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Top Chester hotels

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
$359 nightly
The price is $395 total per night from May 25 to May 26
$395 total
May 25 - May 26
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 ...
Wonderful historic property with warm and thoughtful staff. Even though some areas in the lobby were being refurbished, we still enjoyed the experience. Look forward to returning when the huge fireplace in the lobby is back up and operational.

Reviewed on Apr 10, 2026

Opens in a new windowWoodstock Inn & Resort
On The River Inn

On The River Inn

4 out of 5
1653 West Woodstock Road Woodstock VT
$185 nightly
The price is $204 total per night from May 20 to May 21
$204 total
May 20 - May 21
Total with taxes and fees
This hotel features an indoor pool, a hot tub, and a restaurant. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the ...
I was at the inn for one night only, and I really enjoyed it. It's very clean and pleasant. My room was spacious, comfortable, and had a lovely view toward the river. The fire pit under a starry night was magical. The only part of the experience that left to be desired was the breakfast. It was ...

Reviewed on Apr 28, 2026

Opens in a new windowOn The River Inn
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
2940 State Route 103 Cavendish VT
$137 nightly
The price is $149 total per night from May 6 to May 7
$149 total
May 6 - May 7
Total with taxes and fees
A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center ...
Super kind staff members. Our family arrived early, and they were able to find a room for us within an hour. Pool is clean as well!

Reviewed on Apr 15, 2026

Opens in a new windowPointe at Castle Hill Resort
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St. Woodstock VT
Fully refundableReserve now, pay when you stay
$140 nightly
The price is $154 total per night from May 25 to May 26
$154 total
May 25 - May 26
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.
Nice hotel, they have fire pits outside which are a nice touch. Hot water for the showers was hit and miss, I think if you happen to shower at the same time/ after other guests then you miss out on the hot water which is disappointing. But otherwise great hotel

Reviewed on Apr 27, 2026

Opens in a new windowThe Shire Woodstock
Fullerton Inn

Fullerton Inn

2.5 out of 5
40 The Common Chester VT
Fully refundableReserve now, pay when you stay
$129 nightly
The price is $141 total per night from May 5 to May 6
$141 total
May 5 - May 6
Total with 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 ...
The staff were incredible and the property have the perfect vibes for a ski trip. The food was great and everything was very clean and comfy.

Reviewed on Apr 16, 2026

Opens in a new windowFullerton Inn
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road Brattleboro VT
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $143 total per night from May 6 to May 7
$143 total
May 6 - May 7
Total with 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 ...
We were well taken care of the whole time. Just a great all around experience

Reviewed on Apr 28, 2026

Opens in a new windowHampton 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
$154 nightly
The price is $170 total per night from May 10 to May 11
$170 total
May 10 - May 11
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 ...
The resort is nestled within a beautiful setting of mountains and the great town of Manchester With the best bookshop ever ! The equinox is a grand old building and I can only speak to my double queen room in the main hotel. Although clean I think the resort could do with an uplift of paint and window ...

Reviewed on Apr 29, 2026

Opens in a new windowThe Equinox Golf Resort & Spa
Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd Brattleboro VT
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. ...
Awesome and clean and quiet love the staff

Reviewed on Apr 14, 2026

Get rates
Opens in a new windowColonial Motel And Spa
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4 out of 5
3835 Main St. Manchester VT
Fully refundable
$196 nightly
The price is $216 total per night from May 25 to May 26
$216 total
May 25 - May 26
Total with 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 ...
Opens in a new windowKimpton Taconic Hotel by IHG
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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
8.4/10 Very Good! (71 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 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 $141. 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 3,126 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 Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4 out of 5
Posted 1 day ago
Travelocity Verified Review
"The resort is nestled within a beautiful setting of mountains and the great town of Manchester With the best bookshop ever ! The equinox is a grand old building and I can only speak to my double queen room in the main hotel. Although clean I think the resort could do with an uplift of paint and window replacement. The front desk was friendly but not informative . The pool could stay open later than 8 pm. And the restaurants are really expensive so perhaps dine in the town. The golf course is kept really well. And the staff were very helpful "
A verified traveler stayed at The Equinox Golf Resort & Spa
The Equinox Golf Resort & Spa

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