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

Smart TV, fireplace, stereo

LUXE Forest Retreat

LUXE Forest Retreat
Chester
The price is €413
includes taxes & fees
14 Apr - 15 Apr
LUXE Forest Retreat
Interior

Historic 150-year-old farmhouse, Jacuzzi included

Historic 150-year-old farmhouse, Jacuzzi included
Chester Depot
9.8 out of 10, Exceptional, (16 reviews)
The price is €353
includes taxes & fees
14 Apr - 15 Apr
Historic 150-year-old farmhouse, Jacuzzi included
Deluxe Suite | Private kitchen

Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (571 reviews)
  • cleanliness
    Family-friendly motel offers fun by the river with firepit activities, cosy rooms, and easy access to outdoor adventures.
The price is €102
includes taxes & fees
14 Apr - 15 Apr
Sleep Woodstock Motel
Land view from property

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (27 reviews)
The price is €121
includes taxes & fees
14 Apr - 15 Apr
Four Columns Inn
Property grounds

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very good, (1,002 reviews)
  • cleanliness
    Fun family adventures await with easy beach access, cosy rooms, and thoughtful in-room amenities for all ages.
The price is €79
includes taxes & fees
16 Apr - 17 Apr
The Putney 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 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 €133
includes taxes & fees
14 Apr - 15 Apr
Best Western Plus Keene Hotel
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, (180 reviews)
  • cleanliness
    Family fun awaits in the mountains with easy lake access, outdoor playground, and cosy firepit for evening entertainment.
The price is €113
includes taxes & fees
14 Apr - 15 Apr
Aerie Inn of Vermont
Lobby

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (792 reviews)
The price is €133
includes taxes & fees
16 Apr - 17 Apr
Comfort Inn & Suites Brattleboro I-91
Exterior

Deerfield Valley Inn

Deerfield Valley Inn
2.0 star property
West Dover
9.4 out of 10, Exceptional, (115 reviews)
  • cleanliness
    Family-friendly mountain retreat near Mount Snow offers delightful activities for kids with a cosy firepit for evening s'mores.
The price is €99
includes taxes & fees
14 Apr - 15 Apr
Deerfield Valley Inn
Outdoor dining

Stanford House

Stanford House
2.5 star property
Manchester Center
9.2 out of 10, Wonderful, (74 reviews)
The price is €106
includes taxes & fees
14 Apr - 15 Apr
Stanford House
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

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

8/10 Good
"The courtyard is fenced in, perfect for kids to get fresh air, the pool was clean and welcoming. Breakfast was delicious, so many options! Having the restaurant right there made dinner a breeze! Will definitely stay again!"
Rachel 1-night trip
Posted 6 hours ago
Best Western Plus Keene 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.