5/5 - Excellent
Verified traveler
Mar 1, 2020Very friendly area and quaint!
Chester, VT
Travel Guide
Where to stay in Chester
Chester Depot
4.5/5(15 area reviews)
If you're spending some time in Chester Depot, Bonnie's Bundles Dolls and DaVallia Art & Accents are top sights worth seeing.
Stone Hearth Inn and Eatery
698 VT-11, Chester, VT
The price is $233 per night from Jun 2 to Jun 3
$233
$254 total
includes taxes & fees
2 Jun - 3 Jun
Stay at this B&B in Chester. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Bonnie's Bundles Dolls and DaVallia Art & Accents are located ...
9/10 Wonderful! (45 reviews)
"My fiance and I had an amazing stay here. Vicki and her staff are incredible and attentive to their guests. The food is beyond amazing one of the best meals we have had. We highly recommend this cute and quaint spot and definitely will be making many trips back!"
Reviewed on 26 May 2024
Colonial Motel And Spa
889 Putney Rd, Brattleboro, VT
The price is $98 per night from Jun 2 to Jun 3
$98
$108 total
includes taxes & fees
2 Jun - 3 Jun
Stay at this 3-star spa motel in Brattleboro. Enjoy free WiFi, free parking, and 2 indoor pools. Our guests praise the helpful staff and the clean rooms in our ...
6.8/10 (1,002 reviews)
"I got the 1 bedroom suite there. It was very spacious and comfortable. The perfect place if you want to sleep well. The bedding was ultra comfortable and I had everything I needed."
Reviewed on 30 May 2024
Woodstock Inn & Resort
Fourteen The Green, Woodstock, VT
The price is $379 per night from Jun 2 to Jun 3
$379
$457 total
includes taxes & fees
2 Jun - 3 Jun
Book a stay at this luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Popular attractions Woodstock Town Hall Theatre and ...
9.2/10 Wonderful! (443 reviews)
"Lovely inn, always taking great care of visitors."
Reviewed on 28 May 2024
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.
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
Ludlow
Stay at this vacation home in Ludlow. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Okemo Mountain Resort and Lake Rescue are located ...
9.4/10 Exceptional! (20 reviews)
Lake House
"My family really enjoyed this Lake House. The beautiful views of the lake were breathtaking. The house had everything we needed for preparing meals. The kitchen was functional and generally well equipped. The beds in the house were particularly comfortable. We enjoyed early morning coffee on the ..."
Reviewed on 28 Apr 2024
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
3387 East Mountain Road, Killington, VT
Stay at this 3-star ski cabin in Killington. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Killington Resort and Skyeship Express ...
9/10 Wonderful! (32 reviews)
"Will be back!!"
Reviewed on 4 Mar 2024
Long Trail House at Stratton Mountain Resort
761 Stratton Access Rd, Stratton, VT
Stay at this 3-star spa aparthotel in Stratton. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Stratton Mountain Resort and Villager ...
8.4/10 Very Good! (69 reviews)
Walk to Mountain, Nice Unit at Stratton Villag
"The unit was perfect for our ski race weekend. Very accessible, underground parking included (ski boxes on top of SUVs will not fit - thankfully we left ours at home), really nice place with everything we needed!"
Reviewed on 22 May 2024
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.
Popular places to visit
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.
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.
Reviews of Chester
4.2
Top Destination
4/5 - Good
Verified traveler
Oct 19, 2019Quaint and beautiful town with good representation of Vermont.
4/5 - Good
Verified traveler
Feb 19, 2019Cute, quiet little town.
5/5 - Excellent
BL
Jan 22, 2019Chester is a cute little town. We went to ski at Okemo and this was the last place available, so we stumbled onto this property. Glad we did, going out to eat was much easier than in Ludlow and everyone we met couldn't be nicer.
4/5 - Good
Verified traveler
Jan 11, 2019The Scottish Inn Pub was excellent!
3/5 - Okay
Verified traveler
Oct 14, 2018Not much to it
- Bonnie's Bundles Dolls
- DaVallia Art & Accents
- Mount Snow
- Killington Resort
- Okemo Mountain Resort
- Stratton Mountain Resort
- Bromley Mountain Ski Resort
- Keene State College
- Equinox Preservation Trust
- Vermont Country Store
- Connecticut River
- Stratton Mountain Summit Gondola
- Magic Mountain Ski Resort
- Golf Club at Equinox
- Hildene
- Mount Snow Golf Course
- Spofford Lake
- Billings Farm and Museum
- Mt Ascutney State Park
- The Stone Church
- Battenkill River
- Landmark College
- Bellows Falls Opera House
- Connecticut Lakes Region
- Historic Main Street
- Blow-Me-Down Bridge
- Brattleboro Common
- Colonial Theatre
- Weston Playhouse
- American Express Ski Lift