Vacation rentals in Windsor County

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Top-rated holiday rentals in Windsor County

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

Guest favourite
Apartment in Lebanon
The Old Farmhouse
This is a farm house style lodging with the apartment as seen,on the second floor accessible with stairs. Bathroom with stand up shower. Fully furnished Kitchen. 2 Bedrooms with queen beds. There is Wifi ,TV, and a work table. Located in the heart of the Upper Valley. In town on the Main Street. We are 5 miles to Dartmouth College and Hospital. Close to retail,restaurants. We have been vaccinated , boosted, would like to remain contact-free when possible. We are available if you have questions.
27 June – 4 July
4.83 out of 5 average rating, 280 reviews
Guest favourite
Cottage in Hartland
Breeze Hill Cottage
This cozy two bedroom home sits on a rural dirt road overlooking fields, woods, and the NH mountains. Watch birds from the window, relax on the patio, and enjoy the flower gardens. The cottage boasts modern amenities mixed with antiques. Please note: if we don’t respond to an Airbnb message and you need to speak with us, call us on our phones day or night!!! We have had people message us when we were asleep and so we have not been aware and have not responded. Call us! We will hear the phone!
21 – 28 Sept
4.97 out of 5 average rating, 415 reviews
Guest favourite
Guesthouse in Woodstock
Cozy Little Spot (Self Check-in)
Contactless check-in. Cozy guest house, cabin-studio-getaway; enjoy the sounds of a stream outside the window (next to the bed). Views of a larger brook below. The"Cabin"is nestled in the trees giving a feeling of floating above the brook below. The interior is decorated w/family heirlooms gathered from around the country. Nothing fancy, just a cozy simple getaway. 3.25 mi from town. Choose from a variety of activities in town or hop on nearby trails. NO PETS ALLOWED. ZERO CONTACT WITH OWNERS.
13 – 20 Nov
4.98 out of 5 average rating, 203 reviews

Popular amenities for Windsor County holiday rentals

Other great holiday rentals in Windsor County

Guest favourite
Apartment in Rutland
Your home away from home
19 – 26 July
4.95 out of 5 average rating, 509 reviews
Guest favourite
Apartment in Royalton
Quiet Vermont Get Away
14 – 21 Apr
4.98 out of 5 average rating, 146 reviews
Guest favourite
Guesthouse in Hartland
Yurt In The Woods - Private Refuge
19 – 26 Sept
4.95 out of 5 average rating, 904 reviews
Guest favourite
Guesthouse in Hartland
Cottage for Two/Solo Getaway/Musician's Retreat
10 – 17 Sept
4.96 out of 5 average rating, 158 reviews
Guest favourite
Condo in Killington
🎿Cozy Fireplace Condo-Mins. to Everything 🚵
7 – 14 June
4.95 out of 5 average rating, 119 reviews
Guest favourite
Apartment in Woodstock
LOG HOME APARTMENT IN WOODST. VILLAGE 3 night min.
20 – 27 Aug
4.96 out of 5 average rating, 170 reviews
Guest favourite
Home in Woodstock
Beautiful Woodstock Home-Perfect for entertaining
13 – 20 Sept
5.0 out of 5 average rating, 109 reviews
Guest favourite
Apartment in Pittsford
Waterfront cottage walk-out suite.
28 May – 4 June
4.99 out of 5 average rating, 115 reviews
Guest favourite
Cabin in West Windsor
Sunset Cabin - your private romantic hideaway
24 – 31 July
4.98 out of 5 average rating, 205 reviews
Guest favourite
Cottage in Reading
Shattuck Hill Cottage
27 Dec – 3 Jan
4.95 out of 5 average rating, 128 reviews
Guest favourite
Barn in Woodstock
Stunning Converted Barn Home 3-bed 2 bath
27 Feb – 6 Mar
5.0 out of 5 average rating, 116 reviews
Guest favourite
Cabin in Rochester
Black haus: a hip, cool house hidden in a forest.
13 – 20 Feb
4.95 out of 5 average rating, 383 reviews

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