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May 13 - May 14
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May 14 - May 15
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May 17 - May 19
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Top hotels and accommodation in Chester

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 NZ$339
includes taxes & fees
15 May - 16 May
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 NZ$471
includes taxes & fees
15 May - 16 May
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 NZ$721
includes taxes & fees
14 May - 15 May
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!
Interior
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 NZ$268
includes taxes & fees
11 Jun - 12 Jun
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 NZ$246
includes taxes & fees
14 May - 15 May
The Burrell House
Porch
Harvest Barn Inn
3.0 star property
9.6 out of 10, Exceptional, (169)
"Friendly staff and good location."
The price is NZ$308
includes taxes & fees
26 May - 27 May
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 NZ$518
includes taxes & fees
15 May - 16 May
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 NZ$324
includes taxes & fees
14 May - 15 May
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 NZ$459
includes taxes & fees
4 Jun - 5 Jun
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 NZ$214
includes taxes & fees
9 Jun - 10 Jun
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 NZ$422
includes taxes & fees
14 May - 15 May
Stone Hearth Inn and Eatery
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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 accommodation in Chester

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

3 Ash Brook Road, Keene, NH
The price is NZ$159 per night from May 21 to May 22
NZ$159
per night
21 May - 22 May
7.2/10 Good! (872 reviews)

Stay near top 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.

See properties
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 hotels information

Number of reviews
4,504
Accommodation
2,944 hotels
Lowest Price
NZ$159
Highest Price
NZ$721

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 trip based on reviews is Fullerton Inn. See all available top hotels, or vacation rentals in Chester.

What are some of the best holiday rentals that Chester has to offer?

Lakefront house with skiing nearby, dock, and amazing views - dog-friendly: This holiday home rental outside of Chester is located on a lake, and has a fireplace, a patio and a BBQ 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 that 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 if cancelled prior to the hotel's cancellation deadline, which is often 24 or 48 hours before your check-in date. If your reservation is non-refundable, it may still be possible to cancel it and get a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Chester.

What's the best accommodation for a budget-friendly stay in Chester?

Based on reviews, The Karass Inn is a popular B&B for our travellers 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 family accommodation in 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. Also, attractions such as DaVallia Art & Accents and Bonnie's Bundles Dolls are fun for children of all ages. Find more child-friendly accommodations in Chester.

What's the best place to stay for a romantic holiday in Chester?

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

What's the best dog-friendly accommodation option in Chester?

Stunning farmhouse in gorgeous historic village is a top dog-friendly option for your stay. Other good choices for you and your pet's trip 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.

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 travellers looking for a pampered stay. Find more luxury hotels in Chester.

What's the best accommodation option for a trip to the slopes in Chester?

1868 CARRIAGE HOUSE-QUAINT + COZY -PERFECT ESCAPE-20 MIN TO OKEMO! is a top guest house for hitting the ski slopes, and features free WiFi and a fitness centreThis guest house 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 accommodation options with pools in Chester?

Colonial Motel And Spa: Features a full-service spa, 2 indoor swimming pools and a sauna. Woodstock Inn & Resort and Hampton Inn and Suites Manchester are two additional hotels that feature an on-site 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 centre. Why not spend some time relaxing in the hot tub? See all spa hotels in Chester.

What is staying in Chester like?

Visitors to Chester will definitely enjoy the skiing, cafes and shopping. Quaint and relaxing, this city also attracts tourists with its restaurants. In Chester, there are 70 hotels and other accommodation options to choose from. Find out more about Chester.

Recent Reviews in Chester
Expedia verified reviews

Colonial Motel And Spa

Colonial Motel And Spa

5/5 Excellent
" FAST FRINDLY SERVICE !!!!!!!!!!!! "
A verified traveller stayed at Colonial Motel And Spa
Posted 3 days ago
Colonial Motel And Spa
The Shire Woodstock

The Shire Woodstock

5/5 Excellent
"Outstanding "
A verified traveller stayed at The Shire Woodstock
Posted 11 days ago
The Shire Woodstock