We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows:
Internet Explorer
,
Mozilla Firefox
,
Google Chrome
. Mac:
Safari
.
Flights
Vacation Rentals
Restaurants
Things to do
Skip to main content
Review
Trips
Alerts
Sign in
Inbox
See all
Sign in
to get trip updates and message other travelers.
Windsor
Windsor Tourism
Windsor Hotels
Windsor Bed and Breakfast
Windsor Vacation Rentals
Windsor Vacation Packages
Flights to Windsor
Things to Do in Windsor
Windsor Travel Forum
Windsor Photos
Windsor Map
Windsor Travel Guide
Hotels
All Windsor Hotels
Windsor Hotel Deals
By Hotel Class
Near Airports
Near Colleges
5-stars Hotels in Windsor
4-stars Hotels in Windsor
3-stars Hotels in Windsor
Hotels near (MHT) Manchester Municipal Airport
Hotels near (LEB) Lebanon Regional Airport
Hotels near (RUT) Rutland Airport
Hotels near River Valley Community College
Things to do
Restaurants
Flights
Vacation Rentals
Shopping
Vacation Packages
Cruises
Rental Cars
Tours
Add a Place
Travel Forum
Airlines
Best of 2022
Road Trips
Help Center
Travel Articles
Vacation Rentals in Windsor, VT
Vacation Rentals
USA
Vermont (VT)
Vacation Rentals in Windsor, VT
Search
Windsor Vacation Rentals
List your property
Owner log in
Check in
— / — / —
Check out
— / — / —
Guests
0 rooms, 2+ guests
View Map
Bedrooms
Any
Bathrooms
Any
Amenities
Parking (47)
Internet (38)
Air Conditioning (30)
Washer/Dryer (30)
Show more
Suitability
Kid friendly (43)
Wheelchair access (4)
Pet friendly (4)
Smoking allowed (4)
Show more
Property type
Vacation Rental House (48)
Condominium/Apartment (2)
Cabin Vacation Rental (0)
Private Room (0)
Show more
Distinctive Features
Boat Available (4)
Mountain Views (2)
Water Views (1)
Staffed Property (1)
Show more
Distance from
1 mi
50 rentals
in Windsor.
Sort by:
Tripadvisor Sort
Experience life on a Vermont Farm in a Beautiful Modern Cabin - Stunning Views!
1 review
Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match:
Sleeps
More info
Check in
Check out
Show Prices
Stunning Modern Cabin on Beautiful Vermont Farm
1 review
Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match:
Sleeps
More info
Check in
Check out
Show Prices
Vermont cabin on 20 acres in open field
Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match:
Sleeps
More info
Check in
Check out
Show Prices
Experience life on a Vermont Farm in a Beautiful Modern Cabin - Stunning Views!
Rental Home
1 bedroom
1 bathroom
Sleeps 6
Match:
Sleeps
More info
Check in
Check out
Show Prices
Scenic South Woodstock, Vermont home
46 reviews
Rental Home
4 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check in
Check out
Show Prices
Woodstock Farmhouse Completely Updated Close to Town & Ski Areas
49 reviews
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check in
Check out
Show Prices
Panoramic Mountain View, Lots To Do, Or Enjoy Doing Nothing
39 reviews
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check in
Check out
Show Prices
Vacation/Travelers Apartment At Clay Hill Corners Blueberry Farm
30 reviews
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match:
Sleeps
More info
Check in
Check out
Show Prices
Beautiful craftsman-built home with natural wood and large windows in every room
27 reviews
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check in
Check out
Show Prices
Idyllic: c.1842 farmhouse on 26 acres with breathtaking view of the mountains
32 reviews
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check in
Check out
Show Prices
Save time - get the best
Windsor
rentals sent straight to your email!
Get the List
Cozy Historic Hilltop Cottage with Mount Ascutney View
59 reviews
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
More info
Check in
Check out
Show Prices
Meadow View- 35 Acres outside your door
28 reviews
Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match:
Sleeps
More info
Check in
Check out
Show Prices
Secluded Get Away Retreat
38 reviews
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check in
Check out
Show Prices
Country Home next to Blow-Me-Down Covered Bridge in the Old Cornish Art Colony!
