Chester Hotel Guide - Family Friendly Hotels in Chester, Vermont

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Check availability on Chester Family Friendly Hotels

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 €264
includes taxes & fees
14 Jan - 15 Jan
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

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very good, (1,002 reviews)
"The room was okay for a quick stop to rest. "
United States
Janice
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, (758 reviews)
"The room was clean and the staff was wonderful"
United States
Julianne
The price is €117
includes taxes & fees
29 Jan - 30 Jan
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, (1,001 reviews)
"Great stay pool was very nice"
United States
Patrick
The price is €129
includes taxes & fees
21 Jan - 22 Jan
Best Western Plus Keene Hotel

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 €163
includes taxes & fees
19 Jan - 20 Jan
Fairfield Inn & Suites by Marriott Keene Downtown

Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (554 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 €123
includes taxes & fees
15 Jan - 16 Jan
Sleep Woodstock Motel

On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1,010 reviews)
"Brilliant stay"
United States
Enrico
The price is €255
includes taxes & fees
12 Feb - 13 Feb
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, (952 reviews)
"Every thing was excellent "
United States
James
The price is €192
includes taxes & fees
19 Jan - 20 Jan
The Black Bear Lodge at Stratton Mountain Resort

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, (877 reviews)
"Rooms were spotless and staff was great!"
United States
Helen
The price is €99
includes taxes & fees
27 Jan - 28 Jan
The Palmer House Resort, an Ascend Collection Hotel
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

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 Bonnie's Bundles Dolls and DaVallia Art & Accents. Make sure that you have plenty of time to take in activities in the area such as Okemo Mountain Resort and Stratton Mountain Resort.