Reviewed on Jul 8, 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 2,984 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 2 days ago
Travelocity Verified Review
"Just a wonderful place . Staff was so nice . The restaurant is delicious! Bartender makes great cocktails ! "
A verified traveler stayed at On The River Inn
On The River Inn
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