Find Family Hotels in Chester, VT
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21 Aug - 23 AugOur top choices for Chester family-friendly hotels
AED 651
AED 716 total
includes taxes & fees
18 Aug - 19 Aug
2. 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.
AED 624
AED 1,362 total
includes taxes & fees
17 Aug - 18 Aug
3. Sun Lodge, an Ascend Collection Hotel
Sun Lodge, an Ascend Collection HotelBromley Mountain
- Family fun at this ski-in/ski-out lodge offers game room adventures, mountain access, and recently renovated spaces.
AED 467
AED 514 total
includes taxes & fees
3 Sep - 4 Sep
4. Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Holiday Inn Club Vacations Mount Ascutney Resort by IHGBrownsville
AED 511
AED 617 total
includes taxes & fees
17 Aug - 18 Aug
5. The Black Bear Lodge at Stratton Mountain Resort
The Black Bear Lodge at Stratton Mountain ResortStratton
- Family escapes to Black Bear Lodge offer mountain adventure with convenient ski shuttles and a game room for kids.
AED 451
AED 545 total
includes taxes & fees
1 Sep - 2 Sep
AED 739
AED 885 total
includes taxes & fees
3 Sep - 4 Sep
7. Seesaw's Lodge
Seesaw's LodgePeru
- Family adventures await with rustic elegance at this mountain lodge featuring playrooms, babysitting, and outdoor fun for all ages.
AED 746
AED 813 total
includes taxes & fees
16 Aug - 17 Aug
8. Aerie Inn of Vermont
Aerie Inn of VermontEast Dorset
- Family fun awaits in the mountains with easy lake access, outdoor playground, and cozy firepit for evening entertainment.
AED 485
AED 528 total
includes taxes & fees
17 Aug - 18 Aug
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Top Chester Hotel Reviews
Hampton Inn Brattleboro
10/10 Excellent
"Too tired to think about it. Sorry."
The Shire Woodstock
8/10 Good
"The staff was helpful. The room was clean. There was some 1st floor construction that it would have been nice to know about prior to check in. It didn’t impact our stay but made things a bit dusty. Very conveniently located to downtown area."
Best Western Plus Keene Hotel
10/10 Excellent
"The room was clean and quiet and the air conditioning worked well. There is a full breakfast and a nice work out room. This is the second time I have stayed at this Best Western, and I will stay there again the next time I am in Keane NH."
On The River Inn
10/10 Excellent
"Everything was good I cannot complain"
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."
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."