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Vacation rentals in Winchester

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Top-rated vacation rentals in Winchester

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest suite in Winchester
Suite 1 - Stay at a craft brewery - Winchester NH
Rent our one-bedroom private suite at The Outlaw Brewing Company. Onsite taproom to sample our small batch craft beer, hard cider, hard seltzer, and NEW craft cocktails! Several brews are only available here! Dog-friendly space. Pet dishes, toys, treats and even a crate can be provided if needed. You just bring your four-legged friend/s and their food over for a fun getaway at a unique location. Two-night minimum stay, no security deposit, no extra people charge, no additional cleaning fee.
$160 per night
Guest suite in Brattleboro
Charming studio in renovated 19th century church.
This spacious studio apartment is located in the former Swedish Congregational Church in historic Swedeville, a secluded hilly neighborhood built by Swedish immigrants in the 1800's. For years it housed Rick and Liza’s stained glass studio, which they have now lovingly and creatively transformed into a residence. The rental is minutes from the interstate and one mile from downtown Brattleboro, but the neighborhood has a rural and somewhat European flavor to it. COMING NEW KITCHEN PHOTO!
$90 per night
Apartment in Winchester
Downtown Loft above Winery and Distillery
Enjoy a lovely weekend getaway in this cute 1 bedroom loft, centrally located in Winchester, NH. Enjoy a tasting at New England Sweetwater Farm & Distillery next door and a pint on us at Outlaw Brewing Company. This cozy loft features a full kitchen, 3/4 bath as well as a bedroom and living room. 20 minutes to Keene, Brattleboro and Chesterfield. Access to Pisgah State Park, the Ahsuelot Rail Trail and Forest Lake. Come see what our beautiful area has to offer!
$69 per night

Stay near Winchester's top sights

Monadnock Speedway4 locals recommend
The Rustic Table8 locals recommend
Northfield Drive-In Theatre13 locals recommend
A1 Pizza of Winchester5 locals recommend
Kulick's Market7 locals recommend
Win Win Express3 locals recommend

Other great vacation rentals in Winchester

Apartment in Keene
"Up Top" Downtown Rooftop Apartment
$97 per night
Guest suite in Fitzwilliam
The Great Room in Historic Fitzwilliam
$95 per night
Bungalow in Brattleboro
Healix Luxury Getaway
$132 per night
Condo in Brattleboro
Private & Quiet Studio Apt. in Vermont
$79 per night
Guesthouse in Brattleboro
Light Filled Loft in the Vermont Countryside
$125 per night
Cabin in Guilford
Serenity Now - Couples Retreat or Writer's Dream
$169 per night
Apartment in Dummerston
HeART Barn Retreat
$76 per night
Cottage in Orange
The Lake Cottage: A Sweetwater Stay
$102 per night
Guesthouse in Putney
Cozy cottage loft and retreat
$100 per night
Apartment in Shelburne Falls
In town, newly renovated studio with private deck
$95 per night
Apartment in Brattleboro
Contemporary forest eco-retreat, mountain views
$121 per night
Apartment in Shelburne Falls
Annies’ Place by The Bridge of Flowers ~
$105 per night

Destinations to explore