Chester, VT

Travel Guide

Where to stay in Chester

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Chester Depot

4.5/5(15 area reviews)

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

Chester Depot
Fullerton Inn

Fullerton Inn

2.5 out of 5
40 The Common Chester VT
The price is AED 474 per night from Jan 20 to Jan 21
AED 474
AED 516 total
20 Jan - 21 Jan
includes taxes & fees
Stay at this inn in Chester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
8/10 Very Good! (409 reviews)
Where to start!? If you like small town vibe with all the necessities close by I highly suggest this location. The building is absolutely gorgeous and is located on a little “service road” with a few shops and stores in easy walking distance. From front desk to restaurant staff, everyone was fun, ...

Reviewed on 6 January 2026

Fullerton Inn
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
2940 State Route 103 Cavendish VT
The price is AED 562 per night from Jan 28 to Jan 29
AED 562
AED 641 total
28 Jan - 29 Jan
includes taxes & 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! (956 reviews)
Everything/everyone was superb!!!

Reviewed on 17 January 2026

Pointe at Castle Hill Resort
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
The price is AED 1,429 per night from Jan 20 to Jan 21
AED 1,429
AED 1,733 total
20 Jan - 21 Jan
includes taxes & 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! (560 reviews)
Luxurious and friendly resort! Loved it

Reviewed on 18 December 2025

Woodstock Inn & Resort
See all 3,107 properties in Chester
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 24 February 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! (78 reviews)
Nice lodge. Room needs updating

Reviewed on 19 October 2025

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 21 September 2025

Mount Snow Yurt: Hot Tub~Wood Stove~WiFi~EVcharger
See all properties in Chester
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.

Bonnie's Bundles Dolls

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.

DaVallia Art & Accents

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