Find Family Hotels in Chester, VT

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Check availability on Chester Family Hotels

Top Chester Family Hotels

Stone Hearth Inn and Eatery

3.0 star property
Chester
9.2 out of 10, Wonderful, (106)
"Good breakfast and dinner options. Great location for hiking."
United States
Paul
The price is AED 683
AED 744 total
includes taxes & fees
20 Nov - 21 Nov
Stone Hearth Inn and Eatery

King & Queen Suite in Historic Inn Circa 1780

Chester Depot
9.8 out of 10, Exceptional, (16)
"Central for our needs. easy check in process. Lovely large room with comfy beds. "
United States
HIlary H.
The price is AED 1,025
AED 1,485 total
includes taxes & fees
3 Dec - 4 Dec
King & Queen Suite in Historic Inn Circa 1780

Whimsical Room & Private Bathroom in Historic Inn

Chester Depot
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!"
United States
Paul S.
The price is AED 364
AED 613 total
includes taxes & fees
23 Nov - 24 Nov
Whimsical Room & Private Bathroom in Historic Inn

Honeymoon Suite with Jacuzzi Tub in Historic Inn

Chester Depot
8.6 out of 10, Excellent, (7)
"Charming place, hope to go back soon."
United States
Sharon S.
The price is AED 514
AED 798 total
includes taxes & fees
30 Nov - 1 Dec
Honeymoon Suite with Jacuzzi Tub in Historic Inn

Comfort Inn & Suites Brattleboro I-91

2.5 star property
Brattleboro
8.6 out of 10, Excellent, (728)
"Absolutely perfect stay for a business trip"
United States
Lyndsey
The price is AED 405
AED 445 total
includes taxes & fees
7 Dec - 8 Dec
Comfort Inn & Suites Brattleboro I-91

The Equinox Golf Resort & Spa

4.5 star property
Manchester
7.4 out of 10, Good, (568)
"Nice old Inn!"
United States
Daniel
The price is AED 383
AED 616 total
includes taxes & fees
20 Nov - 21 Nov
The Equinox Golf Resort & Spa

Sleep Woodstock Motel

2.0 star property
Woodstock
9.6 out of 10, Exceptional, (542)
"Clean, friendly, easy check in, welcoming accommodations. Can’t wait to come back"
United States
David
The price is AED 304
AED 496 total
includes taxes & fees
20 Nov - 21 Nov
Sleep Woodstock Motel

The Putney Inn

2.5 star property
Putney
8.4 out of 10, Very Good, (1000)
"The Putney Inn is a great place to stay!! The people who work there are very nice and the location is great!"
United States
Kristen
The Putney Inn

Best Western Plus Keene Hotel

3.0 star property
Keene
8.4 out of 10, Very Good, (1001)
"Great staff, clean room, nice breakfast"
United States
DORTHY
The price is AED 511
AED 554 total
includes taxes & fees
23 Nov - 24 Nov
Best Western Plus Keene Hotel

Four Columns Inn

4.0 star property
Newfane
9.8 out of 10, Exceptional, (12)
"Cozy inn in a beautiful setting, and great staff and service"
United States
Archith
The price is AED 479
AED 522 total
includes taxes & fees
20 Nov - 21 Nov
Four Columns Inn
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

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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 Bonnie's Bundles Dolls and DaVallia Art & Accents. Make sure you have lots of time for activities like Vermont Country Store and Plummer's Sugar House.