Family Hotels & Resorts in Chester

Start date: Check-in selected.
To Date
End date: Check-out

  • 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

Best Chester Family 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, (106)
"Room was super quiet and clean. "
United States
Ernest
The price is NZ$366
includes taxes & fees
24 Nov - 25 Nov
Stone Hearth Inn and Eatery
Interior
King & Queen Suite in Historic Inn Circa 1780

King & Queen Suite in Historic Inn Circa 1780

Chester Depot
9.8 out of 10, Exceptional, (16)
"The property has new owners and they clearly are working very hard to establish their business. The Inn was spotless, and they were very accommodating."
United States
Jean
The price is NZ$400
includes taxes & fees
16 Nov - 17 Nov
King & Queen Suite in Historic Inn Circa 1780
Interior
Whimsical Room & Private Bathroom in Historic Inn

Whimsical Room & Private Bathroom in Historic Inn

Chester Depot
8.8 out of 10, Excellent, (9)
"The room was really cozy and the community area was quaint and comfortable. "
United States
Bethany
The price is NZ$257
includes taxes & fees
16 Nov - 17 Nov
Whimsical Room & Private Bathroom in Historic Inn
1 bedroom, desk, iron/ironing board, free WiFi
Honeymoon Suite with Jacuzzi Tub in Historic Inn

Honeymoon Suite with Jacuzzi Tub in Historic Inn

Chester Depot
8.6 out of 10, Excellent, (7)
"We had a fantastic time staying in the Chester House. It was a short drive to Okemo Mountain, which was our main reason for booking, but the town of Chester, like the room we stayed in, was incredibly charming!"
United States
Jonathan G.
The price is NZ$315
includes taxes & fees
16 Nov - 17 Nov
Honeymoon Suite with Jacuzzi Tub in Historic Inn
Lobby
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

2.5 star property
Brattleboro
8.6 out of 10, Excellent, (728)
"Check in was easy and there is coffee available 24 hours a day!"
United States
Michelle
The price is NZ$203
includes taxes & fees
17 Nov - 18 Nov
Comfort Inn & Suites Brattleboro I-91
Exterior
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 star property
Manchester
7.4 out of 10, Good, (567)
"Nice old Inn!"
United States
Daniel
The price is NZ$308
includes taxes & fees
23 Nov - 24 Nov
The Equinox Golf Resort & Spa
Exterior
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, (853)
"The area around the Palmer House is so beautiful. Mountains everywhere!! "
United States
Mark
The price is NZ$226
includes taxes & fees
3 Dec - 4 Dec
The Palmer House Resort, an Ascend Collection Hotel
Premium bedding, individually decorated, individually furnished, desk
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

3.0 star property
Keene
8.4 out of 10, Very good, (1001)
"Hotel was great."
United States
Heidi
The price is NZ$286
includes taxes & fees
26 Nov - 27 Nov
Best Western Plus Keene Hotel
Sun deck
Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel

2.5 star property
West Chesterfield
9.6 out of 10, Exceptional, (626)
"Loved my stay"
United States
Christine
The price is NZ$292
includes taxes & fees
14 Dec - 15 Dec
Riverside Hotel, an Ascend Collection Hotel
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, (749)
"Lovely spotless well-appointed room. Kind and very helpful staff. Thank you!"
United States
Margaret
The price is NZ$353
includes taxes & fees
7 Dec - 8 Dec
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.
View all properties

Top Chester Hotel Reviews

Jackson Gore Village

Jackson Gore Village

10/10 Excellent
"Amazing trip! "
Tracey 3-night trip
Posted 3 days ago
Jackson Gore Village

Explore a world of travel with Expedia

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 Plummer's Sugar House.