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Top Winchester Family Hotels

Our top choices for Winchester family-friendly hotels

Best Western Plus Keene Hotel

3.0 star property
8.4 out of 10, Very Good, (1008)
"Great for stay"
The price is SAR 597
SAR 647 total
includes taxes & fees
1 Sep - 2 Sep
Best Western Plus Keene Hotel

Fairfield Inn & Suites by Marriott Keene Downtown

2.5 star property
8.8 out of 10, Excellent, (735)
"We stayed in the loft room and it was great! Right downtown, free parking right out the back and the staff is super nice. I would definitely go back!"
The price is SAR 668
SAR 725 total
includes taxes & fees
15 Sep - 16 Sep
Fairfield Inn & Suites by Marriott Keene Downtown

Colonial Motel And Spa

3.0 star property
6.8 out of 10, (1003)
"Always a pleasure to stay at the Colonial"
The price is SAR 454
SAR 499 total
includes taxes & fees
1 Sep - 2 Sep
Colonial Motel And Spa

Econo Lodge Brattleboro

2.0 star property
5.6 out of 10, (556)
"The good: convenient to grocery store next door. Linens were clean. The bad: room was dirty, had roaches, our feet were quickly filthy just from walking in the carpet, old liquid splashed on the walls and never cleaned. No housekeeping over three day stay."
The price is SAR 376
SAR 414 total
includes taxes & fees
29 Sep - 30 Sep
Econo Lodge Brattleboro

Family Friendly Hilltop House In Putney Vermont

9.4 out of 10, Exceptional, (56)
"The property was beautiful--great views, super peaceful, and fabulous hosts. "
The price is SAR 732
SAR 1,282 total
includes taxes & fees
13 Sep - 14 Sep
Family Friendly Hilltop House In Putney Vermont

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

10.0 out of 10, Exceptional, (7)
"Great, clean, charming cottage. The hosts are amazing and communicated every detail, very hospitable. Highly recommend. "
The price is SAR 832
SAR 1,016 total
includes taxes & fees
1 Sep - 2 Sep
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

Cobb Meadow House - Cozy 5 Bedroom New England home in The Monadnock Region

10.0 out of 10, Exceptional, (23)
"Good place to stay during a wedding week"
The price is SAR 1,653
SAR 2,786 total
includes taxes & fees
2 Sep - 3 Sep
Cobb Meadow House - Cozy 5 Bedroom New England home in The Monadnock Region

Entire Farmhouse with lots of open space 15 min north of Keene

10.0 out of 10, Exceptional, (37)
"Great location, great house, and wonderful breakfast. Would highly recommend and plan to stay there again some day soon."
The price is SAR 927
SAR 1,132 total
includes taxes & fees
2 Sep - 3 Sep
Entire Farmhouse with lots of open space 15 min north of Keene

FaLL Western Mass Getaway-Airhockey-Hot tub-Firepit

9.8 out of 10, Exceptional, (36)
"Great place and convenient to get to and from Berkshire East."
The price is SAR 1,062
SAR 2,402 total
includes taxes & fees
2 Sep - 3 Sep
FaLL Western Mass Getaway-Airhockey-Hot tub-Firepit
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.

Top Winchester Hotel Reviews

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