Chester Hotels from S$134

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23 Aug - 24 Aug
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29 Aug - 31 Aug
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Top 10 trending Chester hotels

Fullerton Inn
Garden

Fullerton Inn

2.5 star property
8.2 out of 10, Very good, (371)
"Everything was Awsome friendly staff"
The price is S$195
includes taxes & fees
1 Sept - 2 Sept
Fullerton Inn
Stone Hearth Inn and Eatery
Front of property

Stone Hearth Inn and Eatery

3.0 star property
9.2 out of 10, Wonderful, (93)
"Sweet place to stay"
The price is S$281
includes taxes & fees
25 Aug - 26 Aug
Stone Hearth Inn and Eatery
Woodstock Inn & Resort
Lobby

Woodstock Inn & Resort

4.5 star property
9.2 out of 10, Wonderful, (532)
"Relaxing "
The price is S$633
includes taxes & fees
1 Sept - 2 Sept
Woodstock Inn & Resort
Aspen At Manchester
Meeting facility

Aspen At Manchester

2.5 star property
8.8 out of 10, Excellent, (580)
"Quiet, clean rooms very convenient to town center and the green mountain bluegrass festival. Would definitely stay here again. "
The price is S$178
includes taxes & fees
2 Sept - 3 Sept
Aspen At Manchester
The Shire Woodstock
Property grounds

The Shire Woodstock

3.0 star property
8.8 out of 10, Excellent, (809)
"Enjoyed our stay and will return"
The Shire Woodstock
The Covered Bridge Inn
Exterior detail

The Covered Bridge Inn

2.5 star property
7.8 out of 10, Good, (1001)
"Was great for the price "
The price is S$199
includes taxes & fees
20 Sept - 21 Sept
The Covered Bridge Inn
Hampton Inn and Suites Manchester
Front of property – evening/night

Hampton Inn and Suites Manchester

2.5 star property
9.6 out of 10, Exceptional, (1000)
"Great hotel"
The price is S$214
includes taxes & fees
7 Sept - 8 Sept
Hampton Inn and Suites Manchester
Sleep Woodstock Motel
2 bedrooms, individually decorated, desk, blackout curtains

Sleep Woodstock Motel

2.0 star property
9.6 out of 10, Exceptional, (512)
"Rooms are very clean , staff are very friendly , we enjoy our stay here . "
The price is S$167
includes taxes & fees
25 Aug - 26 Aug
Sleep Woodstock Motel
The Equinox Golf Resort & Spa
Exterior

The Equinox Golf Resort & Spa

4.5 star property
7.4 out of 10, Good, (515)
"The staff was friendly. "
The price is S$256
includes taxes & fees
1 Sept - 2 Sept
The Equinox Golf Resort & Spa
The Black Bear Lodge at Stratton Mountain Resort
Indoor spa tub

The Black Bear Lodge at Stratton Mountain Resort

3.0 star property
7.6 out of 10, Good, (911)
"Nice area"
The price is S$187
includes taxes & fees
8 Sept - 9 Sept
The Black Bear Lodge at Stratton Mountain Resort
The Palmer House Resort, Ascend Hotel Collection
Property amenity

The Palmer House Resort, Ascend Hotel Collection

3.0 star property
8.4 out of 10, Very good, (810)
"We had a great stay and the jacuzzi tub in our room was great. We will definitely be returning again."
The price is S$212
includes taxes & fees
25 Aug - 26 Aug
The Palmer House Resort, Ascend Hotel Collection
Best Western Plus Keene Hotel
1 bedroom, premium bedding, individually decorated

Best Western Plus Keene Hotel

3.0 star property
8.4 out of 10, Very good, (1000)
"It was a great stay"
The price is S$208
includes taxes & fees
24 Aug - 25 Aug
Best Western Plus Keene Hotel
Lincoln Inn & Gallery
Interior

