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Chester Hotels from S$109

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Check prices for these dates

This weekend
24 Jul - 26 Jul
Next weekend
31 Jul - 2 Aug

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Our top choices for Chester hotels

Garden

1. Fullerton Inn

Fullerton Inn
2.5 star property
Chester Depot
8.2 out of 10, Very good, (442 reviews)
"The building was very quaint and had a historical vibe."
United States
Rick
The price is S$224
includes taxes & fees
26 Jul - 27 Jul
Fullerton Inn
Front of property

2. Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
3.0 star property
Chester
9.2 out of 10, Wonderful, (120 reviews)
"Friendly helpful clean. Bathroom clean. Nice pillows. A/c was super because it was very hot outside. Breakfast was very good"
United States
Kathleen
The price is S$282
includes taxes & fees
22 Jul - 23 Jul
Stone Hearth Inn and Eatery
Exterior

3. Best Western Springfield Hotel

Best Western Springfield Hotel
2.5 star property
Springfield
8.8 out of 10, Excellent, (868 reviews)
"Our stay was great. Staff was very friendly and helpful."
United States
Patricia
The price is S$254
includes taxes & fees
27 Jul - 28 Jul
Best Western Springfield Hotel
Lobby sitting area

4. The Hartness House

The Hartness House
3.0 star property
Springfield
8.2 out of 10, Very good, (348 reviews)
"Fantastic historic house in downtown Springfield, VT. A wonderful place to spend an evening or the weekend. Close to state parks, great restaurants, and kayaking. Wonderful place for a getaway."
United States
Dan
The price is S$249
includes taxes & fees
4 Aug - 5 Aug
The Hartness House
Lounge

5. Bromley View Inn

Bromley View Inn
3.5 star property
Bondville
9.0 out of 10, Wonderful, (452 reviews)
"staff actually treated you like family and not another customer & Clean room & relaxing backyard to watch the sunset & great breakfast"
United States
Josh
The price is S$109
includes taxes & fees
28 Jul - 29 Jul
Bromley View Inn
Restaurant

6. The Upper Pass Lodge at Magic Mountain

The Upper Pass Lodge at Magic Mountain
2.5 star property
Londonderry
8.2 out of 10, Very good, (701 reviews)
"Charming rustic inn. Staff were delightful and food was great. "
United States
Bradley
The price is S$156
includes taxes & fees
19 Aug - 20 Aug
The Upper Pass Lodge at Magic Mountain
Premium bedding, in-room safe, iron/ironing board, free WiFi

7. Claremont Motor Lodge

Claremont Motor Lodge
2.5 star property
Claremont
8.8 out of 10, Excellent, (544 reviews)
"Nice place to stay"
United States
Shane
The price is S$142
includes taxes & fees
22 Jul - 23 Jul
Claremont Motor Lodge
Interior

8. The Inn at Weathersfield

The Inn at Weathersfield
4.0 star property
Perkinsville
9.8 out of 10, Exceptional, (80 reviews)
"Great location, service and restaurant "
United States
LUDJANE
The price is S$290
includes taxes & fees
22 Jul - 23 Jul
The Inn at Weathersfield
Sauna, aromatherapy, hot stone massages, deep-tissue massages

9. Pointe at Castle Hill Resort

Pointe at Castle Hill Resort
3.5 star property
Cavendish
8.8 out of 10, Excellent, (1,003 reviews)
"Great place for the family!"
United States
Stephen
The price is S$199
includes taxes & fees
9 Aug - 10 Aug
Pointe at Castle Hill Resort
Kayaking

10. Blue Gentian Lodge at Magic Mountain

Blue Gentian Lodge at Magic Mountain
2.5 star property
Londonderry
9.2 out of 10, Wonderful, (120 reviews)
"Lovely stay near Magic Mountain. "
United States
Abigail
The price is S$210
includes taxes & fees
27 Jul - 28 Jul
Blue Gentian Lodge at Magic Mountain
Porch

11. Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (268 reviews)
"Amazing property and hosts...If you are looking for a quiet getaway with a river view and gourmet breakfast, look no further!"
United States
Paul
The price is S$220
includes taxes & fees
18 Aug - 19 Aug
Harvest Barn Inn
Interior entrance

12. The Common Man Inn & Restaurant

The Common Man Inn & Restaurant
3.5 star property
Claremont
9.6 out of 10, Exceptional, (404 reviews)
"Beautifully decorated old mill right on the river with great restaurant"
United States
Denis
The price is S$207
includes taxes & fees
26 Jul - 27 Jul
The Common Man Inn & Restaurant
Front of property ā€“ evening/night

13. Main and Mountain Bar & Motel

Main and Mountain Bar & Motel
2.0 star property
Ludlow
9.6 out of 10, Exceptional, (224 reviews)
"Comfy beds , great shower and awesome coffee room !"
United States
Kristina
The price is S$207
includes taxes & fees
27 Jul - 28 Jul
Main and Mountain Bar & Motel
Lobby lounge

