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

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Check availability on Chester Family Hotels

Tonight
28 Sep - 29 Sep
Tomorrow
29 Sep - 30 Sep
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

Our top choices for Chester family-friendly hotels

Lobby sitting area
Interior
Mansion Suite (Room 12) | Bathroom | Free toiletries, hair dryer, towels
Exterior

1. The Hartness House

The Hartness House
Springfield
AED 759
AED 835 total
includes taxes & fees
25 Oct - 26 Oct
The Hartness House
Exterior
Dining
Coffee/tea maker, fridge, microwave, oven
2 bedrooms, iron/ironing board, WiFi (free), bed sheets

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.
AED 624
AED 1,279 total
includes taxes & fees
30 Sep - 1 Oct
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Lobby lounge
Exterior
Bar (on property)
Mountain view

3. 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.
AED 531
AED 585 total
includes taxes & fees
30 Sep - 1 Oct
Sun Lodge near Manchester VT, Ascend Collection Hotel
Children's play area - indoor
Exterior
Lobby sitting area
Lobby sitting area

4. Aerie Inn of Vermont

Aerie Inn of Vermont
East Dorset
  • Family fun awaits in the mountains with easy lake access, outdoor playground, and cozy firepit for evening entertainment.
AED 400
AED 436 total
includes taxes & fees
29 Sep - 30 Sep
Aerie Inn of Vermont
Front of property
Reception
Restaurant
30-inch flat-screen TV with digital channels, Netflix, Hulu

5. COHO Inn & Motor Lodge

COHO Inn & Motor Lodge
Weston
  • Adventure awaits at this family-friendly lodge where breakfast is included and Magic Mountain Ski Resort is just a short drive away.
AED 754
AED 822 total
includes taxes & fees
29 Sep - 30 Sep
COHO Inn & Motor Lodge
Arcade
Indoor spa tub
Reception
Reception

6. 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.
AED 490
AED 593 total
includes taxes & fees
30 Sep - 1 Oct
The Black Bear Lodge at Stratton Mountain Resort
Premier Quadruple Room, Garden View | Premium bedding, WiFi (free), individually decorated
Exterior
Sport court
Pub

7. The Landgrove

The Landgrove
Londonderry
AED 803
AED 875 total
includes taxes & fees
4 Oct - 5 Oct
The Landgrove
Property grounds
Exterior
Exterior
Interior detail

8. The Putney Inn

The Putney Inn
Putney
  • Fun family adventures await with easy beach access, cozy rooms, and thoughtful in-room amenities for all ages.
AED 309
AED 340 total
includes taxes & fees
25 Oct - 26 Oct
The Putney Inn
Billiards
Dinner served
Property amenity
Exterior

9. Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Brownsville
AED 584
AED 697 total
includes taxes & fees
26 Oct - 27 Oct
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Deluxe Suite | Private kitchen | Coffee/tea maker, mini-fridge, microwave, freezer
Electric vehicle charging station
Desk, blackout drapes, iron/ironing board, WiFi (free)
Exterior

10. Sleep Woodstock Motel

Sleep Woodstock Motel
Woodstock
  • Family-friendly motel offers fun by the river with firepit activities, cozy rooms, and easy access to outdoor adventures.
AED 331
AED 505 total
includes taxes & fees
27 Oct - 28 Oct
Sleep Woodstock Motel
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Choose what matters most at family-friendly hotels in Chester

Breakfast included
Pool
All-inclusive
4 stars
5 stars

Top Chester Hotel Reviews

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 Magic Mountain Ski Resort.