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Holiday 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
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!
18–25 Feb, Individual Host
£115 per night
Guest favourite
Guest house 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.
2–9 May, Individual Host
£142 per night
Guest favourite
Apartment in Killington
🎿Cozy Fireplace Condo-Mins. to Everything 🚵
Seeking Adventure? This end unit garden level condo is 6 minutes to Killington AND Pico! Quick access to the Appalachian Trail to ATV, mountain bike, hike, and swim. Relaxing? Work remotely with fast Wi-Fi, hang on the porch swing, or unwind in front of the wood fireplace. Hop in the power adjustable king bed, pull the darkening shades, and turn on the sound machine for restful sleep so you can wake up and do it again! A portion of each stay is donated to local VT nonprofits
7–14 Jun
£110 per night

Popular amenities for Windsor County holiday rentals

Other great holiday rentals in Windsor County

Guest favourite
Flat in Lebanon
The Old Farmhouse
12–19 Dec, Individual Host
£103 per night
Guest favourite
Cabin in Rochester
Black haus: a hip, cool house hidden in a forest.
7–14 Jan, Individual Host
£125 per night
Guest favourite
Barn in Woodstock
Stunning Converted Barn Home 3-bed 2 bath
22–29 Apr, Individual Host
£439 per night
Guest favourite
Flat in Woodstock
LOG HOME APARTMENT IN WOODST. VILLAGE 3 night min.
25 Jun – 2 Jul, Professional Host
£170 per night
Guest favourite
Home in Woodstock
Beautiful Woodstock Home-Perfect for entertaining
19–26 May
£530 per night
Guest favourite
Flat in Pittsford
Waterfront cottage walk-out suite.
21–28 May, Individual Host
£92 per night
Guest favourite
Guest house in Hartland
Cottage for Two/Solo Getaway/Musician's Retreat
4–11 Feb, Individual Host
£155 per night
Guest favourite
Guest suite in Royalton
Bluestone Farm
15–22 Apr
£84 per night
Guest favourite
Guest house in Hartland
Yurt In The Woods - Private Refuge
4–11 Sept, Individual Host
£158 per night
Guest favourite
Flat in Claremont
Beautiful 1 bedroom apartment with balcony
27 Nov – 4 Dec
£88 per night
Guest favourite
Apartment in Ludlow
Okemo Ski-in/Ski-out, Steps to lift Condo
8–15 Apr, Individual Host
£145 per night
Superhost
Apartment in Killington
Winter is coming! Cute Mountain Getaway!
7–14 May, Individual Host
£91 per night

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