Find hotels in Chester, VT from CA $105

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Top 10 Chester hotels and places to stay

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."
Zen of the Woods Tiny Cabin in Okemo Valley
Fridge, microwave, oven, stovetop
Cozy Camp in the woods surrounded by nature.!
10.0 out of 10, Exceptional, (9)
"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 CA $191
CA $280 total
includes taxes & fees
May 20 - May 21
Cozy Camp in the woods surrounded by nature.!
Interior
Whimsical Room & Private Bathroom in Historic Inn
10.0 out of 10, Exceptional, (3)
"We had a great stay. Everything we needed was there. Only issue was I couldn't do anything with VRBO on my cell. I signed in and found no links to the property information. AND, plenty of advertising to book another trip. Had to go to the local library to fire up my computer so that we could communicate with the host, Tyler. He was awesome and responded to all my communication promptly. We will be back."
The price is CA $273
CA $392 total
includes taxes & fees
May 15 - May 16
Whimsical Room & Private Bathroom in Historic Inn
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Exterior
Brand New Luxury “Tiny” House, Immersed In Nature
10.0 out of 10, Exceptional, (1)
"This is by far the most beautiful home I’ve ever stayed! So clean and amazing views of nature. We can’t wait to come back."
The price is CA $376
CA $593 total
includes taxes & fees
May 15 - May 16
Brand New Luxury “Tiny” House, Immersed In Nature
Exterior
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT
10.0 out of 10, Exceptional, (38)
"The house was very clean and cozy. Nice and peaceful get away in a remote cabin with my wife and both of the dogs! They provided dog toys and a bed for our pups with additional treats, they were very happy about this! If you are looking for a quiet get away to slow down and reconnect with your family this is the place to be!"
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT
Property grounds
NEW! Secluded Log Cabin in the Mountains -- Minutes from Okemo
10.0 out of 10, Exceptional, (12)
"Beautiful, well kept house with easy commute to major mountains "
NEW! Secluded Log Cabin in the Mountains -- Minutes from Okemo
Smart TV, DVD player, books
Sunny, convenient 4-Bed Family Base w/Balcony: Fast WiFi, WFH, 15 min to ski!
10.0 out of 10, Exceptional, (6)
"My family has loved staying here two years in a row for a ski weekend. Perfect distance to Mt Snow and Stratton. Great living room/kitchen setup to hang after a full day of skiing"
Sunny, convenient 4-Bed Family Base w/Balcony: Fast WiFi, WFH, 15 min to ski!
Fridge, microwave, oven, stovetop
Potter's Place | House in Jamaica with mountain views
10.0 out of 10, Exceptional, (2)
"The house was warm, clean, peaceful and comfortable for our short stay. We were in VT to ski at Stratton but I would love to come back in other seasons to explore the nearby state parks. I would gladly stay at this property again."
Potter's Place | House in Jamaica with mountain views
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!
Fridge, microwave, oven, stovetop
Open, Sunlit Cottage; hiking, fishing, kayaking, skiing. Water access!
9.8 out of 10, Exceptional, (13)
"We loved our stay at the Cozy Cabin! It was wonderful to view the sunrise over the lake from the windows each morning. The lake was easy to access. The owners of the cabin were very helpful and have thought of everything to make things comfortable and enjoyable. It’s a good idea to plan your meals and bring all of your food with you so you never have to leave and can enjoy all of your time at the cabin and on the lake. This was a perfect choice for our family to enjoy a fall weekend in New...
Open, Sunlit Cottage; hiking, fishing, kayaking, skiing. Water access!
Golf
Riverfront, family fun, amazing rec room, close to Magic & Okemo
9.8 out of 10, Exceptional, (7)
"Very comfortable and clean home. My friends and I came into town for a snowboarding trip, and the home was the perfect fit for us."
Riverfront, family fun, amazing rec room, close to Magic & Okemo
Lobby lounge
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 CA $203
CA $222 total
includes taxes & fees
Jun 12 - Jun 13
The Lodge at West River
Exterior
The Burrell House
2.5 star property
9.6 out of 10, Exceptional, (86)
"We will be back! Very nice place to stay!"
The price is CA $186
CA $202 total
includes taxes & fees
May 15 - May 16
The Burrell House
Porch
Harvest Barn Inn
3.0 star property
9.6 out of 10, Exceptional, (169)
"Excellent B&B! Very cozy and friendly, gourmet breakfasts. And the town is very cool and artsy, good coffee shops. "
The price is CA $233
CA $254 total
includes taxes & fees
May 26 - May 27
Harvest Barn Inn
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 CA $243
CA $428 total
includes taxes & fees
May 15 - May 16
Family Friendly Hilltop House In Putney Vermont
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 CA $163
CA $268 total
includes taxes & fees
May 15 - May 16
King & Queen Suite in Historic Inn Circa 1780
Reception
Grafton Inn
3.5 star property
9.6 out of 10, Exceptional, (80)
"Wonderful in every way."
The price is CA $306
CA $377 total
includes taxes & fees
Jun 4 - Jun 5
Grafton Inn
Outdoor pool
Windham Hill Inn
4.0 star property
9.2 out of 10, Wonderful, (47)
"This Inn was absolutely gorgeous. The room was so nice and cozy, I didn’t want to leave for dinner. I can’t wait to see it in the spring time."
Windham Hill Inn
Exterior
Fairfield Inn & Suites by Marriott Keene Downtown
2.5 star property
9.0 out of 10, Wonderful, (627)
"Downtown Keene "
The price is CA $180
CA $196 total
includes taxes & fees
Jun 2 - Jun 3
Fairfield Inn & Suites by Marriott Keene Downtown
Front of property
Stone Hearth Inn and Eatery
2.0 star property
9.0 out of 10, Wonderful, (48)
"Vicky and her family are wonderful hosts. We stayed on the last day of their season and received as welcoming a reception as you might expect at the height of the season. Stonehearth Inn is a labor of love and it shows. "
The price is CA $319
CA $347 total
includes taxes & fees
May 16 - May 17
Stone Hearth Inn and Eatery
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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.

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.

What are some accommodations with pools in Chester?

Colonial Motel And Spa: Features a full-service spa, 2 indoor pools, and a sauna. Woodstock Inn & Resort and Hampton Inn and Suites Manchester are two additional hotels with an onsite pool. View all hotels with pools in Chester.

What is the best spa hotel in Chester?

1868 CARRIAGE HOUSE-QUAINT + COZY -PERFECT ESCAPE-20 MIN TO OKEMO! is a top spa hotel featuring a pool and a fitness center. Why not spend some time relaxing in the spa tub? See all spa hotels in Chester.

What's the best accommodation near Hartness State Airport (VSF)?

The Inn at Weathersfield is a popular 4-star inn featuring free breakfast and a restaurant. It's located a short 1.3 mi (2.1 km) from Hartness State Airport. Another good choice close to the airport is Hartness House Inn, located 3.7 mi (5.9 km) away.

What is staying in Chester like?

Visitors to Chester are sure to enjoy the ski areas, coffeehouses, and shopping. Quaint and relaxing, this city also attracts tourists with its restaurants. In Chester, there are 70 hotels and other accommodations to choose from. Find out more about Chester.

What should I see while I'm in Chester?

A couple of favorite places to visit are DaVallia Art & Accents and Bonnie's Bundles Dolls. You'll also find Vermont Country Store and Baltimore Covered Bridge in the area. Check out what more to see and do in Expedia's Chester guide.

What's the weather like in Chester?

The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Chester are January, March, November, and February, with each month seeing an average of 14 inches of snowfall.