Chester Hotels from S$107
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5 Sept - 6 SeptTomorrow
6 Sept - 7 SeptNext weekend
11 Sept - 13 SeptIn two weeks
18 Sept - 20 SeptOur top choices for Chester hotels
1. Fullerton Inn
Fullerton InnChester Depot
Kirsty
S$192
includes taxes & fees
8 Sept - 9 Sept
2. Stone Hearth Inn and Eatery
Stone Hearth Inn and EateryChester
Kathleen
S$288
includes taxes & fees
7 Sept - 8 Sept
3. Best Western Springfield Hotel
Best Western Springfield HotelSpringfield
Gerry
S$224
includes taxes & fees
13 Sept - 14 Sept
4. Pointe at Castle Hill Resort
Pointe at Castle Hill ResortCavendish
David
S$183
includes taxes & fees
7 Sept - 8 Sept
5. The Upper Pass Lodge at Magic Mountain
The Upper Pass Lodge at Magic MountainLondonderry
Terry
S$124
includes taxes & fees
8 Sept - 9 Sept
6. The Inn at Weathersfield
The Inn at WeathersfieldPerkinsville
Rula
S$291
includes taxes & fees
12 Sept - 13 Sept
7. The Hartness House
The Hartness HouseSpringfield
Dan
S$247
includes taxes & fees
6 Sept - 7 Sept
8. Harvest Barn Inn
Harvest Barn InnBellows Falls
Michael
S$223
includes taxes & fees
8 Sept - 9 Sept
9. Bromley View Inn
Bromley View InnBondville
William
S$107
includes taxes & fees
8 Sept - 9 Sept
10. Blue Gentian Lodge at Magic Mountain
Blue Gentian Lodge at Magic MountainLondonderry
Abigail
S$208
includes taxes & fees
8 Sept - 9 Sept
11. Claremont Motor Lodge
Claremont Motor LodgeClaremont
EDWARD S
S$162
includes taxes & fees
8 Sept - 9 Sept
12. The Black Bear Lodge at Stratton Mountain Resort
The Black Bear Lodge at Stratton Mountain ResortStratton
Roberta
S$155
includes taxes & fees
7 Sept - 8 Sept
13. COHO Inn & Motor Lodge
COHO Inn & Motor LodgeWeston
Christopher
S$246
includes taxes & fees
6 Sept - 7 Sept
14. Main and Mountain Bar & Motel
Main and Mountain Bar & MotelLudlow
Paull
S$224
includes taxes & fees
14 Sept - 15 Sept
15. Jackson Gore Village, A Vail Resorts Property
Jackson Gore Village, A Vail Resorts PropertyJackson Gore Base Area
Zulma
S$268
includes taxes & fees
30 Sept - 1 Oct
16. The Manchester View
The Manchester ViewManchester Center
Jason
S$116
includes taxes & fees
8 Sept - 9 Sept
17. Castle Hill Resort And Spa
Castle Hill Resort And SpaCavendish
Mirco
S$272
includes taxes & fees
7 Sept - 8 Sept
18. Sun Lodge near Manchester VT, Ascend Collection Hotel
Sun Lodge near Manchester VT, Ascend Collection HotelBromley Mountain
Terry
S$177
includes taxes & fees
27 Sept - 28 Sept
19. The Landgrove
The LandgroveLondonderry
Andrea
S$231
includes taxes & fees
7 Sept - 8 Sept
20. Comfort Inn & Suites Brattleboro I-91
Comfort Inn & Suites Brattleboro I-91Brattleboro
Ellen
S$165
includes taxes & fees
13 Sept - 14 Sept
Where to stay in Chester
Find the best Chester areas for the activities you enjoy most.
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.
Bonnie's Bundles Dolls
7.6/10 (4 reviews)
This historic Vermont studio showcased handcrafted cloth dolls with embroidered faces and calico clothing. Visitors treasured personal interactions with artist Bonnie Watters and stories behind her creations.
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
Top Chester Hotel Reviews
Keene Elm City Hotel, an Ascend Collection Hotel
10/10 Excellent
"All around great stay. Thank you."
The Jackson
10/10 Excellent
"We had a lovely 1 night stay at the quaint Jackson. We enjoyed the wine & cheese hour, had dinner at Oakes & Evelyn (on site but not part of the hotel) and enjoyed a nightcap on the porch. The bed was super comfortable, sheets were clean and crisp, robes were Frette and products smelled great. The property is gorgeous and Woodstock as a town is a delight."
The Manchester View
10/10 Excellent
"This property checks all of the boxes. The views of surrounding mountains are among the best in the area. The rooms were recently updated and very comfortable. The location is just a small 1 mile drive to the village and great restaurants."
Kimpton Taconic Hotel by IHG
8/10 Good
"My room had candy on side table and needed to have phone cleaned. Older property has character but needs attention in rooms. Don't pay for valet parking basically the same as self parking. Upon check out they handed me the keys to get car. I think it was overpriced for what you get. Manchester is a cute town. Nothing in the room to make coffee and had to buy water no refrigerators as well"
Woodstock Inn & Resort
10/10 Excellent
"Beautiful as is the town"
Hampton Inn and Suites Manchester
10/10 Excellent
"Love the HI in Manchester VT. Great location"
More cheap stays in Chester
The Manchester View
77 High Meadow Way & VT-7A Manchester Center VT
S$116
8 Sept - 9 Sept
includes taxes & fees
9.4/10 Exceptional! (878 reviews)
Claremont Motor Lodge
16 Beauregard St Claremont NH
S$162
8 Sept - 9 Sept
includes taxes & fees
Hampton Inn Brattleboro
1378 Putney Road Brattleboro VT
S$170
13 Sept - 14 Sept
includes taxes & fees
Keene Elm City Hotel, an Ascend Collection Hotel
175 Key Rd Keene NH
S$194
9 Sept - 10 Sept
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
Hampton Inn and Suites Manchester
4519 Main St Manchester Center VT
S$216
21 Sept - 22 Sept
includes taxes & fees
9.6/10 Exceptional! (1,000 reviews)
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- Visit Andover
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