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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.

The Higgle House: A Sweetwater Farm Stay
Entire guesthouse · 4 guests · 2 beds · 1 bath
The Higgle House: A Sweetwater Farm StayThe Higgle House is the guest house on Sweetwater Farm. It is constructed from salvaged everything. Built from a centuries old barn and turkey coop- the house features original barn boards and lots of old metal roofing. It has a Kitchenette with a small fridge, microwave and countertop cook top and oven and 3/4 Bath. It is located next to our farm's chicken coop so please enjoy fresh eggs, right from under the Chicken's butt!
Downtown Loft above Winery and Distillery
Entire rental unit · 2 guests · 1 bed · 1 bath
Downtown Loft above Winery and DistilleryEnjoy a lovely weekend getaway in this cute 1 bedroom apartment, centrally located in Winchester, NH. Enjoy a free tasting at New England Sweetwater Farm & Distillery next door and a pint on us at Outlaw Brewing Company. This cozy apartment features a full kitchen, 3/4 bath as well as a full 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!
Morning Myst Pines
Entire residential home · 6 guests · 5 beds · 1 bath
Morning Myst PinesHeated, 3 Bedroom, 1 bath, year-round Lakehouse with 35 feet of lakefront footage (Forest Lake ), private dock, offering breathtaking views of the Monadnock region. Plenty of outdoor living space, grill, gazebo with Adirondack chairs overlooking the water, walking distance of town beach/playground.

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Popular amenities for Winchester vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Winchester

  1. Entire guest suite
  2. Winchester
Stay at a craft brewery - Winchester NH
$150 per night
  1. Entire residential home
  2. Winchester
Lakefront Retreat in Winchester, Getaway Ready and Fully Equipped
$299 per night
  1. Entire residential home
  2. Ashuelot
Historic Home on River Covered Bridge Views
$128 per night
  1. Campsite
  2. Winchester
The Fox Den at Whippie Woods
$60 per night
  1. Private room
  2. Northfield
A Healing Forest Space in the Heart of New England
$85 per night
  1. Entire rental unit
  2. Winchester
Beautiful lake side getaway, quiet.
$132 per night
  1. Entire residential home
  2. Winchester
Forest Lake 3BR, 1.5 B Lake front home. Hot Tub
$296 per night
  1. Entire residential home
  2. Northfield
Cozy Home with Relaxing Views
$203 per night
  1. Campsite
  2. Winchester
Whippie Woods Camp Field
$100 per night
  1. Entire cottage
  2. Winchester
Cozy lakefront cottage on Forest Lake
$300 per night
  1. Private room
  2. Swanzey
Cheerful 3 bedroom residential home with fireplace
$48 per night
  1. Private room
  2. Chesterfield
Air bnb 4, Keene, NH Brattlboro VT Honeymoon suite
$193 per night