Family Hotels & Resorts in Chester from NZ$224

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Chester Family Hotels

Our top choices for Chester family-friendly hotels

Front of property

Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
3.0 star property
Chester
9.2 out of 10, Wonderful, (112 reviews)
"So great all around!"
United States
Janet
The price is NZ$421
includes taxes & fees
13 Mar - 14 Mar
Stone Hearth Inn and Eatery
Interior

Historic 150-year-old farmhouse, Jacuzzi included

Historic 150-year-old farmhouse, Jacuzzi included
Chester Depot
9.8 out of 10, Exceptional, (14 reviews)
"Brought my mom here for leaf peeping. The Farmhouse was clean, comfortable and very inviting. Plenty to do in the surrounding area. Soaking in the hot tub & stargazing in the evening was wonderful! Owner was easy to communicate with. Would highly recommend!"
United States
Michele B.
The price is NZ$808
includes taxes & fees
11 Feb - 12 Feb
Historic 150-year-old farmhouse, Jacuzzi included
Lobby

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (760 reviews)
"The room was clean and the staff was wonderful"
United States
Julianne
The price is NZ$224
includes taxes & fees
5 Mar - 6 Mar
Comfort Inn & Suites Brattleboro I-91
Deluxe Suite | Private kitchen

Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (557 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 NZ$236
includes taxes & fees
9 Mar - 10 Mar
Sleep Woodstock Motel
Children’s activities

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa
4.5 star property
Manchester Village Historic District
7.4 out of 10, Good, (594 reviews)
"We have been staying at the Equinox for over 35 yrs. Love the whole scene and vibe. Love the pool and hot tub. Love the big real wood fireplace. "
United States
Patricia
The price is NZ$316
includes taxes & fees
23 Feb - 24 Feb
The Equinox Golf Resort & Spa
Exterior

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, (762 reviews)
"Everything was clean, comfortable and the staff quite conversational"
United States
Diane
The price is NZ$314
includes taxes & fees
25 Feb - 26 Feb
Fairfield Inn & Suites by Marriott Keene Downtown
Land view from property

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.6 out of 10, Exceptional, (20 reviews)
"Everything was great 👍 I will stay there again and highly recommend to others "
United States
Linda
Four Columns Inn
Children’s activities

On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1,006 reviews)
"Everything was amazing from the room to the pool to the restaurant and staff. "
United States
Ilana
The price is NZ$491
includes taxes & fees
16 Feb - 17 Feb
On The River Inn
Property grounds

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very good, (1,003 reviews)
"perfect room, very clean and friendly staff"
Canada
Marc-André
The Putney Inn
Restaurant

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)
"Great stay pool was very nice"
United States
Patrick
The price is NZ$249
includes taxes & fees
11 Feb - 12 Feb
Best Western Plus Keene 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.
View all properties

Choose what matters most at family-friendly hotels in Chester

Breakfast included
Pool

Top Chester Hotel Reviews

The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort

10/10 Excellent
"Accommodating staff"
Robert 1-night trip
Posted 6 days ago
The Black Bear Lodge at Stratton Mountain Resort

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.