Chester Hotel Guide - Family Friendly Hotels in Chester, Vermont

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Check availability on Chester Family Friendly Hotels

Tonight
28 Nov - 29 Nov
Tomorrow
29 Nov - 30 Nov
This weekend
28 Nov - 30 Nov
Next weekend
5 Dec - 7 Dec

Top Chester Family Friendly Hotels

Front of property
Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

3.0 star property
Chester
9.2 out of 10, Wonderful, (106)
"Good breakfast and dinner options. Great location for hiking."
United States
Paul
The price is €196
includes taxes & fees
1 Dec - 2 Dec
Stone Hearth Inn and Eatery
Interior
Whimsical Room & Private Bathroom in Historic Inn

Whimsical Room & Private Bathroom in Historic Inn

Chester Depot
8.8 out of 10, Excellent, (9)
"After a long month of work I needed a weekend in VT to calm the nerves. This was a beautiful spot to be in, glad I was here!"
United States
Paul S.
The price is €148
includes taxes & fees
30 Nov - 1 Dec
Whimsical Room & Private Bathroom in Historic Inn
1 bedroom, desk, iron/ironing board, free WiFi
Honeymoon Suite with Jacuzzi Tub in Historic Inn

Honeymoon Suite with Jacuzzi Tub in Historic Inn

Chester Depot
8.6 out of 10, Excellent, (7)
"Charming place, hope to go back soon."
United States
Sharon S.
The price is €302
includes taxes & fees
11 Dec - 12 Dec
Honeymoon Suite with Jacuzzi Tub in Historic Inn
Interior
King & Queen Suite in Historic Inn Circa 1780

King & Queen Suite in Historic Inn Circa 1780

Chester Depot
9.8 out of 10, Exceptional, (16)
"Central for our needs. easy check in process. Lovely large room with comfy beds. "
United States
HIlary H.
The price is €357
includes taxes & fees
11 Dec - 12 Dec
King & Queen Suite in Historic Inn Circa 1780
Children’s activities
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 star property
Manchester
7.4 out of 10, Good, (571)
"Nice old Inn!"
United States
Daniel
The price is €175
includes taxes & fees
7 Dec - 8 Dec
The Equinox Golf Resort & Spa
Lobby lounge
Sun Lodge

Sun Lodge

3.5 star property
Bromley Mountain
8.6 out of 10, Excellent, (297)
"Everything was fantastic from check-in the restaurant, the bar, the staff and just surrounding every area very very nice people would definitely come back back again"
United States
Beth
The price is €105
includes taxes & fees
30 Nov - 1 Dec
Sun Lodge
Lobby
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

2.5 star property
Brattleboro
8.6 out of 10, Excellent, (732)
"Absolutely perfect stay for a business trip"
United States
Lyndsey
The price is €114
includes taxes & fees
14 Dec - 15 Dec
Comfort Inn & Suites Brattleboro I-91
Garden
Four Columns Inn

Four Columns Inn

4.0 star property
Newfane
9.8 out of 10, Exceptional, (12)
"Cozy inn in a beautiful setting, and great staff and service"
United States
Archith
Four Columns Inn
Arcade
The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort

3.0 star property
Stratton
7.6 out of 10, Good, (935)
"Great place for the price "
United States
Karen
The price is €187
includes taxes & fees
1 Dec - 2 Dec
The Black Bear Lodge at Stratton Mountain Resort
Deluxe Suite
Sleep Woodstock Motel

Sleep Woodstock Motel

2.0 star property
Woodstock
9.6 out of 10, Exceptional, (544)
"Clean, friendly, easy check in, welcoming accommodations. Can’t wait to come back"
United States
David
The price is €111
includes taxes & fees
3 Dec - 4 Dec
Sleep Woodstock Motel
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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Top Chester Hotel Reviews

Woodstock Inn & Resort

Woodstock Inn & Resort

10/10 Excellent
"Top notch service. Great property and beautiful room. Went for anniversary and it did not disappoint. Romantic hotel and town"
Zachary 1-night trip
Posted 1 day ago
Woodstock Inn & Resort

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Frequently asked questions

What's Chester like for family-friendly holidays?
You may want to consider the relaxing destination of Chester if you've been thinking about a trip for the whole family. The chocolate shops, restaurants and hiking trails are just a few of the things that make this an attractive spot for a family holiday. Arrange a flight into Springfield, VT (VSF-Hartness State), which is the closest airport, or Rutland, VT (RUT-Rutland Southern Vermont Regional), which is located 25.4 mi (40.8 km) from the city centre.
What's the best family accommodation in Chester?
1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO! is a guesthouse with in-room kitchens and laundry facilities, and it's a top choice on Expedia for families.
When's the best time to book a family-friendly holiday in Chester?
The hottest months are usually July and August, with an average temperature of 18°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Chester are January, March, November and February, with each month seeing an average of 35 cm of snowfall.
What's there to see and do with your family in Chester?
While you are holidaying in Chester, you and the family may want to see some interesting spots such as DaVallia Art & Accents and Bonnie's Bundles Dolls. Make sure that you have lots of time for activities such as Vermont Country Store and Plummer's Sugar House.