Family Hotels & Resorts in Chester from AU$170

  • 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

Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
3.0 star property
Chester
9.2 out of 10, Wonderful, (115 reviews)
"So great all around!"
United States
Janet
The price is AU$280
includes taxes & fees
24 Mar - 25 Mar
Stone Hearth Inn and Eatery

Historic 150-year-old farmhouse, Jacuzzi included

Historic 150-year-old farmhouse, Jacuzzi included
Chester Depot
9.8 out of 10, Exceptional, (14 reviews)
"Clean large house, as described. Great hot tub and responsive host! "
United States
Lee F.
The price is AU$695
includes taxes & fees
24 Mar - 25 Mar
Historic 150-year-old farmhouse, Jacuzzi included

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very good, (1,002 reviews)
"Great stay pool was very nice"
United States
Patrick
The price is AU$183
includes taxes & fees
15 Mar - 16 Mar
Best Western Plus Keene Hotel

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (781 reviews)
"The room was clean and the staff was wonderful"
United States
Julianne
The price is AU$175
includes taxes & fees
15 Mar - 16 Mar
Comfort Inn & Suites Brattleboro I-91

Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (559 reviews)
"So much love and thoughtfulness was put into our room and common area. Comfy beds, little touches like free snacks and goodies and super clean room. It's also super dog friendly! There's also a fantastic little coffee stand walking distance. "
United States
JILL
Sleep Woodstock Motel

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (24 reviews)
"Everything was great 👍 I will stay there again and highly recommend to others "
United States
Linda
Four Columns Inn

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very good, (1,009 reviews)
"perfect room, very clean and friendly staff"
Canada
Marc-André
The Putney Inn

Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow
2.0 star property
West Dover
8.8 out of 10, Excellent, (68 reviews)
"Clean cozy rooms, overall good stay"
United States
Wade
The price is AU$210
includes taxes & fees
15 Mar - 16 Mar
Hideaway Inn Mt. Snow

Four Winds Country Motel

Four Winds Country Motel
2.0 star property
Manchester Center
8.4 out of 10, Very good, (539 reviews)
"Place and owners are awful"
United States
brian
The price is AU$170
includes taxes & fees
12 Mar - 13 Mar
Four Winds Country Motel

Fairfield Inn & Suites by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown
3.0 star property
Keene
8.8 out of 10, Excellent, (766 reviews)
"Everything was clean, comfortable and the staff quite conversational"
United States
Diane
The price is AU$268
includes taxes & fees
18 Mar - 19 Mar
Fairfield Inn & Suites by Marriott Keene Downtown
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

The Annual Holiday Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.

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.