Find hotels in Chester, VT from $99

Check Chester hotel prices

Tomorrow night
Next weekend

Filter by

Popular filters
Popular filters
Guest rating
Guest rating
Star rating
Payment type
Payment type
Property type
Property type
Neighborhood
Neighborhood
Popular locations
Popular locations
Meal plans available
Meal plans available
Amenities
Amenities
Accessibility
Accessibility
Traveler experience
Traveler experience

Compare 2,916 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

The Putney Inn
2.5 star property
8.2 out of 10, Very Good, (913)
"Though there were some simple things that needed attention in the room, it was overall clean and presentable. I would certainly stay there again."
The price is $114
$125 total
includes taxes & fees
Jun 9 - Jun 10
The Putney Inn
Best Western Springfield Hotel
2.5 star property
8.8 out of 10, Excellent, (685)
"Food options fairly close, fuel options very close, the room was clean but had a hole in the carpet which was very evident. "
The price is $179
$195 total
includes taxes & fees
Jun 16 - Jun 17
Best Western Springfield Hotel
Windham Hill Resort
3.0 star property
8.2 out of 10, Very Good, (27)
"We stayed in the 8-room converted barn. The room very large and a pleasant surprise featuring a great view, soaking tub in the living area, gas fireplace, and a very comfortable king bed. I would give Windham Hill Inn five stars, but I deducted a star because of a clogged bathroom sink, a difficult to control HVAC system, and live and dead bugs in the room. Although somewhat dated, the room was spectacular for the price. "
The price is $173
$188 total
includes taxes & fees
Jun 9 - Jun 10
Windham Hill Resort
Save an average of 15% on thousands of hotels when you're signed in
Fullerton Inn
2.5 star property
8.2 out of 10, Very Good, (278)
"Bed and breakfast, room was small and no TV. Lot of antiques in every way so it was relaxing and unique experience."
The price is $139
$152 total
includes taxes & fees
Jun 9 - Jun 10
Fullerton Inn
Fairfield Inn & Suites by Marriott Keene Downtown
2.5 star property
8.8 out of 10, Excellent, (633)
"Nice hotel in prime downtown location. There is a parking garage (free)- you cannot park on the street overnight. Entire hotel smelled amazing, fresh and clean. "
The price is $110
$119 total
includes taxes & fees
Jun 30 - Jul 1
Fairfield Inn & Suites by Marriott Keene Downtown
Stone Hearth Inn and Eatery
2.0 star property
9.2 out of 10, Wonderful, (50)
"My fiance and I had an amazing stay here. Vicki and her staff are incredible and attentive to their guests. The food is beyond amazing one of the best meals we have had. We highly recommend this cute and quaint spot and definitely will be making many trips back! "
The price is $218
$238 total
includes taxes & fees
Jun 16 - Jun 17
Stone Hearth Inn and Eatery
The Hartness House
3.0 star property
8.0 out of 10, Very Good, (281)
"Really wonderful place- so comfortable, quiet and peaceful. Bar and bartender were also great- not a thing negative"
The price is $183
$200 total
includes taxes & fees
Jul 1 - Jul 2
The Hartness House
The Lodge at West River
2.5 star property
9.6 out of 10, Exceptional, (165)
"We stayed to see the eclipse the next day in Peacham VT. We wanted to be away from the crowds. We had cinnamon raisin toast and oatmeal for a quick breakfast. The room was clean and and fresh smelling as a non-smoking room. The bathroom was clean , the beds were comfortable, the hotel was quite and peaceful at night. TV was great with our Netflix account. The front desk staff was very courteous and polite and helpful with info about nearby events and services. All said it was a great stay."
The price is $135
$148 total
includes taxes & fees
Jun 15 - Jun 16
The Lodge at West River
Rodeway Inn
2.0 star property
6.2 out of 10, (242)
"Clean comfortable room."
The price is $99
$108 total
includes taxes & fees
Jun 9 - Jun 10
Rodeway Inn
The Burrell House
2.5 star property
9.6 out of 10, Exceptional, (90)
"Very clean and well maintained property. Easy check in and out process. Owners were very responsive."
The price is $161
$175 total
includes taxes & fees
Jun 11 - Jun 12
The Burrell House
Harvest Barn Inn
3.0 star property
9.6 out of 10, Exceptional, (171)
"I had a wonderful stay. Kaelan was an awesome host. great breakfast as well!"
The price is $170
$186 total
includes taxes & fees
Jun 12 - Jun 13
Harvest Barn Inn
Zen of the Woods Tiny Cabin in Okemo Valley
10.0 out of 10, Exceptional, (6)
"Nice small one-room cabin in the woods. The road is dirt and could have been difficult to traverse in snowy weather without 4-wheel drive, but was fine when we visited."
The price is $167
$338 total
includes taxes & fees
Jul 2 - Jul 3
Zen of the Woods Tiny Cabin in Okemo Valley
Family Friendly Hilltop House In Putney Vermont
9.6 out of 10, Exceptional, (50)
"The house was excellent and the view of the pond was amazing! But what we appreciated the most was Michele's help and communication about the snowstorm that was set to hit the area. She had excellent info and advice and was able to move our stay up a day so we could stay ahead of the storm. We had a great trip to Vermont and very much appreciate her help!"
The price is $216
$361 total
includes taxes & fees
Jun 11 - Jun 12
Family Friendly Hilltop House In Putney Vermont
King & Queen Suite in Historic Inn Circa 1780
9.6 out of 10, Exceptional, (13)
"SUCH a lovely, cozy stay in this beautiful VT town. Could not recommend more highly!"
The price is $279
$393 total
includes taxes & fees
Jun 9 - Jun 10
King & Queen Suite in Historic Inn Circa 1780
Cozy Camp in the woods surrounded by nature.!
10.0 out of 10, Exceptional, (10)
"Beautiful setting, quiet, bucolic. Cabin super clean and rustic. Well equipped, clean gym. Owners are super and very kind. A "
The price is $140
$204 total
includes taxes & fees
Jun 11 - Jun 12
Cozy Camp in the woods surrounded by nature.!
Grafton Inn
3.5 star property
9.6 out of 10, Exceptional, (80)
"Wonderful in every way."
The price is $249
$303 total
includes taxes & fees
Jun 13 - Jun 14
Grafton Inn
Chesterfield Inn
4.0 star property
9.0 out of 10, Wonderful, (101)
"A true find!"
The price is $301
$327 total
includes taxes & fees
Jun 9 - Jun 10
Chesterfield Inn
Log Cabin - Cozy, Quaint & Scenic and Ready for Your Enjoyment!
9.8 out of 10, Exceptional, (70)
"It was a nice cabin- perfect for getting away for a few days and nice place to stay for access to skiing"
Log Cabin - Cozy, Quaint & Scenic and Ready for Your Enjoyment!
Honeymoon Suite with Jacuzzi Tub in Historic Inn
8.0 out of 10, Very Good, (5)
"We had a fantastic time staying in the Chester House. It was a short drive to Okemo Mountain, which was our main reason for booking, but the town of Chester, like the room we stayed in, was incredibly charming!"
The price is $239
$334 total
includes taxes & fees
Jun 9 - Jun 10
Honeymoon Suite with Jacuzzi Tub in Historic Inn
Mountain Top Escape
9.0 out of 10, Wonderful, (7)
"Loved our stay. Great place to be rained in! :p"
Mountain Top Escape
Don't see what you're looking for?
See all available properties in Chester
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.

