Chester Travel Guide

Tourist 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 and homes. 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, 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 AU$200 per night from 10 Mar to 11 Mar
AU$200
10 Mar - 11 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 ...
8.2/10 Very Good! (420 reviews)
The hotel bed sinks . My partner and I woke up with terrible stiffness and back pain. We could not sta another night there ( we booked 3 nights ) and stayed at another hotel for one night. The bed was so uncomfortable that we decided to end our trip a day early rather than stay there. Overall the ...

Reviewed on 24 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 AU$220 per night from 7 Apr to 8 Apr
AU$220
7 Apr - 8 Apr
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! (1,003 reviews)
nice lobby

Reviewed on 4 Mar 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 AU$546 per night from 15 Mar to 16 Mar
AU$546
15 Mar - 16 Mar
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! (566 reviews)
Amazing restaurant and attentive staff

Reviewed on 4 Mar 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.
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 Wi-Fi, an in-room coffee maker and in-room fireplaces. Popular attractions Okemo Mountain Resort and Phineas Gage Memorial ...
10/10 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 Feb 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
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 ...
8.6/10 Excellent! (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
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms

Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms

Wardsboro VT
Stay at this golf holiday home in Wardsboro. Enjoy free Wi-Fi, private pools and a fitness centre. Popular attractions Stratton Mountain Resort and Margie's ...
9.4/10 Exceptional! (30 reviews)
We had a wonderful Christmas week at Northern Quarters with our extended family, ages 5 months to 89 years old. The host was very helpful and accessible. The surroundings were beautiful —especially loved the brook and woods lighted up at night. Beds were comfortable and the houses were equipped with ...

Reviewed on 26 Dec 2025

Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
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.

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Cities near Chester