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Check availability on Chester Family Hotels

Our top choices for 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, (111 reviews)
The price is ￥40,348
￥43,979 total
includes taxes & fees
Feb 18 - Feb 19
Stone Hearth Inn and Eatery
Children's area

Cozy 4bd - Ski Okemo, Killington, Magic & Bromley

Cozy 4bd - Ski Okemo, Killington, Magic & Bromley
Chester
10.0 out of 10, Exceptional, (11 reviews)
The price is ￥41,034
￥82,760 total
includes taxes & fees
Feb 10 - Feb 11
Cozy 4bd - Ski Okemo, Killington, Magic & Bromley
Interior

Historic 150-year-old farmhouse, Jacuzzi included

Historic 150-year-old farmhouse, Jacuzzi included
Chester Depot
9.8 out of 10, Exceptional, (14 reviews)
The price is ￥31,130
￥79,415 total
includes taxes & fees
Feb 10 - Feb 11
Historic 150-year-old farmhouse, Jacuzzi included
Lobby

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (760 reviews)
The price is ￥19,351
￥21,286 total
includes taxes & fees
Mar 5 - Mar 6
Comfort Inn & Suites Brattleboro I-91
Children's activities

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa
4.5 star property
Manchester Village Historic District
7.4 out of 10, Good, (594 reviews)
  • cleanliness
    Discover adventure for all ages with an indoor pool, seasonal outdoor pool, arcade, and tennis courts in this family haven.
The price is ￥23,026
￥33,951 total
includes taxes & fees
Feb 11 - Feb 12
The Equinox Golf Resort & Spa
Land view from property

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.6 out of 10, Exceptional, (20 reviews)
Four Columns Inn
Restaurant

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very Good, (1,003 reviews)
  • cleanliness
    A family vacation haven where kids splash in the indoor pool while parents relax—the perfect balance of fun and comfort at every age.
The price is ￥21,854
￥23,712 total
includes taxes & fees
Feb 10 - Feb 11
Best Western Plus Keene Hotel
Sundeck

Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel
2.5 star property
West Chesterfield
9.6 out of 10, Exceptional, (637 reviews)
  • cleanliness
    Family fun by the river with spacious rooms, cable TV, and nearby bowling—perfect for children.
The price is ￥23,921
￥25,955 total
includes taxes & fees
Mar 10 - Mar 11
Riverside Hotel, an Ascend Collection Hotel
Property grounds

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very Good, (1,003 reviews)
  • cleanliness
    Fun family adventures await with easy beach access, cozy rooms, and thoughtful in-room amenities for all ages.
The Putney Inn
Deluxe Suite | Private kitchen | Mini-fridge, microwave, coffee/tea maker, freezer

Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (556 reviews)
  • cleanliness
    Family-friendly motel offers fun by the river with firepit activities, cozy rooms, and easy access to outdoor adventures.
The price is ￥11,461
￥22,434 total
includes taxes & fees
Mar 9 - Mar 10
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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Choose what matters most at family-friendly hotels in Chester

Breakfast included
Pool

Top Chester Hotel Reviews

The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort

10/10 Excellent
"Accommodating staff"
Robert 1-night trip
Posted 4 days ago
The Black Bear Lodge at Stratton Mountain Resort

Frequently asked questions

What's Chester like for family-friendly vacations?
You might 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 vacation. 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 center.
What's the best place to stay for a family vacation 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 vacation in Chester?
The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Chester are January, March, November, and February, with each month seeing an average of 14 inches of snowfall.
What's there to see and do with your family in Chester?
While you are vacationing in Chester, you and the family might want to see interesting spots such as Bonnie's Bundles Dolls and DaVallia Art & Accents. Make sure you have plenty of time to take in activities in the area like Okemo Mountain Resort and Stratton Mountain Resort.