Book Hotels in Chester, VT

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Top Chester hotels

Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

2.5 out of 5
4519 Main St, Manchester Center, VT
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $149 total per night from Oct 26 to Oct 27
$149 total
Oct 26 - Oct 27
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the hot tub and ...
"This was one of the best hotel experiences in this range I’ve ever had. Clean, well thought out, and comfortable room and building. Staff were all consistently engaged and friendly."

Reviewed on Sep 25, 2025

Opens in a new windowHampton Inn and Suites Manchester
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
$579 nightly
The price is $637 total per night from Oct 26 to Oct 27
$637 total
Oct 26 - Oct 27
Total with 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 ...
"Clean room. Staff very polite and helpful"

Reviewed on Sep 24, 2025

Opens in a new windowWoodstock Inn & Resort
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St., Woodstock, VT
Fully refundableReserve now, pay when you stay
$236 nightly
The price is $260 total per night from Oct 29 to Oct 30
$260 total
Oct 29 - Oct 30
Total with 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 little motel. Clean, well appointed, friendly staff and walkable location. We did not have good weather, but great fire pits and chairs near river."

Reviewed on Sep 25, 2025

Opens in a new windowThe Shire Woodstock
Jackson Gore Village

Jackson Gore Village

3 out of 5
111 Jackson Gore Road, Ludlow, VT
Fully refundableReserve now, pay when you stay
$193 nightly
The price is $213 total per night from Oct 27 to Oct 28
$213 total
Oct 27 - Oct 28
Total with taxes and fees
This smoke-free hotel features ski-in/ski-out access, a full-service spa, and 2 restaurants. There's a free ski shuttle, and ski lessons, ski passes and ski ...
"The property was beautiful and well-maintained, and the staff were helpful and friendly. I had a great stay and will definitely be returning in the future."

Reviewed on Sep 22, 2025

Opens in a new windowJackson Gore Village
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

2.5 out of 5
175 Key Rd, Keene, NH
Fully refundableReserve now, pay when you stay
$125 nightly
The price is $136 total per night from Oct 5 to Oct 6
$136 total
Oct 5 - Oct 6
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate ...
"Wonderful stay very nice place comfortable bed."

Reviewed on Sep 18, 2025

Opens in a new windowKeene Elm City Hotel, an Ascend Collection Hotel
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

3 out of 5
401 Winchester St, Keene, NH
Fully refundableReserve now, pay when you stay
$149 nightly
The price is $162 total per night from Sep 29 to Sep 30
$162 total
Sep 29 - Sep 30
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. ...
Nice stay and great pool amenities!
"Overall it was a nice stay for a family event. The room was clean and had no issues. The pool was great and well heated!"

Reviewed on Sep 21, 2025

Opens in a new windowBest Western Plus Keene Hotel
The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
1043 Putney Road, Brattleboro, VT
Fully refundableReserve now, pay when you stay
$88 nightly
The price is $97 total per night from Sep 29 to Sep 30
$97 total
Sep 29 - Sep 30
Total with taxes and fees
This hotel features free self parking and free WiFi in public areas. Enjoy the free continental breakfast each morning.
"This hotel met our needs for an overnight stay. Our one criticism: The bathroom sink should drain faster."

Reviewed on Sep 10, 2025

Opens in a new windowThe Covered Bridge Inn
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
$171 nightly
The price is $189 total per night from Oct 27 to Oct 28
$189 total
Oct 27 - Oct 28
Total with 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 ...
"Such a beautiful location! Especially love the fire pit outside of the Falcon Bar"

Reviewed on Sep 24, 2025

Opens in a new windowThe Equinox Golf Resort & Spa
Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

2 out of 5
3 Ash Brook Road, Keene, NH
Fully refundableReserve now, pay when you stay
$97 nightly
The price is $105 total per night from Sep 30 to Oct 1
$105 total
Sep 30 - Oct 1
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Business travelers can take advantage of the ...
"Over all I was pleased with the handicapped room here."

Reviewed on Sep 7, 2025

Opens in a new windowDays Inn by Wyndham Keene NH
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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 $97. 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 2,964 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.

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