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Vacation rentals in Winchester

Vacation rentals in Winchester

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Winchester

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

Stay at a craft brewery - Winchester NH
SUPERHOST
Entire guest suite · 3 guests · 1 bed · 1 bath

Stay at a craft brewery - Winchester NHRent our one bedroom private suite at The Outlaw Brewing Company. Walk across the lawn to the taproom to sample our small batch craft beer. Several brews that 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 on over for a fun get away at a unique location. Two night minimum stay, no security deposit, no extra people charge, no additional cleaning fee.

CAT's Croft - A little farm with a big view!
Private room · 6 guests · 3 beds · 1 shared bath

CAT's Croft - A little farm with a big view!A cozy country home, we're surrounded by hay fields with big sky and beautiful views with many amenities nearby. Conveniently located 1 mile off Route 91, with easy access to points north (Brattleboro, VT, 15 minutes) and points south (Northampton, MA, 40 minutes). We welcome all walks of life and we are 420 friendly. Please read the listing details for more information.

Forest Lake 4BR,2B! Lakefront,Hot Tub, Boats, Fun!
Entire house · 10 guests · 6 beds · 1.5 baths

Forest Lake 4BR,2B! Lakefront,Hot Tub, Boats, Fun!Private Direct Lakefront Home on Forest Lake, Winchester, NH with a Hot Tub! We currently have a long term guest until May '21. Book for summer or Fall now! Four bedrooms,1.5 bath, Gourmet Kitchen, Great Room ,skylights & fireplace overlooking the Lake, 3 decks. 3 kayaks, Canoe, Ping Pong, WIFI, Air Hockey, bikes, kids cars, crib, books, games, sports equipment for both summer and winter. Wood for firepit & stove. Fantastic Sunsets overlooking the Lake. Rails to Trails Mt Monadnock close

Vacation rentals for every style

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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

~Serene Barn Retreat~
SUPERHOSTEntire apartment
~Serene Barn Retreat~
Price:$81 / night
Majestic Mountain View’s
Entire house
Majestic Mountain View’s
Price:$190 / night
Varykino Cottage @ 252 Sunset Road, Fitzwilliam NH
Entire house
Varykino Cottage @ 252 Sunset Road, Fitzwilliam NH
Price:$104 / night
Hickory Hill Treetop Apartment
SUPERHOSTEntire guest suite
Hickory Hill Treetop Apartment
Price:$85 / night
Cozy little carriage apartment close to downtown
Entire apartment
Cozy little carriage apartment close to downtown
Price:$95 / night
Quiet, Cozy & Great location for exploring VT !
SUPERHOSTEntire apartment
Quiet, Cozy & Great location for exploring VT !
Price:$69 / night
Traveling Nurses - Clean, Safe, One Bedroom Apart.
Entire apartment
Traveling Nurses - Clean, Safe, One Bedroom Apart.
Price:$47 / night
Tanglebloom Cabin | Glamping Nature Experience
SUPERHOSTFarm stay
Tanglebloom Cabin | Glamping Nature Experience
Price:$91 / night
Discover Vermont ! Clean & Quiet Studio Apt.
SUPERHOSTEntire condominium
Discover Vermont ! Clean & Quiet Studio Apt.
Price:$69 / night
Beautifully renovated three bedroom
SUPERHOSTEntire apartment
Beautifully renovated three bedroom
Price:$99 / night
Rustic-Chic Cottage w/ Yard & Grill - Near Hiking!
Entire cottage
Rustic-Chic Cottage w/ Yard & Grill - Near Hiking!
Price:$112 / night
Private Studio apt. private bath, coded door locks
SUPERHOSTEntire apartment
Private Studio apt. private bath, coded door locks
Price:$70 / night
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