A covered wooden bridge over a river, surrounded by rocky terrain and greenery.

Chester Hotel Guide - Family Friendly Hotels in Chester, Vermont

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Check availability on Chester Family Friendly Hotels

Our top choices for Chester family-friendly hotels

Restaurant

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very good, (1,017 reviews)
  • cleanliness
    A family holiday haven where kids splash in the indoor pool while parents relax—the perfect balance of fun and comfort at every age.
The price is €113
includes taxes & fees
2 Aug - 3 Aug
Best Western Plus Keene Hotel
Deluxe Suite | Private kitchen

Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (591 reviews)
  • cleanliness
    Family-friendly motel offers fun by the river with firepit activities, cosy rooms, and easy access to outdoor adventures.
The price is €75
includes taxes & fees
21 Jul - 22 Jul
Sleep Woodstock Motel
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, (1,004 reviews)
  • cleanliness
    Family escapes to Black Bear Lodge offer mountain adventure with convenient ski shuttles and a game room for kids.
The price is €142
includes taxes & fees
16 Jul - 17 Jul
The Black Bear Lodge at Stratton Mountain Resort
Lobby

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (833 reviews)
The price is €131
includes taxes & fees
11 Aug - 12 Aug
Comfort Inn & Suites Brattleboro I-91
Property amenity

Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow
3.0 star property
West Dover
8.8 out of 10, Excellent, (118 reviews)
The price is €86
includes taxes & fees
19 Jul - 20 Jul
Hideaway Inn Mt. Snow
Premier Quadruple Room, Garden View

The Landgrove

The Landgrove
3.5 star property
Londonderry
10.0 out of 10, Exceptional, (1 review)
The price is €201
includes taxes & fees
9 Aug - 10 Aug
The Landgrove
Property grounds

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very good, (1,006 reviews)
  • cleanliness
    Fun family adventures await with easy beach access, cosy rooms, and thoughtful in-room amenities for all ages.
The price is €110
includes taxes & fees
22 Jul - 23 Jul
The Putney Inn
Children’s play area – indoor

Aerie Inn of Vermont

Aerie Inn of Vermont
2.0 star property
East Dorset
9.4 out of 10, Exceptional, (183 reviews)
  • cleanliness
    Family fun awaits in the mountains with easy lake access, outdoor playground, and cosy firepit for evening entertainment.
The price is €126
includes taxes & fees
9 Aug - 10 Aug
Aerie Inn of Vermont
Lobby lounge

Sun Lodge, an Ascend Collection Hotel

Sun Lodge, an Ascend Collection Hotel
3.5 star property
Bromley Mountain
8.8 out of 10, Excellent, (339 reviews)
  • cleanliness
    Family fun at this ski-in/ski-out lodge offers game room adventures, mountain access, and recently renovated spaces.
The price is €114
includes taxes & fees
19 Jul - 20 Jul
Sun Lodge, an Ascend Collection Hotel
Fountain

Weathervane Motel

Weathervane Motel
2.0 star property
Manchester Center
6.8 out of 10, (783 reviews)
  • cleanliness
    Family paradise awaits with spacious rooms and kid-friendly entertainment near Green Mountain National Forest.
The price is €103
includes taxes & fees
14 Jul - 15 Jul
Weathervane 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

Latchis Hotel

Latchis Hotel

8/10 Good
"X"
Richard 1-night trip
Posted 11 hours ago
Latchis Hotel

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 Magic Mountain Ski Resort.