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Check availability on Chester Family Hotels

Our top choices for Chester family-friendly hotels

LUXE Forest Retreat

LUXE Forest Retreat
Chester
The price is ¥47,474
¥75,282 total
includes taxes & fees
May 12 - May 13
LUXE Forest Retreat

Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (578 reviews)
  • cleanliness
    Family-friendly motel offers fun by the river with firepit activities, cozy rooms, and easy access to outdoor adventures.
"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
The price is ¥10,623
¥20,616 total
includes taxes & fees
May 14 - May 15
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.
"Very comfortable room and nice staff. Will stay there again. "
United States
Laura
The price is ¥18,097
¥19,726 total
includes taxes & fees
May 13 - May 14
Aerie Inn of Vermont

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (38 reviews)
"My stay was wonderful. Great accommodations, friendly and helpful staff, the pub downstairs was perfect to grab a quick bite and a drink. I will be staying again next time I am in the area"
United States
Glenn
The price is ¥20,447
¥22,287 total
includes taxes & fees
May 12 - May 13
Four Columns Inn

The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very Good, (1,005 reviews)
  • cleanliness
    Fun family adventures await with easy beach access, cozy rooms, and thoughtful in-room amenities for all ages.
"The room was what you would expect for this somewhat dated yet comfy, Inn. The price was reasonable. The staff was friendly. The Inn is pet friendly with a reasonable cost. You can tell that upgrades have been done. I think my only complaint would be the bath towels that were offered. It would be nice if they offered something a little larger and not so rough. The location is right off of the interstate which was very convenient. Overall it was a comfy, quiet little place that was reasonably...
United States
Robert
The price is ¥14,736
¥16,210 total
includes taxes & fees
May 13 - May 14
The Putney Inn

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (803 reviews)
"Convenient budget friendly for a family ski weekend"
United States
Danielle
The price is ¥22,327
¥24,559 total
includes taxes & fees
Jun 1 - Jun 2
Comfort Inn & Suites Brattleboro I-91

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very Good, (1,009 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.
"We frequently visit this hotel to visit my family in town."
United States
Allison
The price is ¥24,129
¥26,180 total
includes taxes & fees
May 12 - May 13
Best Western Plus Keene Hotel

Stanford House

Stanford House
2.5 star property
Manchester Center
9.2 out of 10, Wonderful, (74 reviews)
"Nice friendly accommodating "
United States
thomas
The price is ¥17,627
¥21,177 total
includes taxes & fees
May 12 - May 13
Stanford House

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, (992 reviews)
  • cleanliness
    Family escapes to Black Bear Lodge offer mountain adventure with convenient ski shuttles and a game room for kids.
"Very friendly staff, excellent location. Breakfast was great and room was just what we needed"
United States
Val
The price is ¥20,310
¥24,576 total
includes taxes & fees
May 12 - May 13
The Black Bear Lodge at Stratton Mountain Resort

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.
"This is our second stay here and the cabin will continue to be our first choice when visiting. The cabin is cozy with a good selection of board games and a well equipped kitchen. We also appreciate having a pet friendly place to stay. "
United States
Jennifer
The price is ¥26,636
¥55,979 total
includes taxes & fees
May 14 - May 15
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 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.