Skip to content
We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.
Start your search
Location
Windsor
Check in / Check out
Any week
Guests
Add guests
Stays
Experiences
Online Experiences
Where
Search by region
I’m flexible
I’m flexible
Vermont
Vermont
Europe
Europe
Italy
Italy
Caribbean
Caribbean
Mexico
Mexico
Check in
Add dates
Check out
Add dates
Who
Add guests
Search
Airbnb your home
Sign up
Log in
Airbnb your home
Help Center
%{visible} of %{smart_count_str} Airbnb Category showing||||%{visible} of %{smart_count_str} Airbnb Categories showing
Your search
Countryside
Lake
Cabins
Amazing pools
Amazing views
Ski-in/out
Rooms
Farms
Play
Chef's kitchens
Lakefront
Bed & breakfasts
Vineyards
Tiny homes
Off-the-grid
New
Trending
Barns
A-frames
Design
Golfing
Grand pianos
Treehouses
Yurts
Mansions
Camping
Skiing
Filters
0
Display total before taxes
Show map
Search results; Over 1,000 places in Windsor
Over 1,000 places in Windsor
Guest favorite
Guest favorite
Home in Windsor
Modern custom home on a side of Mt Ascutney
5 beds
5 beds
Apr 1 – 6
Apr 1 – 6
G$87,314 GYD
G$79,627 GYD
night
G$79,627 GYD per night, originally G$87,314 GYD
5.0 out of 5 average rating, 49 reviews
5.0 (49)
Condo in West Windsor
Ski-in/out, dog-friendly 3BR with prime location
7 beds
7 beds
Apr 1 – 6
Apr 1 – 6
G$44,377 GYD
night
G$44,377 GYD per night
New place to stay
New
Guest favorite
Guest favorite
Home in West Windsor
Meadow View. 35 acres outside your door!
1 king bed
1 king bed
Apr 14 – 19
Apr 14 – 19
G$42,271 GYD
night
G$42,271 GYD per night
4.98 out of 5 average rating, 160 reviews
4.98 (160)
Guest favorite
Guest favorite
Tiny home in West Windsor
Red Barn Cabin
2 beds
2 beds
Apr 8 – 13
Apr 8 – 13
G$40,985 GYD
night
G$40,985 GYD per night
5.0 out of 5 average rating, 12 reviews
5.0 (12)
Guest favorite
Guest favorite
Cabin in West Windsor
Sunset Cabin - your private romantic hideaway
1 queen bed
1 queen bed
May 7 – 12
May 7 – 12
G$35,395 GYD
night
G$35,395 GYD per night
4.98 out of 5 average rating, 205 reviews
4.98 (205)
Guest favorite
Guest favorite
Cottage in Hartland
Hartland - Adorable Cottage w/FIOS - Pet Friendly
2 beds
2 beds
Apr 10 – 15
Apr 10 – 15
G$40,985 GYD
night
G$40,985 GYD per night
4.92 out of 5 average rating, 83 reviews
4.92 (83)
Guest favorite
Guest favorite
Guesthouse in Hartland
Yurt In The Woods - Private Refuge
3 queen beds
3 queen beds
Apr 1 – 6
Apr 1 – 6
G$33,462 GYD
night
G$33,462 GYD per night
4.95 out of 5 average rating, 910 reviews
4.95 (910)
Guest favorite
Guest favorite
Apartment in Hartland
Hearth House Farm
4 beds
4 beds
Apr 1 – 6
Apr 1 – 6
G$30,468 GYD
night
G$30,468 GYD per night
4.96 out of 5 average rating, 99 reviews
4.96 (99)
Guest favorite
Guest favorite
Cabin in West Windsor
Cowshed Cabin Farm & Stable
4 beds
4 beds
Nov 1 – 6
Nov 1 – 6
G$30,113 GYD
night
G$30,113 GYD per night
4.97 out of 5 average rating, 125 reviews
4.97 (125)
Guest favorite
Guest favorite
Home in West Windsor
Escape To Outdoor Adventures at Mount Ascutney
4 beds
4 beds
Apr 1 – 6
Apr 1 – 6
G$55,500 GYD
G$48,882 GYD
night
G$48,882 GYD per night, originally G$55,500 GYD
5.0 out of 5 average rating, 45 reviews
5.0 (45)
Guest favorite
Guest favorite
Home in Plainfield
The Oaks - secluded rural estate w/ amazing views
3 beds
3 beds
Apr 9 – 14
Apr 9 – 14
G$43,319 GYD
night
G$43,319 GYD per night
4.87 out of 5 average rating, 76 reviews
4.87 (76)
Home in Cornish
Cornish-Windsor Bridge Retreat with Amazing Views
9 beds
9 beds
Apr 7 – 12
Apr 7 – 12
G$71,096 GYD
night
G$71,096 GYD per night
5.0 out of 5 average rating, 4 reviews
5.0 (4)
Guest favorite
Guest favorite
Home in West Windsor
3BR Vermont Charm: Fireplace, Ski Access, Barn
6 beds
6 beds
Apr 1 – 6
Apr 1 – 6
G$56,104 GYD
night
G$56,104 GYD per night
5.0 out of 5 average rating, 55 reviews
5.0 (55)
Superhost
Superhost
Condo in Hartford
Christian Street Condos #2
6 queen beds
6 queen beds
Apr 1 – 6
Apr 1 – 6
G$36,187 GYD
night
G$36,187 GYD per night
New place to stay
New
Guest favorite
Guest favorite
Cabin in West Windsor
Cozy Log Cabin w/ Incredible Mountain View
4 beds
4 beds
Apr 2 – 7
Apr 2 – 7
G$101,865 GYD
night
G$101,865 GYD per night
5.0 out of 5 average rating, 14 reviews
5.0 (14)
Guest favorite
Guest favorite
Home in West Windsor
Firewheel Hill: Private, contemporary house
6 beds
6 beds
Apr 10 – 15
Apr 10 – 15
G$60,641 GYD
night
G$60,641 GYD per night
4.98 out of 5 average rating, 127 reviews
4.98 (127)
Superhost
Superhost
Home in West Windsor
Ascutney Mountain House
5 beds
5 beds
Apr 21 – 26
Apr 21 – 26
G$67,208 GYD
night
G$67,208 GYD per night
4.86 out of 5 average rating, 29 reviews
4.86 (29)
Guest favorite
Guest favorite
Home in Cavendish
VT Cabin close to Okemo and Killington
Apr 1 – 6
Apr 1 – 6
G$76,454 GYD
G$59,437 GYD
night
G$59,437 GYD per night, originally G$76,454 GYD
5.0 out of 5 average rating, 6 reviews
5.0 (6)
1
2
3
4
…
15