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

Family Hotels & Resorts in Chester from NZ$152

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Check availability on Chester Family Hotels

Next weekend
3 Jul - 5 Jul
In two weeks
10 Jul - 12 Jul

Our top choices for Chester family-friendly hotels

Lobby

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (821 reviews)
The price is NZ$220
includes taxes & fees
2 July - 3 July
Comfort Inn & Suites Brattleboro I-91
Premier Quadruple Room, Garden View

The Landgrove

The Landgrove
3.5 star property
Londonderry
The price is NZ$308
includes taxes & fees
28 June - 29 June
The Landgrove
Restaurant

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very good, (1,005 reviews)
  • cleanliness
    A family holiday haven where kids splash in the indoor pool while parents relax—the perfect balance of fun and comfort at every age.
The price is NZ$244
includes taxes & fees
9 July - 10 July
Best Western Plus Keene Hotel
Deluxe Suite

Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (586 reviews)
  • cleanliness
    Family-friendly motel offers fun by the river with firepit activities, cosy rooms, and easy access to outdoor adventures.
The price is NZ$222
includes taxes & fees
19 July - 20 July
Sleep Woodstock Motel
Dinner served

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (43 reviews)
The price is NZ$237
includes taxes & fees
29 June - 30 June
Four Columns Inn
Property grounds

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.6 out of 10, Excellent, (1,000 reviews)
  • cleanliness
    Fun family adventures await with easy beach access, cosy rooms, and thoughtful in-room amenities for all ages.
The price is NZ$212
includes taxes & fees
29 June - 30 June
The Putney Inn
Children’s play area – indoor

Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow
3.0 star property
West Dover
8.8 out of 10, Excellent, (109 reviews)
The price is NZ$152
includes taxes & fees
30 June - 1 July
Hideaway Inn Mt. Snow
Children’s play area – indoor

Aerie Inn of Vermont

Aerie Inn of Vermont
2.0 star property
East Dorset
9.4 out of 10, Exceptional, (182 reviews)
  • cleanliness
    Family fun awaits in the mountains with easy lake access, outdoor playground, and cosy firepit for evening entertainment.
The price is NZ$255
includes taxes & fees
28 June - 29 June
Aerie Inn of Vermont
Blackout curtains, free WiFi, bed sheets

Travelodge by Wyndham Brattleboro VT

Travelodge by Wyndham Brattleboro VT
2.5 star property
Brattleboro
6.0 out of 10, (780 reviews)
The price is NZ$153
includes taxes & fees
1 July - 2 July
Travelodge by Wyndham Brattleboro VT
Arcade

The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort
3.0 star property
Stratton
7.6 out of 10, Good, (998 reviews)
  • cleanliness
    Family escapes to Black Bear Lodge offer mountain adventure with convenient ski shuttles and a game room for kids.
The price is NZ$282
includes taxes & fees
9 July - 10 July
The Black Bear Lodge at Stratton Mountain Resort
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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Choose what matters most at family-friendly hotels in Chester

Breakfast included
Pool

Top Chester Hotel Reviews

Hampton Inn Brattleboro

Hampton Inn Brattleboro

10/10 Excellent
"The staff were very professional. Hotel was clean and very nice"
Lauren 2-night trip
Posted 8 hours ago
Hampton Inn Brattleboro

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.