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Search results; Over 1,000 places in Windsor

Guest favorite
Home in Windsor
Modern custom home on a side of Mt Ascutney
5 beds
Apr 1 – 6
5.0 out of 5 average rating, 49 reviews
Condo in West Windsor
Ski-in/out, dog-friendly 3BR with prime location
7 beds
Apr 1 – 6
New place to stay
Guest favorite
Home in West Windsor
Meadow View. 35 acres outside your door!
1 king bed
Apr 14 – 19
4.98 out of 5 average rating, 160 reviews
Guest favorite
Tiny home in West Windsor
Red Barn Cabin
2 beds
Apr 8 – 13
5.0 out of 5 average rating, 12 reviews
Guest favorite
Cabin in West Windsor
Sunset Cabin - your private romantic hideaway
1 queen bed
May 7 – 12
4.98 out of 5 average rating, 205 reviews
Guest favorite
Cottage in Hartland
Hartland - Adorable Cottage w/FIOS - Pet Friendly
2 beds
Apr 10 – 15
4.92 out of 5 average rating, 83 reviews
Guest favorite
Guesthouse in Hartland
Yurt In The Woods - Private Refuge
3 queen beds
Apr 1 – 6
4.95 out of 5 average rating, 910 reviews
Guest favorite
Apartment in Hartland
Hearth House Farm
4 beds
Apr 1 – 6
4.96 out of 5 average rating, 99 reviews
Guest favorite
Cabin in West Windsor
Cowshed Cabin Farm & Stable
4 beds
Nov 1 – 6
4.97 out of 5 average rating, 125 reviews
Guest favorite
Home in West Windsor
Escape To Outdoor Adventures at Mount Ascutney
4 beds
Apr 1 – 6
5.0 out of 5 average rating, 45 reviews
Guest favorite
Home in Plainfield
The Oaks - secluded rural estate w/ amazing views
3 beds
Apr 9 – 14
4.87 out of 5 average rating, 76 reviews
Home in Cornish
Cornish-Windsor Bridge Retreat with Amazing Views
9 beds
Apr 7 – 12
5.0 out of 5 average rating, 4 reviews
Guest favorite
Home in West Windsor
3BR Vermont Charm: Fireplace, Ski Access, Barn
6 beds
Apr 1 – 6
5.0 out of 5 average rating, 55 reviews
Superhost
Condo in Hartford
Christian Street Condos #2
6 queen beds
Apr 1 – 6
New place to stay
Guest favorite
Cabin in West Windsor
Cozy Log Cabin w/ Incredible Mountain View
4 beds
Apr 2 – 7
5.0 out of 5 average rating, 14 reviews
Guest favorite
Home in West Windsor
Firewheel Hill: Private, contemporary house
6 beds
Apr 10 – 15
4.98 out of 5 average rating, 127 reviews
Superhost
Home in West Windsor
Ascutney Mountain House
5 beds
Apr 21 – 26
4.86 out of 5 average rating, 29 reviews
Guest favorite
Home in Cavendish
VT Cabin close to Okemo and Killington
Apr 1 – 6
5.0 out of 5 average rating, 6 reviews