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Holiday rentals in Windsor County

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Windsor County

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

The Cozy Little Red Cabin
SUPERHOST
Entire cabin · 4 guests · 3 beds · 1 bathroom

The Cozy Little Red CabinThe little red cabin is less than 15 minutes to Okemo Mountain! Authentic Vermont experience situated on a back road with a wood stove. Spacious and cozy all at once! WiFi and a smart TV. One queen and a set of bunk beds accommodate 4 people.

Four Season River Retreat: Private beaches & more!
Entire house · 8 guests · 4 beds · 2 bathrooms

Four Season River Retreat: Private beaches & more!A river paradise! Situated on the iconic Black River, on 4 acres of woods and trails, our newly renovated farmhouse and barn has four bedrooms, two baths, a rec space, three beaches, and can easily host 8 guests. Brewery & hiking just minutes away. Perfect for summer & winter as it is located 12 minutes from Okemo and 40 minutes to Killington. Whether you are looking for a family vacation or a remote workspace, this all-season house is a perfect get-away to enjoy VT any time of the year.

Studio apartment in sunny historic village
Entire guest suite · 3 guests · 2 beds · 1 bathroom

Studio apartment in sunny historic villageThis guest unit is part of a historic 1820's brick cape located in Thetford Center. It's 15 minutes to Hanover NH, and has all the essentials, from cookware to laundry, from air conditioning to a Smart TV. Surrounded by green spaces, from the meadow in the backyard to the village green across the street, it's still close to area attractions.

Holiday rentals for every style

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Popular amenities for Windsor County holiday rentals

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

Other great holiday rentals in Windsor County

  1. Entire cottage
  2. Peru
Moon Beam Cottage--A cozy and welcoming retreat
₹7,414 per night
SUPERHOST
  1. Private room
  2. Weston
Spacious King Suite w/ Breakfast Hills Of Weston
₹10,330 per night
SUPERHOST
  1. Entire flat
  2. Clarendon
Dog heavenly! Private, beautiful and relaxing.
₹6,009 per night
  1. Entire cabin
  2. Royalton
Scandinavian cabin in the woods
₹7,268 per night
SUPERHOST
No reviews yet
  1. Entire cottage
  2. Windsor
Adorable Country Cottage in Hartland w/FIOS
₹11,798 per night
SUPERHOST
  1. Entire cabin
  2. Mount Holly
Private Cabin / Minutes to Okemo
₹9,176 per night
  1. Entire cabin
  2. Ludlow
Beautiful lake cottage close to Okemo Mt
₹10,403 per night
SUPERHOST
  1. Entire townhouse
  2. Fairlee
Garden Retreat, Lake Fairlee, Dartmouth & Skiway
₹8,201 per night
  1. Entire cottage
  2. Pomfret
Space & Time - the retreat you deserve!
₹13,140 per night
SUPERHOST
  1. Tiny house
  2. Clarendon
Secluded tiny house resort - DOG FRIENDLY
₹5,401 per night
SUPERHOST
  1. Entire guest house
  2. Reading
Peaceful Alpine Cottage Retreat with Mountain View
₹11,012 per night
SUPERHOST
  1. Entire cabin
  2. Royalton
Genuine Vermont Sugar House on 70 peaceful acres
₹7,865 per night