Chester Hotel Guide - Family Friendly Hotels in Chester, Vermont

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Check availability on Chester Family Friendly Hotels

This weekend
29 May - 31 May
Next weekend
5 Jun - 7 Jun

Our top choices for Chester family-friendly hotels

Deluxe Suite | Private kitchen

Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (580 reviews)
  • cleanliness
    Family-friendly motel offers fun by the river with firepit activities, cosy rooms, and easy access to outdoor adventures.
The price is €104
includes taxes & fees
31 May - 1 Jun
Sleep Woodstock Motel
Property grounds

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.6 out of 10, Excellent, (1,000 reviews)
  • cleanliness
    Fun family adventures await with easy beach access, cosy rooms, and thoughtful in-room amenities for all ages.
The price is €89
includes taxes & fees
31 May - 1 Jun
The Putney Inn
Land view from property

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (39 reviews)
The price is €122
includes taxes & fees
3 Jun - 4 Jun
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, (995 reviews)
  • cleanliness
    Family escapes to Black Bear Lodge offer mountain adventure with convenient ski shuttles and a game room for kids.
The price is €155
includes taxes & fees
8 Jun - 9 Jun
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, (807 reviews)
The price is €130
includes taxes & fees
7 Jun - 8 Jun
Comfort Inn & Suites Brattleboro I-91
Property grounds

RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options

RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Hinsdale
9.8 out of 10, Exceptional, (14 reviews)
The price is €139
includes taxes & fees
8 Jun - 9 Jun
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Outdoor dining

Stanford House

Stanford House
2.5 star property
Manchester Center
9.2 out of 10, Wonderful, (74 reviews)
The price is €116
includes taxes & fees
2 Jun - 3 Jun
Stanford House
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, (182 reviews)
  • cleanliness
    Family fun awaits in the mountains with easy lake access, outdoor playground, and cosy firepit for evening entertainment.
The price is €119
includes taxes & fees
29 May - 30 May
Aerie Inn of Vermont
Restaurant

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very good, (1,000 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 €138
includes taxes & fees
7 Jun - 8 Jun
Best Western Plus Keene Hotel
Free continental breakfast on weekends

Four Winds Country Motel

Four Winds Country Motel
2.0 star property
Manchester Center
8.4 out of 10, Very good, (546 reviews)
  • cleanliness
    A serene family retreat with seasonal pool, playground, and spacious rooms perfect for creating lasting holiday memories.
The price is €103
includes taxes & fees
31 May - 1 Jun
Four Winds Country 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

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

2/10 Terrible
"The building needs a total rehab"
Susan 1-night trip
Posted 7 hours ago
Days Inn by Wyndham Keene NH

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.