Family Hotels & Resorts in Chester from AU$219

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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, (107)
"Good breakfast and dinner options. Great location for hiking."
United States
Paul
The price is AU$320
includes taxes & fees
16 Dec - 17 Dec
Stone Hearth Inn and Eatery
Interior
Whimsical Room & Private Bathroom in Historic Inn

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 AU$309
includes taxes & fees
11 Dec - 12 Dec
Whimsical Room & Private Bathroom in Historic Inn
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)
"Central for our needs. easy check in process. Lovely large room with comfy beds. "
United States
HIlary H.
The price is AU$580
includes taxes & fees
3 Jan - 4 Jan 2026
King & Queen Suite in Historic Inn Circa 1780
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)
"Charming place, hope to go back soon."
United States
Sharon S.
The price is AU$520
includes taxes & fees
14 Dec - 15 Dec
Honeymoon Suite with Jacuzzi Tub in Historic Inn
Children’s activities
On The River Inn

On The River Inn

4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1000)
"This place was charming!! Enjoyed everything about it and so much to do right there in the inn."
United States
Ross
The price is AU$376
includes taxes & fees
22 Dec - 23 Dec
On The River 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, (737)
"Staff was friendly and pool was nice"
United States
Joshua
The price is AU$219
includes taxes & fees
22 Dec - 23 Dec
Comfort Inn & Suites Brattleboro I-91
Deluxe Suite
Sleep Woodstock Motel

Sleep Woodstock Motel

2.0 star property
Woodstock
9.6 out of 10, Exceptional, (548)
"The staff at this motel are 5 star! Lisa went above and beyond to make my stay easy since I was there for a medical procedure. "
United States
Crystal
The price is AU$247
includes taxes & fees
10 Dec - 11 Dec
Sleep Woodstock Motel
Garden
Four Columns Inn

Four Columns Inn

4.0 star property
Newfane
9.8 out of 10, Exceptional, (14)
"Cozy inn in a beautiful setting, and great staff and service"
United States
Archith
Four Columns Inn
Property grounds
The Putney Inn

The Putney Inn

2.5 star property
Putney
8.4 out of 10, Very good, (1003)
"Nice motel. "
United States
Richard
The Putney Inn
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, (1000)
"Great staff, clean room, nice breakfast"
United States
DORTHY
The price is AU$227
includes taxes & fees
10 Dec - 11 Dec
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.
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Top Chester Hotel Reviews

The Palmer House Resort, an Ascend Collection Hotel

The Palmer House Resort, an Ascend Collection Hotel

10/10 Excellent
"Nice staff, big room, comfortable bed, walking distance to downtown-overall great stay! "
Amanda 1-night trip
Posted 1 day ago
The Palmer House Resort, an Ascend Collection Hotel

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.