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Our top choices for Chester family-friendly hotels

Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
3.0 star property
Chester
9.2 out of 10, Wonderful, (116 reviews)
The price is AED 698
AED 761 total
includes taxes & fees
2 Apr - 3 Apr
Stone Hearth Inn and Eatery

Historic 150-year-old farmhouse, Jacuzzi included

Historic 150-year-old farmhouse, Jacuzzi included
Chester Depot
9.8 out of 10, Exceptional, (15 reviews)
The price is AED 529
AED 1,604 total
includes taxes & fees
26 Mar - 27 Mar
Historic 150-year-old farmhouse, Jacuzzi included

Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (560 reviews)
  • cleanliness
    Family-friendly motel offers fun by the river with firepit activities, cozy rooms, and easy access to outdoor adventures.
Sleep Woodstock Motel

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very Good, (1,001 reviews)
  • cleanliness
    Fun family adventures await with easy beach access, cozy rooms, and thoughtful in-room amenities for all ages.
The Putney Inn

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (786 reviews)
The price is AED 519
AED 571 total
includes taxes & fees
30 Mar - 31 Mar
Comfort Inn & Suites Brattleboro I-91

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 547
AED 594 total
includes taxes & fees
26 Mar - 27 Mar
Best Western Plus Keene Hotel

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (26 reviews)
Four Columns Inn

Stanford House

Stanford House
2.5 star property
Manchester Center
9.2 out of 10, Wonderful, (72 reviews)
The price is AED 397
AED 477 total
includes taxes & fees
26 Mar - 27 Mar
Stanford House

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

RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Hinsdale
10.0 out of 10, Exceptional, (11 reviews)
The price is AED 331
AED 578 total
includes taxes & fees
26 Mar - 27 Mar
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options

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
5 Apr - 6 Apr
Aerie Inn of Vermont
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.