Family Hotels & Resorts in Chester from AU$145

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Our top choices for Chester family-friendly hotels

LUXE Forest Retreat

LUXE Forest Retreat
Chester
The price is AU$660
includes taxes & fees
28 Apr - 29 Apr
LUXE Forest Retreat

Historic 150-year-old farmhouse, Jacuzzi included

Historic 150-year-old farmhouse, Jacuzzi included
Chester Depot
9.8 out of 10, Exceptional, (16 reviews)
The price is AU$655
includes taxes & fees
28 Apr - 29 Apr
Historic 150-year-old farmhouse, Jacuzzi included

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (800 reviews)
The price is AU$192
includes taxes & fees
29 Apr - 30 Apr
Comfort Inn & Suites Brattleboro I-91

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very good, (1,006 reviews)
  • cleanliness
    Fun family adventures await with easy beach access, cosy rooms, and thoughtful in-room amenities for all ages.
The price is AU$145
includes taxes & fees
29 Apr - 30 Apr
The Putney Inn

Aerie Inn of Vermont

Aerie Inn of Vermont
2.0 star property
East Dorset
9.4 out of 10, Exceptional, (180 reviews)
  • cleanliness
    Family fun awaits in the mountains with easy lake access, outdoor playground, and cosy firepit for evening entertainment.
The price is AU$176
includes taxes & fees
28 Apr - 29 Apr
Aerie Inn of Vermont

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 AU$218
includes taxes & fees
28 Apr - 29 Apr
Best Western Plus Keene Hotel

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (33 reviews)
The price is AU$199
includes taxes & fees
29 Apr - 30 Apr
Four Columns Inn

Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (573 reviews)
  • cleanliness
    Family-friendly motel offers fun by the river with firepit activities, cosy rooms, and easy access to outdoor adventures.
The price is AU$168
includes taxes & fees
28 Apr - 29 Apr
Sleep Woodstock Motel

Stanford House

Stanford House
2.5 star property
Manchester Center
9.2 out of 10, Wonderful, (74 reviews)
The price is AU$153
includes taxes & fees
28 Apr - 29 Apr
Stanford House

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Grafton
9.6 out of 10, Exceptional, (169 reviews)
  • cleanliness
    Renovated schoolhouse cabin offers tranquil family time with hiking trails and children's books.
The price is AU$514
includes taxes & fees
28 Apr - 29 Apr
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
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.

Choose what matters most at family-friendly hotels in Chester

Top Chester Hotel Reviews

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.