Chester, VT

Travel Guide

aerial view of the Quechee Covered Bridge, over the Ottauquechee River, Quechee Vermont
aerial view of the Quechee Covered Bridge, over the Ottauquechee River, Quechee Vermont

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Where to stay in Chester

panoramic view of colorful foliage in White mountain national forest in New Hampshire along Kancamagus highway

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.

Chester Depot
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
2940 State Route 103 Cavendish VT
$142 nightly
The price is $154 total per night from Mar 2 to Mar 3
$154 total
Mar 2 - Mar 3
Total with taxes and fees
Book a stay at this spa hotel in Cavendish. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in ...
8.8/10 Excellent! (975 reviews)
Nice & helpful staff, great location, clean

Reviewed on Feb 10, 2026

Pointe at Castle Hill Resort
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
$349 nightly
The price is $384 total per night from Feb 22 to Feb 23
$384 total
Feb 22 - Feb 23
Total with taxes and fees
Book a stay at this luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
9.2/10 Wonderful! (562 reviews)
Excellent hotel, staff well trained.

Reviewed on Jan 21, 2026

Woodstock Inn & Resort
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
3567 Main Street Route 7A Manchester VT
$172 nightly
The price is $189 total per night from Feb 23 to Feb 24
$189 total
Feb 23 - Feb 24
Total with taxes and fees
Book a stay at this luxury hotel in Manchester. Enjoy free parking, an outdoor pool, and a full-service spa. Popular attractions Golf Club at Equinox and American ...
7.2/10 Good! (594 reviews)
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Reviewed on Feb 2, 2026

The Equinox Golf Resort & Spa
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.
Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area

Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area

Chester VT
Stay at this cabin in Chester. Enjoy free WiFi, an in-room coffeemaker, and in-room fireplaces. Popular attractions Okemo Mountain Resort and Phineas Gage Memorial ...
9.8/10 Exceptional! (23 reviews)
Hidden gem!
This lovingly built off-grid glamping cabin is drenched with sun! It’s absolutely gorgeous! The kids enjoyed pumping their own water and sledding down the front hill. Paris is an excellent hostess- she answered all our questions very promptly & thoroughly. We cant wait to come back! Thank you!!!

Reviewed on Feb 24, 2025

Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
Long Trail House at Stratton Mountain Resort

Long Trail House at Stratton Mountain Resort

3 out of 5
761 Stratton Access Rd Stratton VT
Book a stay at this ski aparthotel in Stratton. Enjoy free WiFi, free parking, and 10 restaurants. Popular attractions Stratton Mountain Resort and Villager ...
8.4/10 Very Good! (83 reviews)
Great location - the room was very clean and spacious. You don't check in at the property but at another one nearby. Hot tub was nicely maintained

Reviewed on Jan 31, 2026

Long Trail House at Stratton Mountain Resort
Mount Snow Yurt: Hot Tub~Wood Stove~WiFi~EVcharger

Mount Snow Yurt: Hot Tub~Wood Stove~WiFi~EVcharger

Dover VT
Book a stay at this family-friendly campground in West Dover. Enjoy free WiFi, a sauna, and a garden. Popular attractions Mount Snow and Mount Snow Golf Course ...
8/10 Very Good! (2 reviews)
Place was amazing! Beautiful property and so unique. Being pet friendly was a huge plus! We had a wonderful time!

Reviewed on Sep 21, 2025

Mount Snow Yurt: Hot Tub~Wood Stove~WiFi~EVcharger
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

Reviews of Chester

4.2
Top Destination
5 - Excellent
6
5 - Excellent 29%
4 - Good
14
4 - Good 67%
3 - Okay
1
3 - Okay 5%
2 - Disappointing
0
2 - Disappointing 0%
1 - Terrible
0
1 - Terrible 0%

5/5 - Excellent

Verified traveler

Very friendly area and quaint!

4/5 - Good

Verified traveler

Quaint and beautiful town with good representation of Vermont.

4/5 - Good

Verified traveler

Cute, quiet little town.

5/5 - Excellent

BL

Chester 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

The Scottish Inn Pub was excellent!

3/5 - Okay

Verified traveler

Not much to it

Cities near Chester

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