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Check Chester hotel prices

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Jun 1 - Jun 2
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Jun 2 - Jun 3
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Jun 7 - Jun 9

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Compare 2,915 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

The Putney Inn
Exterior
The Putney Inn
2.5 star property
8.2 out of 10, Very Good, (909)
"Easy, quick check in, friendly staff. Some noise from neighbors to be expected. Very clean, good sleep, pleasant stay. Would return. "
The price is $142
$155 total
includes taxes & fees
Jun 3 - Jun 4
The Putney Inn
Best Western Springfield Hotel
Lobby
Best Western Springfield Hotel
2.5 star property
8.8 out of 10, Excellent, (684)
"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
Exterior
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 2 - Jun 3
Windham Hill Resort
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Fullerton Inn
Standard Room, 2 Double Beds | Iron/ironing board, free WiFi, bed sheets
Fullerton Inn
2.5 star property
8.2 out of 10, Very Good, (277)
"Very interesting place. I loved the historic feel. However, the floors were very squeaky and almost felt like you could fall through sometimes. The continental breakfast, although appreciated, was very slim. One type of (huge) muffins, stale bagels, yogurt, orange juice, coffee. Having some milk, cereal or fruit would have been nice. Friendly staff however, we barely saw anyone at all."
The price is $139
$152 total
includes taxes & fees
Jun 3 - Jun 4
Fullerton Inn
Fairfield Inn & Suites by Marriott Keene Downtown
Exterior
Fairfield Inn & Suites by Marriott Keene Downtown
2.5 star property
8.8 out of 10, Excellent, (632)
"Perfect location in downtown Keene. Kind staff and clean rooms. Free coffee in lobby and attached to a great restaurant. "
The price is $127
$138 total
includes taxes & fees
Jul 1 - Jul 2
Fairfield Inn & Suites by Marriott Keene Downtown
Stone Hearth Inn and Eatery
Front of property
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 $233
$254 total
includes taxes & fees
Jun 2 - Jun 3
Stone Hearth Inn and Eatery
The Hartness House
Interior
The Hartness House
3.0 star property
8.0 out of 10, Very Good, (280)
"I loved the historic feel."
The price is $185
$201 total
includes taxes & fees
Jul 1 - Jul 2
The Hartness House
The Lodge at West River
Lobby lounge
The Lodge at West River
2.5 star property
9.6 out of 10, Exceptional, (165)
"I never usually stay at a motel but this was the more affordable option given the proximity to all the name brand mountains. I was pleasantly surprised at the cleanliness and the welcoming nature of the office and shared space (first and 2nd floor). The 2nd floor is where they serve a nice breakfast spread, with tv, books and games and some tables -- a nice second option for when you dont want to be in the motel room, or when you get take out dinner and want some tables. It snowed overnight and...
The price is $127
$139 total
includes taxes & fees
Jun 30 - Jul 1
The Lodge at West River
Rodeway Inn
Lobby
Rodeway Inn
2.0 star property
6.2 out of 10, (241)
"Clean comfortable room."
The price is $99
$108 total
includes taxes & fees
Jun 2 - Jun 3
Rodeway Inn
The Burrell House
Exterior
The Burrell House
2.5 star property
9.6 out of 10, Exceptional, (89)
"Very clean and well maintained property. Easy check in and out process. Owners were very responsive."
The price is $149
$161 total
includes taxes & fees
Jun 2 - Jun 3
The Burrell House
Harvest Barn Inn
Porch
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
Exterior
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
Exterior
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 $195
$335 total
includes taxes & fees
Jun 27 - Jun 28
Family Friendly Hilltop House In Putney Vermont
King & Queen Suite in Historic Inn Circa 1780
Interior
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 3 - Jun 4
King & Queen Suite in Historic Inn Circa 1780
Cozy Camp in the woods surrounded by nature.!
Fridge, microwave, oven, stovetop
Cozy Camp in the woods surrounded by nature.!
10.0 out of 10, Exceptional, (10)
"We booked the cabin in the woods for family ski/snowboard trip. Crotched mountain was perfect for the kids learning and for us to enjoy as well. The mountain was about 45 minute drive from the cabin. We also were able to skate on the lake which it's a few minutes walk from the cabin. We really enjoyed exploring the farm and meeting the animals. I asked ahead of our stay what they would have available to purchase from the farm and Jenny stocked our fridge with delicious pasture raised meats....
The price is $140
$204 total
includes taxes & fees
Jun 3 - Jun 4
Cozy Camp in the woods surrounded by nature.!
Grafton Inn
Reception
Grafton Inn
3.5 star property
9.6 out of 10, Exceptional, (80)
"Wonderful in every way."
The price is $224
$276 total
includes taxes & fees
Jun 13 - Jun 14
Grafton Inn
Chesterfield Inn
Lobby
Chesterfield Inn
4.0 star property
9.0 out of 10, Wonderful, (100)
"A true find!"
The price is $301
$327 total
includes taxes & fees
Jun 6 - Jun 7
Chesterfield Inn
Log Cabin - Cozy, Quaint & Scenic and Ready for Your Enjoyment!
Dining
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
1 bedroom, desk, iron/ironing board, free WiFi
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 2 - Jun 3
Honeymoon Suite with Jacuzzi Tub in Historic Inn
Mountain Top Escape
Property grounds
Mountain Top Escape
9.0 out of 10, Wonderful, (7)
"Loved our stay. Great place to be rained in! :p"
Mountain Top Escape
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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.

More cheap stays in Chester

The Covered Bridge Inn

The Covered Bridge Inn

1043 Putney Road, Brattleboro, VT
The price is $85 per night from Jun 3 to Jun 4
$85
$95 total
includes taxes & fees
Jun 3 - Jun 4
8.2/10 Very Good! (1,001 reviews)

Stay near popular Chester attractions

Image for Bonnie's Bundles Dolls

Bonnie's Bundles Dolls

Enjoy an outing to Bonnie's Bundles Dolls during your stay in Chester. Discover the area's mountain views, or seek out its ski slopes.

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Bonnie's Bundles Dolls
Image for DaVallia Art & Accents

DaVallia Art & Accents

Enjoy an outing to DaVallia Art & Accents during your stay in Chester. You can seek out the ski slopes while in the area.

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DaVallia Art & Accents

Chester Travel Info

Number of reviews
4,101
Accommodation
2,915 hotels
Highest price
$301
Lowest price
$85
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?

Stunning farmhouse in gorgeous historic village is a top pet-friendly option for your stay. Other good choices for you and your pet include Farmhouse w/ mountain views close to skiing. Includes outdoor sauna EV CHRGR and Motel in the Meadow. See more pet-friendly hotel accommodations 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

Colonial Motel And Spa

Colonial Motel And Spa

5/5 Excellent
"I got the 1 bedroom suite there. It was very spacious and comfortable. The perfect place if you want to sleep well. The bedding was ultra comfortable and I had everything I needed."
A verified traveler stayed at Colonial Motel And Spa
Posted 2 days ago
Colonial Motel And Spa