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Compare 40 Cottages in Winchester with updated reviews, rates, and availability.
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
9.0 out of 10, Wonderful, (42)
Cottage on Partridge Pond
Cottage on Partridge Pond
10.0 out of 10, Exceptional, (16)
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
10.0 out of 10, Exceptional, (14)
VRBO Top 10 - Copley's Lakefront Cottage and Guest House on its own Peninsula
VRBO Top 10 - Copley's Lakefront Cottage and Guest House on its own Peninsula
10.0 out of 10, Exceptional, (4)
Waterfront Cottage on Scenic Sportsman Pond
Waterfront Cottage on Scenic Sportsman Pond
9.6 out of 10, Exceptional, (41)
Cottage on Laurel Lake, Private lake access, picture perfect sunsets
Cottage on Laurel Lake, Private lake access, picture perfect sunsets
9.4 out of 10, Exceptional, (3)
Vacationer's oasis on the waterfront of picturesque Pearly Pond.
Vacationer's oasis on the waterfront of picturesque Pearly Pond.
10.0 out of 10, Exceptional, (28)
Charming Jaffrey Cottage w/ Deck & Grill!
Charming Jaffrey Cottage w/ Deck & Grill!
10.0 out of 10, Exceptional, (39)
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.
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Other property types in Winchester
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
9.0 out of 10, Wonderful, (42)
Charming Waterfront Log Cabin
Charming Waterfront Log Cabin
9.4 out of 10, Exceptional, (36)
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT
10.0 out of 10, Exceptional, (48)
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.
Recent reviews of Winchester hotels
Recent reviews of Winchester hotels
5/5 Excellent
Great Stay!
"The service was top notch and all the extra touches made our stay special. Homemade cookies and the travel breakfast bags were amazing. The staff was professional, efficient and ever so kind. The hotel is under renovation, but we still had a wonderful stay. 5 stars"
A verified traveler stayed at Hampton Inn Brattleboro
Posted 19 hours ago