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

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Check availability on Chester Family Hotels

Next weekend
3 Jul - 5 Jul
In two weeks
10 Jul - 12 Jul

Our top choices for Chester family-friendly hotels

Lobby

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (821 reviews)
The price is AED 415
AED 456 total
includes taxes & fees
2 Jul - 3 Jul
Comfort Inn & Suites Brattleboro I-91
Premier Quadruple Room, Garden View | Premium bedding, individually decorated, individually furnished

The Landgrove

The Landgrove
3.5 star property
Londonderry
10.0 out of 10, Exceptional, (1 review)
The price is AED 592
AED 645 total
includes taxes & fees
30 Jun - 1 Jul
The Landgrove
Restaurant

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very Good, (1,005 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 AED 467
AED 507 total
includes taxes & fees
1 Jul - 2 Jul
Best Western Plus Keene Hotel
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, (586 reviews)
  • cleanliness
    Family-friendly motel offers fun by the river with firepit activities, cozy rooms, and easy access to outdoor adventures.
The price is AED 289
AED 459 total
includes taxes & fees
19 Jul - 20 Jul
Sleep Woodstock Motel
Land view from property

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (44 reviews)
The price is AED 446
AED 486 total
includes taxes & fees
29 Jun - 30 Jun
Four Columns Inn
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, cozy rooms, and thoughtful in-room amenities for all ages.
The price is AED 400
AED 440 total
includes taxes & fees
30 Jun - 1 Jul
The Putney Inn
Property amenity

Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow
3.0 star property
West Dover
8.8 out of 10, Excellent, (109 reviews)
The price is AED 297
AED 327 total
includes taxes & fees
7 Jul - 8 Jul
Hideaway Inn Mt. Snow
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 cozy firepit for evening entertainment.
The price is AED 525
AED 573 total
includes taxes & fees
29 Jun - 30 Jun
Aerie Inn of Vermont
Reception

Travelodge by Wyndham Brattleboro VT

Travelodge by Wyndham Brattleboro VT
2.5 star property
Brattleboro
6.0 out of 10, (780 reviews)
The price is AED 288
AED 316 total
includes taxes & fees
16 Jul - 17 Jul
Travelodge by Wyndham Brattleboro VT
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, (998 reviews)
  • cleanliness
    Family escapes to Black Bear Lodge offer mountain adventure with convenient ski shuttles and a game room for kids.
The price is AED 499
AED 604 total
includes taxes & fees
1 Jul - 2 Jul
The Black Bear Lodge at Stratton Mountain Resort
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

Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

10/10 Excellent
"Property and staff were great!"
George 1-night trip
Posted 5 hours ago
Grand Summit Resort, A Vail Resorts Property

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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 DaVallia Art & Accents and Bonnie's Bundles Dolls. Make sure you have lots of time for activities like Vermont Country Store and Magic Mountain Ski Resort.