Stay near popular Chester attractions

Chester Travel Info

Number of reviews
3,791
Accommodation
2,916 hotels
Highest price
$301
Lowest price
$99
Why to go
DaVallia Art & Accents
Hotels with dining
12
Hotels with skiing
15

Frequently asked questions

Where is the best place to stay in Chester?

Stone Hearth Inn and Eatery is ranked highly by Expedia customers. This B&B offers free breakfast and free parking. Another top choice for your visit based on reviews is Fullerton Inn. See all available top hotels, or vacation rentals in Chester.

What's the top vacation rental that Chester has to offer?

Lakefront house with skiing nearby, dock, and amazing views - dog-friendly: You might want to consider this vacation home rental near Chester, which is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of books. See all vacation rentals in Chester.

If I need to cancel my hotel reservation in Chester, will I receive a refund?

Yes, the majority of hotel reservations are fully refundable provided that you cancel before the accommodation's cancellation deadline, which is often 24 or 48 hours before the scheduled arrival. If you have a non-refundable reservation, it might still be possible to cancel it and be given a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Chester.

Where can I learn more about changing or cancelling my trip to Chester?

For additional details about rescheduling or cancelling your trip to Chester, head over to our customer service page.

What's the best place to stay on a budget in Chester?

Based on reviews, The Karass Inn is a popular B&B for our travelers who want a more economical choice, and features free full breakfast and free WiFi. Another top choice for your stay on the cheap is Motel in the Meadow. View all budget hotels in Chester.

What's the best hotel for a family vacation to Chester?

1868 CARRIAGE HOUSE-QUAINT + COZY -PERFECT ESCAPE-20 MIN TO OKEMO! is a guesthouse with in-room kitchens and free WiFi, and it's a top choice on Expedia for families. Attractions like DaVallia Art & Accents and Bonnie's Bundles Dolls are also fun for kids of all ages. Find more child-friendly accommodations in Chester.

What's the best accommodation for a romantic vacation in Chester?

1868 CARRIAGE HOUSE-QUAINT + COZY -PERFECT ESCAPE-20 MIN TO OKEMO! is a favorite guesthouse for couples, and features free WiFi and a fitness center. See all romantic hotels in Chester.

What's the best pet-friendly accommodation in Chester?
Where is the best place to stay close to DaVallia Art & Accents?

Adjacent to DaVallia Art & Accents, Fullerton Inn is one of the top choices for your stay based on our traveler data, and this inn offers free breakfast and a restaurant. Other good options within a short distance include Hugging Bear Inn and Shoppe and Chester House Inn.

What about the best place to stay near Bonnie's Bundles Dolls?

One of the top choices for your stay is Fullerton Inn, located a short 0.5 mi (0.9 km) from Bonnie's Bundles Dolls, and this inn offers free breakfast and a restaurant. Hugging Bear Inn and Shoppe and Chester House Inn are two other good choices in the immediate area.

What's the best luxury place to stay in Chester?

Inn Victoria is a 4-star B&B with a winery and a deli, and it's a popular choice for Expedia travelers looking for a pampering stay. Find more luxury hotels in Chester.

What's the best place to stay for a winter vacation in Chester?

1868 CARRIAGE HOUSE-QUAINT + COZY -PERFECT ESCAPE-20 MIN TO OKEMO! is a top guesthouse for hitting the ski slopes, and features free WiFi and a fitness center. This guesthouse is located 22 minutes by car from Magic Mountain Ski Resort. Motel in the Meadow is another good option for your winter getaway. See all ski hotels in Chester.

Recent reviews of Chester hotels
Expedia verified reviews