Find Family Hotels in Chester, VT

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Check availability on Chester Family Hotels

Tonight
5 Oct - 6 Oct
Tomorrow
6 Oct - 7 Oct
Next weekend
10 Oct - 12 Oct
In two weeks
17 Oct - 19 Oct

Top Chester Family Hotels

The Putney Inn
Property grounds

The Putney Inn

2.5 star property
8.4 out of 10, Very Good, (1001)
"Very enjoyable stay"
The Putney Inn
Riverside Hotel, an Ascend Collection Hotel
Sundeck

Riverside Hotel, an Ascend Collection Hotel

2.5 star property
9.6 out of 10, Exceptional, (606)
"The hotel is on a beautiful river front and the grounds are lovely. We drove to find dinner and it was easy enough. The hotel has a wonderful, helpful staff. "
The price is AED 559
AED 606 total
includes taxes & fees
27 Oct - 28 Oct
Riverside Hotel, an Ascend Collection Hotel
Stanford House
Outdoor dining

Stanford House

2.5 star property
9.0 out of 10, Wonderful, (61)
"good basic bed for traveling "
The price is AED 461
AED 554 total
includes taxes & fees
1 Nov - 2 Nov
Stanford House
Stone Hearth Inn and Eatery
Front of property

Stone Hearth Inn and Eatery

3.0 star property
9.2 out of 10, Wonderful, (96)
"Sweet place to stay"
The price is AED 994
AED 1,084 total
includes taxes & fees
6 Oct - 7 Oct
Stone Hearth Inn and Eatery
Honeymoon Suite with Jacuzzi Tub in Historic Inn
1 bedroom, desk, iron/ironing board, free WiFi

Honeymoon Suite with Jacuzzi Tub in Historic Inn

8.6 out of 10, Excellent, (7)
"Charming place, hope to go back soon."
The price is AED 584
AED 884 total
includes taxes & fees
6 Oct - 7 Oct
Honeymoon Suite with Jacuzzi Tub in Historic Inn
Whimsical Room & Private Bathroom in Historic Inn
Interior

Whimsical Room & Private Bathroom in Historic Inn

8.8 out of 10, Excellent, (9)
"After a long month of work I needed a weekend in VT to calm the nerves. This was a beautiful spot to be in, glad I was here!"
The price is AED 547
AED 839 total
includes taxes & fees
15 Oct - 16 Oct
Whimsical Room & Private Bathroom in Historic Inn
King & Queen Suite in Historic Inn Circa 1780
Interior

King & Queen Suite in Historic Inn Circa 1780

9.8 out of 10, Exceptional, (16)
"The check in process was easy, and the space was beautiful. Great location for a weekend of skiing!"
The price is AED 841
AED 1,251 total
includes taxes & fees
6 Oct - 7 Oct
King & Queen Suite in Historic Inn Circa 1780
Best Western Plus Keene Hotel
Premium bedding, individually decorated, individually furnished, desk

Best Western Plus Keene Hotel

3.0 star property
8.4 out of 10, Very Good, (1006)
"Would definitely stay again. Very convenient location "
The price is AED 514
AED 558 total
includes taxes & fees
3 Nov - 4 Nov
Best Western Plus Keene Hotel
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Interior

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3.0 star property
9.0 out of 10, Wonderful, (757)
"It is Good place to stay. We enjoyed our stay here."
The price is AED 621
AED 727 total
includes taxes & fees
2 Nov - 3 Nov
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
The Hartness House
Interior

The Hartness House

3.0 star property
8.2 out of 10, Very Good, (320)
"Very nice property, stately, yet inviting. "
The price is AED 598
AED 652 total
includes taxes & fees
1 Nov - 2 Nov
The Hartness House
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

The Shire Woodstock

The Shire Woodstock

10/10 Excellent
"Great self free parking Amazing view of the river Cute grounds by the river "
Danuta 4-night trip
Posted 1 day ago
The Shire Woodstock

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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 lots of time for activities like Vermont Country Store and Plummer's Sugar House.