Find Family Hotels in Chester, VT from CA $142

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check availability on Chester Family Hotels

Our top choices for Chester family-friendly hotels

LUXE Forest Retreat

LUXE Forest Retreat
Chester
The price is CA $415
CA $656 total
includes taxes & fees
May 30 - May 31
LUXE Forest Retreat

Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (579 reviews)
  • cleanliness
    Family-friendly motel offers fun by the river with firepit activities, cozy rooms, and easy access to outdoor adventures.
The price is CA $102
CA $160 total
includes taxes & fees
May 17 - May 18
Sleep Woodstock Motel

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 cozy firepit for evening entertainment.
The price is CA $158
CA $173 total
includes taxes & fees
May 17 - May 18
Aerie Inn of Vermont

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very good, (1,000 reviews)
  • cleanliness
    Fun family adventures await with easy beach access, cozy rooms, and thoughtful in-room amenities for all ages.
The price is CA $129
CA $142 total
includes taxes & fees
May 18 - May 19
The Putney Inn

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (38 reviews)
The price is CA $177
CA $193 total
includes taxes & fees
May 25 - May 26
Four Columns Inn

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very good, (1,001 reviews)
  • cleanliness
    A family vacation haven where kids splash in the indoor pool while parents relax—the perfect balance of fun and comfort at every age.
The price is CA $211
CA $229 total
includes taxes & fees
May 17 - May 18
Best Western Plus Keene Hotel

Stanford House

Stanford House
2.5 star property
Manchester Center
9.2 out of 10, Wonderful, (74 reviews)
The price is CA $136
CA $164 total
includes taxes & fees
Jun 8 - Jun 9
Stanford House

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (804 reviews)
The price is CA $195
CA $215 total
includes taxes & fees
Jun 1 - Jun 2
Comfort Inn & Suites Brattleboro I-91

On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1,006 reviews)
  • cleanliness
    Riverside fun awaits families at this Woodstock retreat where kids enjoy the children's pool, playground, and arcade games.
The price is CA $1,369
CA $1,556 total
includes taxes & fees
May 16 - May 17
On The River Inn

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, (993 reviews)
  • cleanliness
    Family escapes to Black Bear Lodge offer mountain adventure with convenient ski shuttles and a game room for kids.
The price is CA $184
CA $222 total
includes taxes & fees
Jun 9 - Jun 10
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.

Choose what matters most at family-friendly hotels in Chester

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 DaVallia Art & Accents and Bonnie's Bundles Dolls. Make sure you have lots of time for activities like Vermont Country Store and Magic Mountain Ski Resort.