25 reviews
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check in
Check out
Show Prices
Dog Friendly Home in S. Woodstock
19 reviews
Rental Home
3 bedrooms
3 bathrooms
Sleeps 7
Match:
Sleeps
More info
Check in
Check out
Show Prices
Village Farmhouse - Okemo, Ascutney, Green Mountain Horse Assoc. Pet-friendly.
33 reviews
Rental Home
4 bedrooms
1 bathroom
Sleeps 8
Match:
Sleeps
More info
Check in
Check out
Show Prices
Beautiful Guest House Set Among the Trees
19 reviews
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
More info
Check in
Check out
Show Prices
The Real Vermont All Seasons Get-Away Home - Part of Queche Lakes Country Club
28 reviews
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check in
Check out
Show Prices
Secluded, deluxe home with mountain view - close to hiking, skiing, & fishing
51 reviews
Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match:
Sleeps
More info
Check in
Check out
Show Prices
New to VRBO Fully Renovated and Furnished Home on Quechee Lakes Golf Courses
18 reviews
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check in
Check out
Show Prices
Sunset Cabin - your private romantic hideaway
17 reviews
Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
More info
Check in
Check out
Show Prices
Exquisite Log Home with views near Woodstock, Vt.
10 reviews
Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match:
Sleeps
More info
Check in
Check out
Show Prices
Spectacular Views At This Luxury Country Estate, Walking Distance To Town
10 reviews
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check in
Check out
Show Prices
NEW! Available Sept. 11. Long Range Mountain Views in West Windsor
10 reviews
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check in
Check out
Show Prices
5 Star Accommodation Meets Farm Life #hartlandhillfarm
9 reviews
Rental Home
5 bedrooms
7 bathrooms
Sleeps 12
Match:
Sleeps
More info
Check in
Check out
Show Prices
NEW LISTING! Hartland Bungalow
9 reviews
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
More info
Check in
Check out
Show Prices
Splendid 1920s Vermont Farmhouse
7 reviews
Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match:
Sleeps
More info
Check in
Check out
Show Prices
Remote Getaway in Southern Vermont
9 reviews
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps
More info
Check in
Check out
Show Prices
Classic Vermont home w/hot tub, deck & wood stove-near Okemo Mountain Resort
12 reviews
Rental Home
3 bedrooms
2 bathrooms
Sleeps 13
Match:
Sleeps
More info
Check in
Check out
Show Prices
Riverside Retreat w/Deck by Cornish-Windsor Bridge
11 reviews
Rental Home
6 bedrooms
3 bathrooms
Sleeps 10
Match:
Sleeps
More info
Check in
Check out
Show Prices
Blue Forest Farm Estate - Extraordinary 326 Acres with Two Separate Rentals!
4 reviews
Rental Home
6 bedrooms
6 bathrooms
Sleeps 15
Match:
Sleeps
More info
Check in
Check out
Show Prices
Luxury 4 Bedroom / 3.5 Bath Private Home with Enclosed Porch & Game Room
5 reviews
Rental Home
4 bedrooms
4 bathrooms
Sleeps 12
Match:
Sleeps
More info
Check in
Check out
Show Prices
Village Farmhouse - mins to GMHA, Okemo, Killington. Pet-friendly.
3 reviews
Rental Home
4 bedrooms
1 bathroom
Sleeps 8
Match:
Sleeps
More info
Check in
Check out
Show Prices
Payment Protection
NEW! - 2 Bedroom / 1 Bath Riverside Cottage
7 reviews
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
More info
Check in
Check out
Show Prices
Reading Farms Estate/ Vermont Luxury Rental
5 reviews
Rental Home
15 bedrooms
12 bathrooms
Sleeps 46
Match:
Sleeps
More info
Check in
Check out
Show Prices
Payment Protection
Havenwood, a beautiful private, gated estate in Woodstock, Vermont
2 reviews
Rental Home
7 bedrooms
8 bathrooms
Sleeps 14
Match:
Sleeps
More info
Check in
Check out
Show Prices
Beautiful Modern Cabin on a Vermont Farm - Stunning Panoramic Views!
