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Check availability on Chester Family Hotels

Our top choices for Chester family-friendly hotels

LUXE Forest Retreat

LUXE Forest Retreat
Chester
The price is AED 1,113
AED 1,769 total
includes taxes & fees
14 May - 15 May
LUXE Forest Retreat

Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (579 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 249
AED 483 total
includes taxes & fees
14 May - 15 May
Sleep Woodstock Motel

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 cozy firepit for evening entertainment.
The price is AED 424
AED 462 total
includes taxes & fees
14 May - 15 May
Aerie Inn of Vermont

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very Good, (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 345
AED 380 total
includes taxes & fees
17 May - 18 May
The Putney Inn

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (38 reviews)
The price is AED 479
AED 522 total
includes taxes & fees
17 May - 18 May
Four Columns Inn

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 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 566
AED 614 total
includes taxes & fees
14 May - 15 May
Best Western Plus Keene Hotel

Stanford House

Stanford House
2.5 star property
Manchester Center
9.2 out of 10, Wonderful, (74 reviews)
The price is AED 366
AED 439 total
includes taxes & fees
8 Jun - 9 Jun
Stanford House

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (803 reviews)
The price is AED 523
AED 576 total
includes taxes & fees
1 Jun - 2 Jun
Comfort Inn & Suites Brattleboro I-91

On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1,006 reviews)
  • cleanliness
    Riverside fun awaits families at this Woodstock retreat where kids enjoy the children's pool, playground, and arcade games.
The price is AED 542
AED 731 total
includes taxes & fees
21 May - 22 May
On The River Inn

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, (993 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 493
AED 596 total
includes taxes & fees
19 May - 20 May
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.

Choose what matters most at family-friendly hotels in Chester

Top Chester Hotel Reviews

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.