Family Hotels & Resorts in Chester from NZ$136

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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)
"Great stay! Very cozy and homey. Very yummy breakfast! "
United States
Olena
The price is NZ$344
includes taxes & fees
13 Apr - 14 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)
"Clean large house, as described. Great hot tub and responsive host! "
United States
Lee F.
The price is NZ$745
includes taxes & fees
30 Mar - 31 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)
"A great place to stay with pets. Rooms are a little tight, but they are clean and comfortable."
United States
Ron
The price is NZ$208
includes taxes & fees
29 Mar - 30 Mar
Sleep Woodstock Motel

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very good, (1,002 reviews)
"Great Stay!"
United States
Nicholas
The price is NZ$153
includes taxes & fees
1 Apr - 2 Apr
The Putney Inn

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (26 reviews)
"Beautiful location and nice staff."
United States
Cynthia
The price is NZ$220
includes taxes & fees
1 Apr - 2 Apr
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, (786 reviews)
"The room was clean and the staff was wonderful"
United States
Julianne
The price is NZ$270
includes taxes & fees
31 Mar - 1 Apr
Comfort Inn & Suites Brattleboro I-91

On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1,000 reviews)
"Had a lovely stay while visiting, enjoyed the breakfast and the staff were all very friendly and accommodating. Would def stay here again"
United States
dylan
The price is NZ$331
includes taxes & fees
21 Apr - 22 Apr
On The River Inn

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)
"Nice rooms"
United States
Kim
The price is NZ$281
includes taxes & fees
29 Mar - 30 Mar
Best Western Plus Keene Hotel

Aerie Inn of Vermont

Aerie Inn of Vermont
2.0 star property
East Dorset
9.4 out of 10, Exceptional, (180 reviews)
"We enjoyed the quiet and the views."
United States
Michael
The price is NZ$218
includes taxes & fees
6 Apr - 7 Apr
Aerie Inn of Vermont

Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown
3.0 star property
Keene
8.8 out of 10, Excellent, (766 reviews)
"Everything was clean and the staff was friendly. "
United States
Kimberly
The price is NZ$329
includes taxes & fees
3 Apr - 4 Apr
Fairfield Inn & Suites by Marriott Keene Downtown
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 Vermont Country Store and Magic Mountain Ski Resort.