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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, (109 reviews)
"So great all around!"
United States
Janet
The price is AED 953
AED 1,039 total
includes taxes & fees
24 Feb - 25 Feb
Stone Hearth Inn and Eatery

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.6 out of 10, Exceptional, (19 reviews)
"Everything was great 👍 I will stay there again and highly recommend to others "
United States
Linda
Four Columns Inn

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (758 reviews)
"The room was clean and the staff was wonderful"
United States
Julianne
The price is AED 490
AED 539 total
includes taxes & fees
29 Jan - 30 Jan
Comfort Inn & Suites Brattleboro I-91

The Palmer House Resort, an Ascend Collection Hotel

The Palmer House Resort, an Ascend Collection Hotel
3.0 star property
Manchester Center
8.4 out of 10, Very Good, (880 reviews)
"Rooms were spotless and staff was great!"
United States
Helen
The price is AED 312
AED 404 total
includes taxes & fees
22 Feb - 23 Feb
The Palmer House Resort, an Ascend Collection Hotel

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very Good, (1,001 reviews)
"perfect room, very clean and friendly staff"
Canada
Marc-André
The Putney Inn

On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1,000 reviews)
"Brilliant stay"
United States
Enrico
The price is AED 871
AED 1,092 total
includes taxes & fees
12 Feb - 13 Feb
On The River Inn

Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown
2.5 star property
Keene
8.8 out of 10, Excellent, (759 reviews)
"Everything was clean, comfortable and the staff quite conversational"
United States
Diane
The price is AED 643
AED 697 total
includes taxes & fees
31 Jan - 1 Feb
Fairfield Inn & Suites by Marriott Keene Downtown

Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (556 reviews)
"So much love and thoughtfulness was put into our room and common area. Comfy beds, little touches like free snacks and goodies and super clean room. It's also super dog friendly! There's also a fantastic little coffee stand walking distance. "
United States
JILL
The price is AED 268
AED 524 total
includes taxes & fees
26 Jan - 27 Jan
Sleep Woodstock Motel

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very Good, (1,002 reviews)
"Great stay pool was very nice"
United States
Patrick
The price is AED 511
AED 554 total
includes taxes & fees
25 Jan - 26 Jan
Best Western Plus Keene Hotel

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa
4.5 star property
Manchester Village Historic District
7.4 out of 10, Good, (590 reviews)
"The resort really needs updating...."
United States
Elizabeth
The price is AED 486
AED 734 total
includes taxes & fees
1 Feb - 2 Feb
The Equinox Golf Resort & Spa
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.

Top Chester Hotel Reviews

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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 plenty of time to take in activities in the area like Okemo Mountain Resort and Stratton Mountain Resort.