Lincoln Inn & Gallery

3.0 star property
9.4 out of 10, Exceptional, (33)
"This place was great I cannot say enough about the innkeepers and the staff all in all you'll love it!!"
The price is S$236
includes taxes & fees
24 Aug - 25 Aug
Lincoln Inn & Gallery
Kimpton Taconic Hotel by IHG
Meeting facility

Kimpton Taconic Hotel by IHG

4.0 star property
9.4 out of 10, Exceptional, (794)
"Very nice property with friendly staff; excellent food at the restaurant; was only there for 16 hours but definitely want to go back to stay longer."
The price is S$302
includes taxes & fees
1 Sept - 2 Sept
Kimpton Taconic Hotel by IHG
Riverside Hotel, Ascend Hotel Collection
Sun deck

Riverside Hotel, Ascend Hotel Collection

2.5 star property
9.6 out of 10, Exceptional, (589)
"Lovely, and very peaceful stay nestled beside the Connecticut River"
The price is S$212
includes taxes & fees
26 Aug - 27 Aug
Riverside Hotel, Ascend Hotel Collection
The Manchester View
Property grounds

The Manchester View

2.5 star property
9.4 out of 10, Exceptional, (744)
"We enjoyed our stay. Clean, great staff, great continental breakfast!"
The Manchester View
Travelodge by Wyndham Brattleboro VT
Reception

Travelodge by Wyndham Brattleboro VT

2.5 star property
6.0 out of 10, (697)
"I was only there for a few hours sleep "
The price is S$100
includes taxes & fees
14 Sept - 15 Sept
Travelodge by Wyndham Brattleboro VT
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Free daily on-the-go breakfast

Holiday Inn Express Hotel & Suites Brattleboro by IHG

2.5 star property
8.8 out of 10, Excellent, (1000)
"Good room, great breakfast options "
The price is S$241
includes taxes & fees
31 Aug - 1 Sept
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Pointe at Castle Hill Resort
Indoor pool

Pointe at Castle Hill Resort

3.5 star property
8.8 out of 10, Excellent, (865)
"Will definitely stay here again! Very clean room nice and quiet and staff were very personable!"
The price is S$188
includes taxes & fees
25 Aug - 26 Aug
Pointe at Castle Hill Resort
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Exterior

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3.0 star property
9.0 out of 10, Wonderful, (732)
"Great place great scenery amazing staff"
The price is S$175
includes taxes & fees
1 Sept - 2 Sept
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
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.
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Where to stay in Chester

Find the best Chester areas for the activities you enjoy most.

Chester Depot

2 out of top 10 points of interest in this area

If you're spending some time in Chester Depot, DaVallia Art & Accents and Bonnie's Bundles Dolls are top sights worth seeing.

Learn more about Chester

Quaint Chester awaits: its hiking, skiing, mountain views and more!

See all hotels in Chester

Top Chester Hotel Reviews

The Shire Woodstock

The Shire Woodstock

10/10 Excellent
"Forth time at The Shire, everything was wonderful!! "
Judith 1-night trip
Posted 2 days ago
The Shire Woodstock

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.

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 dog-friendly accommodation option in Chester?

Motel in the Meadow is a top dog-friendly option for your stay. See more pet-friendly hotel accommodations in Chester.

What are some accommodation options with pools in Chester?

Woodstock Inn & Resort: Features a seasonal outdoor pool, an indoor pool and 4 restaurants. The Equinox Golf Resort & Spa and Colonial Motel And Spa are two additional hotels that feature an on-site pool. View all hotels with pools 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 67 hotels and other accommodation options to choose from. Find out more about Chester.

What should I do while I'm visiting Chester?

A couple of favourite places to visit are DaVallia Art & Accents and Bonnie's Bundles Dolls. You'll also find Vermont Country Store and Plummer's Sugar House in the area. Take a look at what more there is 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 temperature of 18°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Chester are January, March, November and February, with each month seeing an average of 35 cm of snowfall.