aerial view of the Quechee Covered Bridge, over the Ottauquechee River, Quechee Vermont

Chester Family Hotel

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Our top choices for Chester family-friendly hotels

Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (582 reviews)
  • cleanliness
    Family-friendly motel offers fun by the river with firepit activities, cosy rooms, and easy access to outdoor adventures.
The price is HK$591
HK$925 total
includes taxes & fees
23 Jun - 24 Jun
Sleep Woodstock Motel

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (819 reviews)
The price is HK$885
HK$973 total
includes taxes & fees
2 Jul - 3 Jul
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, (1,006 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 HK$934
HK$1,014 total
includes taxes & fees
25 Jun - 26 Jun
Best Western Plus Keene Hotel

Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow
3.0 star property
West Dover
8.8 out of 10, Excellent, (105 reviews)
The price is HK$699
HK$769 total
includes taxes & fees
24 Jun - 25 Jun
Hideaway Inn Mt. Snow

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (42 reviews)
The price is HK$1,023
HK$1,115 total
includes taxes & fees
23 Jun - 24 Jun
Four Columns Inn

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 HK$905
HK$987 total
includes taxes & fees
23 Jun - 24 Jun
Aerie Inn of Vermont

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, (996 reviews)
  • cleanliness
    Family escapes to Black Bear Lodge offer mountain adventure with convenient ski shuttles and a game room for kids.
The price is HK$1,168
HK$1,413 total
includes taxes & fees
24 Jun - 25 Jun
The Black Bear Lodge at Stratton Mountain Resort

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.6 out of 10, Excellent, (1,003 reviews)
  • cleanliness
    Fun family adventures await with easy beach access, cosy rooms, and thoughtful in-room amenities for all ages.
The price is HK$776
HK$853 total
includes taxes & fees
30 Jun - 1 Jul
The Putney Inn

Colonial Motel

Colonial Motel
3.0 star property
Brattleboro
5.2 out of 10, (7 reviews)
  • cleanliness
    Family fun abounds at this colonial motel with two indoor pools, spa services, and family dining options.
The price is HK$564
HK$621 total
includes taxes & fees
23 Jun - 24 Jun
Colonial Motel

On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1,003 reviews)
  • cleanliness
    Riverside fun awaits families at this Woodstock retreat where kids enjoy the children's pool, playground, and arcade games.
The price is HK$1,638
HK$1,931 total
includes taxes & fees
6 Jul - 7 Jul
On The River Inn
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 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 My Minds Design and Vermont Country Store.

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