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

Chester Hotel Guide - Family Friendly Hotels in Chester, Vermont

  • 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 Friendly Hotels

Tonight
27 Aug - 28 Aug
Tomorrow
28 Aug - 29 Aug
This weekend
28 Aug - 30 Aug
Next weekend
4 Sept - 6 Sept

Our top choices for Chester family-friendly hotels

1. The Hartness House

The Hartness House
Springfield
€167
includes taxes & fees
30 Aug - 31 Aug
The Hartness House

2. Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Grafton
  • Renovated schoolhouse cabin offers tranquil family time with hiking trails and children's books.
€307
includes taxes & fees
7 Sept - 8 Sept
Charming Fully Renovated One-Room Schoolhouse on 22+ acres

3. Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Brownsville
€144
includes taxes & fees
30 Aug - 31 Aug
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

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.
€135
includes taxes & fees
1 Sept - 2 Sept
The Black Bear Lodge at Stratton Mountain Resort

5. Sun Lodge near Manchester VT, Ascend Collection Hotel

Sun Lodge near Manchester VT, Ascend Collection Hotel
Bromley Mountain
  • Family fun at this ski-in/ski-out lodge offers game room adventures, mountain access, and recently renovated spaces.
€120
includes taxes & fees
17 Sept - 18 Sept
Sun Lodge near Manchester VT, Ascend Collection Hotel

6. 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.
€123
includes taxes & fees
2 Sept - 3 Sept
Aerie Inn of Vermont

7. The Landgrove

The Landgrove
Londonderry
€167
includes taxes & fees
3 Sept - 4 Sept
The Landgrove

8. Okemo Mountain, Family Affordable 2 fl village walk to town, Dogs OK.fireplace.

Okemo Mountain, Family Affordable 2 fl village walk to town, Dogs OK.fireplace.
Ludlow
€223
includes taxes & fees
28 Aug - 29 Aug
Okemo Mountain, Family Affordable 2 fl village walk to town, Dogs OK.fireplace.

9. 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.
€103
includes taxes & fees
1 Sept - 2 Sept
The Putney Inn

10. Four Columns Inn

Four Columns Inn
Newfane
€146
includes taxes & fees
30 Aug - 31 Aug
Four Columns Inn
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

Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

10/10 Excellent
"Rooms were clean and comfortable ,staff was pleasant. Love the Manchester such a beautiful town."
Christina 2-night trip
Posted 2 hours ago
Kimpton Taconic Hotel by IHG
Hampton Inn Brattleboro

Hampton Inn Brattleboro

8/10 Good
"Very clean. Good full breakfast."
Barbara 1-night trip
Posted 21 hours ago
Hampton Inn Brattleboro
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

8/10 Good
"Clean room breakfast was good"
Lori 1-night trip
Posted 1 day ago
Best Western Plus Keene Hotel
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent
"It was good!"
Ingrid 4-night trip
Posted 2 days ago
Keene Elm City Hotel, an Ascend Collection Hotel
The Shire Woodstock

The Shire Woodstock

8/10 Good
"It was a nice and cozy place to stay and experience Woodstock VT."
Clayton 2-night trip
Posted 3 days ago
The Shire Woodstock
The Palmer House Resort, an Ascend Collection Hotel

The Palmer House Resort, an Ascend Collection Hotel

10/10 Excellent
"👍"
Chris 1-night trip
Posted 3 days ago
The Palmer House Resort, an Ascend Collection Hotel
Colonial Motel

Colonial Motel

8/10 Good
"X"
Steven 1-night trip
Posted 3 days ago
Colonial Motel
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

8/10 Good
"The place was clean and well maintained. Ample room and comfortable as well. Having a kitchen and having it properly equipped was a big plus."
Chris 2-night trip
Posted 5 days ago
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

10/10 Excellent
"We loved this hotel, really nice amenities, great rooms. I wish we had planned less activities and spent more time at the hotel. If you want to stay in the hotel, plan to spend a day in the hotel. Breakfast ends at 11 and bar closes at around 10 depending on crowd."
Gabriel 2-night trip
Posted 11 days ago
The Equinox Golf Resort & Spa

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.