Vacation rentals in Windsor County

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Windsor County

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

Guest favorite

Cottage in Hartland

4.97 out of 5 average rating, 417 reviews

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!

Apr 13 – 20

G$25,705 GYD per night
Guest favorite

Guesthouse in Woodstock

4.98 out of 5 average rating, 203 reviews

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.

Nov 2 – 9

G$33,412 GYD per night
Guest favorite

Guest suite in Royalton

4.95 out of 5 average rating, 175 reviews

Private Guest Suite on 155 Acre Royalton Town Farm

1 Bed, 1 Bath apartment attached to historic farm house. This cozy space is the perfect spot for a weekend getaway or a long family vacation on a historic Vermont Farm. Equipped with all the linens and dishes you will need and even a few extras like farm fresh eggs in the fridge and hot chocolate. Close to I-89 and 30 minutes of Ski Resorts like Saskadena Six. Property of 155 acres has trails, sledding hills and our farm animals you can enjoy. Check our reviews, you won't be disappointed!

Apr 11 – 18

G$22,807 GYD per night

Popular amenities for Windsor County vacation rentals

Other great vacation rentals in Windsor County

Guest favorite

Guesthouse in Vershire

4.93 out of 5 average rating, 241 reviews

The Peaceable Kingdom

Oct 29 – Nov 5

G$20,566 GYD per night
Guest favorite

Apartment in Rutland

4.96 out of 5 average rating, 514 reviews

Your home away from home

Nov 26 – Dec 3

G$20,765 GYD per night
Superhost

Condo in Killington

4.81 out of 5 average rating, 225 reviews

Come to Killington this Winter!

Apr 19 – 26

G$17,725 GYD per night
Guest favorite

Tiny home in Hartland

4.94 out of 5 average rating, 251 reviews

Private Modern Cabin w/View of Fields, Hills

Jan 25 – Feb 1

G$27,526 GYD per night
Guest favorite

Apartment in Claremont

4.88 out of 5 average rating, 108 reviews

Beautiful 1 bedroom apartment with balcony

Oct 14 – 21

G$18,659 GYD per night
Guest favorite

Condo in Killington

4.92 out of 5 average rating, 143 reviews

Renovated, w/Covered Parking-Shuttle-Walk to Lifts

May 26 – Jun 2

G$24,817 GYD per night
Superhost

Condo in Ludlow

4.92 out of 5 average rating, 117 reviews

All Season Lovely and Zen Okemo Mt Lodge Condo

May 21 – 28

G$21,032 GYD per night
Guest favorite

Guest suite in Shrewsbury

4.91 out of 5 average rating, 258 reviews

Valley View

May 19 – 26

G$18,931 GYD per night
Guest favorite

Guesthouse in Hartland

4.95 out of 5 average rating, 910 reviews

Yurt In The Woods - Private Refuge

Jan 3 – 10

G$32,770 GYD per night
Guest favorite

Apartment in Hartland

4.87 out of 5 average rating, 437 reviews

Sunny Studio Apartment in Hartland

Aug 28 – Sep 4

G$24,744 GYD per night
Guest favorite

Barn in Woodstock

5.0 out of 5 average rating, 200 reviews

THE LOFT, stunning views from a timber framed barn

Sep 16 – 23

G$67,453 GYD per night
Guest favorite

Guesthouse in Springfield

4.86 out of 5 average rating, 321 reviews

Connecticut River-Cozy Cottage

Dec 1 – 8

G$19,117 GYD per night

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