Find Family Hotels in Chester, VT
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check availability on Chester Family Hotels
Tonight
Aug 10 - Aug 11Tomorrow
Aug 11 - Aug 12This weekend
Aug 14 - Aug 16Next weekend
Aug 21 - Aug 23Our top choices for Chester family-friendly hotels
￥28,343
￥31,177 total
includes taxes & fees
Aug 18 - Aug 19
2. The Putney Inn
The Putney InnPutney
- Fun family adventures await with easy beach access, cozy rooms, and thoughtful in-room amenities for all ages.
￥19,523
￥21,475 total
includes taxes & fees
Aug 11 - Aug 12
￥20,872
￥22,958 total
includes taxes & fees
Aug 16 - Aug 17
4. Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Charming Fully Renovated One-Room Schoolhouse on 22+ acresGrafton
- Renovated schoolhouse cabin offers tranquil family time with hiking trails and children's books.
￥26,819
￥58,308 total
includes taxes & fees
Aug 11 - Aug 12
5. Colonial Motel
Colonial MotelBrattleboro
- Family fun abounds at this colonial motel with two indoor pools, spa services, and family dining options.
￥11,784
￥12,963 total
includes taxes & fees
Aug 11 - Aug 12
6. Best Western Plus Keene Hotel
Best Western Plus Keene HotelKeene
- A family vacation haven where kids splash in the indoor pool while parents relax—the perfect balance of fun and comfort at every age.
￥23,506
￥25,505 total
includes taxes & fees
Aug 19 - Aug 20
7. Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Holiday Inn Club Vacations Mount Ascutney Resort by IHGBrownsville
￥21,929
￥26,482 total
includes taxes & fees
Aug 11 - Aug 12
8. Four Winds Country Motel
Four Winds Country MotelManchester Center
- A serene family retreat with seasonal pool, playground, and spacious rooms perfect for creating lasting vacation memories.
￥24,528
￥26,980 total
includes taxes & fees
Sep 1 - Sep 2
View all properties
Top Chester Hotel Reviews
Latchis Hotel
8/10 Good
"In an old Theater building. Definitely has character and cool features. We arrived too late for the movies, but still fun. In central Brattleboro which has some interesting shops, but is suffering from homelessnes and mental illness/drug use. Didnt really feel unsafe and we walked a few blocks to a fun restaurant with good food & karioke. Person at desk was lovely and helpful. Room was ok- a little dated and could be cleaner."
Hampton Inn Brattleboro
10/10 Excellent
"Staff is very helpful"
Sleep Woodstock Motel
10/10 Excellent
"The property looks newly refurbished. Everything was in excellent shape, and the grounds were quite nice. And very clean. Also pet friendly. Would definitely recommend!"
Keene Elm City Hotel, an Ascend Collection Hotel
10/10 Excellent
"As always, this place never disappoints. From the friendly staff that greets you at check-in, to the breakfast buffet that gives you a good variety to start your day… this will always be my go-to when visiting Keene."
Colonial Motel
8/10 Good
"Kind personnel, large green area. Breakfast is too basic though."
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
10/10 Excellent
"Perfect"
Woodstock Inn & Resort
10/10 Excellent
"Amazing! Will visit again."
The Equinox Golf Resort & Spa
8/10 Good
"Good place to stay, but not great."
Kimpton Taconic Hotel by IHG
10/10 Excellent
"Excellent amenities and perfect if you're traveling with a dog to VT. Rooms are very nice albeit a bit small and very low water pressure in the shower."