A covered wooden bridge over a river, surrounded by rocky terrain and greenery.

Chester Family Hotel

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Check availability on Chester Family Hotel

Tonight
9 Aug - 10 Aug
Tomorrow
10 Aug - 11 Aug
Next weekend
14 Aug - 16 Aug
In two weeks
21 Aug - 23 Aug

Our top choices for Chester family-friendly hotels

1. The Hartness House

The Hartness House
Springfield
HK$1,525
HK$1,677 total
includes taxes & fees
10 Aug - 11 Aug
The Hartness House

2. Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Brownsville
HK$1,090
HK$1,317 total
includes taxes & fees
10 Aug - 11 Aug
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3. Sun Lodge, an Ascend Collection Hotel

Sun Lodge, an Ascend Collection Hotel
Bromley Mountain
  • Family fun at this ski-in/ski-out lodge offers game room adventures, mountain access, and recently renovated spaces.
HK$998
HK$1,098 total
includes taxes & fees
30 Aug - 31 Aug
Sun Lodge, an Ascend Collection Hotel

4. The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort
Stratton
  • Family escapes to Black Bear Lodge offer mountain adventure with convenient ski shuttles and a game room for kids.
HK$1,024
HK$1,239 total
includes taxes & fees
1 Sept - 2 Sept
The Black Bear Lodge at Stratton Mountain Resort

5. The Landgrove

The Landgrove
Londonderry
HK$1,404
HK$1,702 total
includes taxes & fees
10 Aug - 11 Aug
The Landgrove

6. The Putney Inn

The Putney Inn
Putney
  • Fun family adventures await with easy beach access, cosy rooms, and thoughtful in-room amenities for all ages.
HK$971
HK$1,068 total
includes taxes & fees
10 Aug - 11 Aug
The Putney Inn

7. Aerie Inn of Vermont

Aerie Inn of Vermont
East Dorset
  • Family fun awaits in the mountains with easy lake access, outdoor playground, and cosy firepit for evening entertainment.
HK$1,036
HK$1,129 total
includes taxes & fees
10 Aug - 11 Aug
Aerie Inn of Vermont

8. Four Columns Inn

Four Columns Inn
Newfane
HK$1,229
HK$1,339 total
includes taxes & fees
10 Aug - 11 Aug
Four Columns Inn

9. Colonial Motel

Colonial Motel
Brattleboro
  • Family fun abounds at this colonial motel with two indoor pools, spa services, and family dining options.
HK$586
HK$645 total
includes taxes & fees
10 Aug - 11 Aug
Colonial Motel

10. Seesaw's Lodge

Seesaw's Lodge
Peru
  • Family adventures await with rustic elegance at this mountain lodge featuring playrooms, babysitting, and outdoor fun for all ages.
HK$1,593
HK$1,737 total
includes taxes & fees
16 Aug - 17 Aug
Seesaw's Lodge
View all properties

Choose what matters most at family-friendly hotels in Chester

Breakfast included
Pool
All-inclusive
4 stars
5 stars

Top Chester Hotel Reviews

Hampton Inn Brattleboro

Hampton Inn Brattleboro

10/10 Excellent
"Nice, new feeling hotel. Great room, spacious and updated. Hot hot tub and warm pool. Good breakfast with lots of options."
Danielle 1-night trip
Posted 3 hours ago
Hampton Inn Brattleboro
Sleep Woodstock Motel

Sleep Woodstock Motel

10/10 Excellent
"The property looks newly refurbished. Everything was in excellent shape, and the grounds were quite nice. And very clean. Also pet friendly. Would definitely recommend!"
Wayne 1-night trip
Posted 4 hours ago
Sleep Woodstock Motel
Latchis Hotel

Latchis Hotel

10/10 Excellent
"Excellent stay if you appreciate character and decor."
Ava 2-night trip
Posted 12 hours ago
Latchis Hotel
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent
"As always, this place never disappoints. From the friendly staff that greets you at check-in, to the breakfast buffet that gives you a good variety to start your day… this will always be my go-to when visiting Keene."
Patrick 1-night trip
Posted 12 hours ago
Keene Elm City Hotel, an Ascend Collection Hotel
Colonial Motel

Colonial Motel

8/10 Good
"Kind personnel, large green area. Breakfast is too basic though."
Alex 2-night trip
Posted 16 hours ago
Colonial Motel
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

10/10 Excellent
"Perfect"
zhuang 4-night trip
Posted 1 day ago
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Woodstock Inn & Resort

Woodstock Inn & Resort

10/10 Excellent
"Amazing! Will visit again."
Leah 4-night trip
Posted 1 day ago
Woodstock Inn & Resort
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

8/10 Good
"Good place to stay, but not great."
Sean 2-night trip
Posted 4 days ago
The Equinox Golf Resort & Spa
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

10/10 Excellent
"Excellent amenities and perfect if you're traveling with a dog to VT. Rooms are very nice albeit a bit small and very low water pressure in the shower."
Yvette 1-night trip
Posted 6 days ago
Kimpton Taconic Hotel by IHG

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.

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