14. Sun Lodge, an Ascend Collection Hotel

Sun Lodge, an Ascend Collection Hotel
3.5 star property
Bromley Mountain
8.8 out of 10, Excellent, (340 reviews)
"The staff here are fantastic and super helpful. What a great crew. Hotel was neat and clean. It was nice having a balcony view."
United States
Joe
The price is S$158
includes taxes & fees
20 Aug - 21 Aug
Sun Lodge, an Ascend Collection Hotel
Free WiFi, bed sheets

15. The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort
3.0 star property
Stratton
7.6 out of 10, Good, (1,002 reviews)
"The beds were very squeaky. Pillows too big"
United States
Patti
The price is S$193
includes taxes & fees
27 Jul - 28 Jul
The Black Bear Lodge at Stratton Mountain Resort
Exterior

16. The Landgrove

The Landgrove
3.5 star property
Londonderry
10.0 out of 10, Exceptional, (1 review)
"Tammy, the assistant inn keeper and restaurant manager was fantastic. She was attentive to every need. The restaurant staff was phenomenal as well highly recommend, itā€™s a little hidden gem off the beaten path. I will definitely return. Had a fabulous time."
United States
Andrea
The price is S$252
includes taxes & fees
23 Jul - 24 Jul
The Landgrove
Desk, blackout curtains, iron/ironing board, free WiFi

17. Royal Inn Claremont

Royal Inn Claremont
2.0 star property
Claremont
6.8 out of 10, (345 reviews)
"I like it was clean bathroom was new."
United States
Eva
The price is S$139
includes taxes & fees
22 Jul - 23 Jul
Royal Inn Claremont
Exterior

18. Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG
3.0 star property
Brownsville
9.0 out of 10, Wonderful, (858 reviews)
"Location of resort is beautiful!! We were not there very long or at resort for many hours but was well kept, beautiful area. Clean and well stocked. Would definitely return."
United States
Carol
The price is S$181
includes taxes & fees
27 Jul - 28 Jul
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Living area

19. Brittany Motel

Brittany Motel
2.0 star property
Manchester Center
9.4 out of 10, Exceptional, (387 reviews)
"The property was comfortable. Felt safe and the room was cozy and nicely decorated"
United States
Samantha
The price is S$122
includes taxes & fees
22 Jul - 23 Jul
Brittany Motel
Property entrance

20. Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property
3.0 star property
Jackson Gore Base Area
8.6 out of 10, Excellent, (872 reviews)
"Great family friendly location!"
United States
Cynthia
The price is S$299
includes taxes & fees
20 Aug - 21 Aug
Jackson Gore Village, A Vail Resorts Property
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.
A forest with autumn foliage in various colors.

Chester Depot

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

Stay near popular Chester attractions

DaVallia Art & Accents

10.0/10 (2 reviews)
This Vermont art haven showcases fine local art and handcrafted furniture in thoughtfully designed spaces. Browse both the Art Boutique and 39 North Gallery to experience indoor exhibits and outdoor sculpture gardens.
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Learn more about Chester

Nestled in a relaxing small-town setting, Chester invites visitors to explore DaVallia Art & Accents and browse handcrafted treasures at Bonnie's Bundles Dolls. Outdoor enthusiasts can enjoy nearby Stoughton Pond Recreation Area or take a scenic drive to Lowell Lake State Park and the charming Vermont Country Store.

See all hotels in Chester
A nighttime view of a large, illuminated bridge with intricate metalwork and a prominent arch.

Top Chester Hotel Reviews

On The River Inn

On The River Inn

10/10 Excellent
"Is just charming, peaceful and with that Vermont character."
Julio 2-night trip
Posted 18 hours ago
On The River Inn

More cheap stays in Chester

Hampton Inn Brattleboro

Hampton Inn Brattleboro

1378 Putney Road Brattleboro VT
The price is S$177 per night from 3 Aug to 4 Aug
S$177
3 Aug - 4 Aug
includes taxes & fees
8.2/10 Very good! (1,003 reviews)

Frequently asked questions

Where is the best place to stay in Chester?
Based on our traveller data, Fullerton Inn is one of the top choices for your stay. This inn offers free breakfast and a restaurant. Other good choices for your stay in the area are Woodstock Inn & Resort and Keene Elm City Hotel, an Ascend Collection Hotel. See all available top hotels, or vacation rentals in Chester.
What are some of the best holiday rentals that Chester has to offer?
Okemo Mountain Lodging by Vail Resorts: This holiday home rental outside of Chester is in the mountains and offers an LCD TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a dishwasher and a stovetop. 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 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: Provides a seasonal outdoor pool, an indoor pool and 4 restaurants. Keene Elm City Hotel, an Ascend Collection Hotel and Kimpton Taconic Hotel by IHG 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 64 hotels and other accommodation options to choose from. Find out more about Chester.
What should I do while I'm visiting Chester?
Attractions like DaVallia Art & Accents and Bonnie's Bundles Dolls are fun for everyone. You'll also find Vermont Country Store and Lowell Lake State Park 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 18Ā°C, while the coldest months are January and February, with an average of -4Ā°C. The snowiest months in Chester are January, March, November and February, with each month seeing an average of 35 cm of snowfall.

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