Chester

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

The Annual Holiday Sale

Members save up to 40% on hotels. Plan this year’s big trip and save.

Where to stay in Chester

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

Chester Depot

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

Chester Depot
Fullerton Inn

Fullerton Inn

2.5 out of 5
40 The Common Chester VT
The price is S$178 per night from 17 Mar to 18 Mar
S$178
17 Mar - 18 Mar
includes taxes & fees
Stay at this inn in Chester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms in their reviews. Popular ...
8/10 Very Good! (416 reviews)
Friendliness, ease of checkin and iut

Reviewed on 14 Feb, 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 S$207 per night from 17 Mar to 18 Mar
S$207
17 Mar - 18 Mar
includes taxes & fees
Stay at this spa hotel in Cavendish. Enjoy free Wi-Fi, free parking and a full-service spa. Our guests praise the helpful staff and the clean rooms in their ...
8.8/10 Excellent! (975 reviews)
Nice & helpful staff, great location, clean

Reviewed on 10 Feb, 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 S$485 per night from 22 Feb to 23 Feb
S$485
22 Feb - 23 Feb
includes taxes & fees
Stay at this luxury resort in Woodstock. Enjoy free Wi-Fi, free valet parking and an outdoor pool. Our guests praise the helpful staff in their reviews. Popular ...
9.2/10 Wonderful! (562 reviews)
Excellent hotel, staff well trained.

Reviewed on 21 Jan, 2026

Woodstock Inn & Resort
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.
Long Trail House at Stratton Mountain Resort

Long Trail House at Stratton Mountain Resort

3 out of 5
761 Stratton Access Rd Stratton VT
Stay at this ski aparthotel in Stratton. Enjoy free Wi-Fi, free parking and 10 restaurants. Popular attractions Stratton Mountain Resort and Villager Ski Lift ...
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 31 Jan, 2026

Long Trail House at Stratton Mountain Resort
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3 out of 5
3387 East Mountain Road Killington VT
Stay at this ski cabin in Killington. Enjoy free Wi-Fi, free parking and a sauna. Popular attractions Killington Resort and Pico Mountain at Killington Ski Resort ...
9/10 Wonderful! (58 reviews)
ample room, close to ski lifts, pretty view, great renovations, sauna was great, family had a wonderful time!

Reviewed on 22 Dec, 2025

Ski in & out Spruce Glen Townhomes on Great Eastern Trail
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