1 review
Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps
More info
Check in
Check out
Show Prices
Cozy Historic Hilltop Cottage
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
More info
Check in
Check out
Show Prices
Payment Protection
Tentrr Signature Site - The Perch
Rental Home
1 bedroom
1 bathroom
Sleeps 6
Match:
Sleeps
More info
Check in
Check out
Show Prices
Payment Protection
Tentrr Signature Site - The Perch
Rental Home
1 bedroom
1 bathroom
Sleeps 6
Match:
Sleeps
More info
Check in
Check out
Show Prices
* NEW! The Cottage at Reading Farms Estate
Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match:
Sleeps
More info
Check in
Check out
Show Prices
Tentrr Signature Site - Ascutney View
Rental Home
1 bedroom
1 bathroom
Sleeps 6
Match:
Sleeps
More info
Check in
Check out
Show Prices
Payment Protection
Tentrr Signature Site - Ascutney View
Rental Home
0 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps
More info
Check in
Check out
Show Prices
* NEW in 2019! All inclusive 400 acre resort estate
Rental Home
8 bedrooms
10 bathrooms
Sleeps 20
Match:
Sleeps
More info
Check in
Check out
Show Prices
* NEW!! The BARN at Reading Farms Estate
Rental Home
3 bedrooms
2 bathrooms
Sleeps 12
Match:
Sleeps
More info
Check in
Check out
Show Prices
Experience life on a Vermont Farm in a Beautiful Modern Cabin - Stunning Views!
Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match:
Sleeps
More info
Check in
Check out
Show Prices
Guest House at Blue Forest Farm Estate - Spectacular 326 Acre Estate!
Rental Home
4 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check in
Check out
Show Prices
Serene Vermont Retreat
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check in
Check out
Show Prices
Chase House Inn - Edwin Stanton Room
Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
More info
Check in
Check out
Show Prices
Payment Protection
1820 House
Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match:
Sleeps
More info
Check in
Check out
Show Prices
Payment Protection
Previous
Next
1
Frequently Asked Questions about Windsor
Do any vacation rentals in Windsor have a pool?
Yes, here are some popular vacation rentals in Windsor that have a pool:\n
\n
Vermont cabin on 20 acres in open field
\n
Experience life on a Vermont Farm in a Beautiful Modern Cabin - Stunning Views!
\n
Experience life on a Vermont Farm in a Beautiful Modern Cabin - Stunning Views!
\n
\n
See all vacation rentals with a pool in Windsor on Tripadvisor
Do any vacation rentals in Windsor have internet access?
Yes, here are some popular vacation rentals in Windsor that have internet access:\n
\n
Vermont cabin on 20 acres in open field
\n
Experience life on a Vermont Farm in a Beautiful Modern Cabin - Stunning Views!
\n
Experience life on a Vermont Farm in a Beautiful Modern Cabin - Stunning Views!
\n
\n
See all vacation rentals in Windsor on Tripadvisor
What are the best pet friendly rentals in Windsor?
The best pet friendly rentals in Windsor are:\n
\n
Vermont cabin on 20 acres in open field
\n
Experience life on a Vermont Farm in a Beautiful Modern Cabin - Stunning Views!
\n
Experience life on a Vermont Farm in a Beautiful Modern Cabin - Stunning Views!
\n
\n
See all pet friendly vacation rentals in Windsor on Tripadvisor
What are some great rentals in Windsor that are kid friendly?
Some of the most popular kid friendly rentals in Windsor are:\n
\n
Experience life on a Vermont Farm in a Beautiful Modern Cabin - Stunning Views!
\n
Experience life on a Vermont Farm in a Beautiful Modern Cabin - Stunning Views!
\n
Stunning Modern Cabin on Beautiful Vermont Farm
\n
\n
See all kid friendly vacation rentals in Windsor on Tripadvisor