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Vacation Rentals in Windsor, VT
Vacation Rentals
USA
Vermont (VT)
Vacation Rentals in Windsor, VT
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Windsor
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Bedrooms
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Amenities
Internet or Wifi (45)
Air Conditioning (33)
Washer/Dryer (30)
Fireplace (24)
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Suitability
Kid friendly (42)
Pet friendly (20)
Smoking allowed (2)
Wheelchair access (0)
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Property type
Vacation Rental House (41)
Condominium/Apartment (5)
Cabin Vacation Rental (0)
Private Room (0)
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Distinctive Features
Private Chef (0)
Private Beach (0)
Waterfront (0)
Ski In/Ski Out (0)
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Distance from
5 km
Cornish-Windsor Covered Bridge
Harpoon Brewery
American Precision Museum
Artisans Park
Cider Hill Gardens
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46 rentals
in Windsor.
Vermont cabin on 20 acres in open field
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 5
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As seen on
Experience life on a Vermont Farm in a Beautiful Modern Cabin - Stunning Views!
1
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
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Stunning Modern Cabin on Beautiful Vermont Farm
1
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
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As seen on
Experience life on a Vermont Farm in a Beautiful Modern Cabin - Stunning Views!
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
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As seen on
Experience life on a Vermont Farm in a Beautiful Modern Cabin - Stunning Views!
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps
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As seen on
Beautiful Modern Cabin on a Vermont Farm - Stunning Panoramic Views!
2
Holiday Rental House
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3 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps
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As seen on
Lovely Vermont Cabin on a quiet street
4
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 7
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Private wing of the Largest Colonial Revival Mansion in the US
Holiday Rental House
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3 bedrooms
4 bathrooms
Sleeps 7
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Totally Restored Grand Mansion & Estate overlooking the CT River
Holiday Rental House
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16 bedrooms
19 bathrooms
Sleeps 39
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The following properties within 32 kms of Windsor match all your filters:
Dog-friendly, 2-story condo at the base of Ascutney with fireplace & balcony
8
Condo/Apartment
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3 bedrooms
3 bathrooms
Sleeps 8
Match:
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Remote Getaway near Woodstock Vermont
10
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 6
Match:
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Country Home next to Blow-Me-Down Covered Bridge in the Old Cornish Art Colony!
10
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
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As seen on
Beautiful Fall & Winter Views - Rustic Contemporary Cabin on Mt Ascutney
17
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 6
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Log manor on 65 private acres of land with entertaining amenities & hot tub
5
Holiday Rental House
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4 bedrooms
4 bathrooms
Sleeps 8
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Spruce Moose Cottage | Tiny House on 65 private acres
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
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As seen on
Rockledge Farm country living
14
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
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Sunset Cabin - your private romantic hideaway
1
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
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As seen on
Vermont Villa Near the Trails
2
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
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Meadow View- 35 Acres outside your door
29
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 4
Match:
Sleeps
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Enjoy snowball fights or romantic nights in a 1BD vacation apartment
2
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 4
Match:
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Cozy Historic Hilltop Cottage with Mount Ascutney View
70
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
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As seen on
Villa with a Fireplace Near the Trails
10
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 6
Match:
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As seen on
Ronnoco Farm-Charming Brownsville/West Windsor, VT cottage
8
Holiday Rental House
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3 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps
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As seen on
Lovely 2 Bedroom Townhouse on Ascutney Mountain
5
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 4
Match:
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As seen on
Romantic Getaway or Family winter adventures in 2BD w/resort activities
Condo/Apartment
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
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Villa with Pool + Fitness Center Access
10
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 10
Match:
Sleeps
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As seen on
Villa Near Biking and Hiking Trails
2
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
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As seen on
Come spend Christmas break in Vermont, Close to skiing!
10
Holiday Rental House
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3 bedrooms
1 bathroom
Sleeps 8
Match:
Sleeps
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As seen on
Long Range Mountain Views in West Windsor
10
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 4
Match:
Sleeps
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As seen on
Beautiful home offering privacy on 7 acres with private pond
12
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
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As seen on
Country living at its best
3
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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Beautiful craftsman-built home with natural wood and large windows in every room
12
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
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As seen on
Inviting Vermont Home On Mount Ascutney!
10
Holiday Rental House
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6 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
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As seen on
Meriden Village of Plainfield Home w/ Backyard
3
Holiday Rental House
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6 bedrooms
2 bathrooms
Sleeps 9
Match:
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As seen on
Pet-Friendly Claremont Vacation Rental!
2
Holiday Rental House
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5 bedrooms
2 bathrooms
Sleeps 9
Match:
Sleeps
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As seen on
Log Cabin home with Mt Ascutney views and pool table
48
Holiday Rental House
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5 bedrooms
4 bathrooms
Sleeps 14
Match:
Sleeps
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Luxury Vermont Vacation Rental: Private Hot Tub!
2
Holiday Rental House
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7 bedrooms
4 bathrooms
Sleeps 12
Match:
Sleeps
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Secluded Luxury Home on Huge Property with Mountain Views - Near Slopes
57
Holiday Rental House
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5 bedrooms
4 bathrooms
Sleeps 10
Match:
Sleeps
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As seen on
5 Star Accommodation Meets Farm Life #hartlandhillfarm
10
Holiday Rental House
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5 bedrooms
7 bathrooms
Sleeps 12
Match:
Sleeps
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Secluded home w/covered porch and alpine views, near ski resorts, w/foosball
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
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Rock Haven Sugar House | Field and Farm
1
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
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Ski-in/out, dog-friendly condo with prime location for skiing & hiking
3
Condo/Apartment
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4 bedrooms
3 bathrooms
Sleeps 9
Match:
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Enchanting farmhouse with a picture perfect view of Mt. Ascutney
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 8
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This cabin is a 3 bedroom(s), 3.5 bathrooms, located in West Windsor, VT.
Holiday Rental House
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3 bedrooms
4 bathrooms
Sleeps 6
Match:
Sleeps
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Luxury Home, Dog Suite | Rock Haven Carriage House
Condo/Apartment
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1 bedroom
2 bathrooms
Sleeps 4
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Sleeps
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Private mountain setting w/ open rooms, hiking, biking, skiing at your
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 6
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1
Showing results 1-46 of 46
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:
Vermont cabin on 20 acres in open field
Experience life on a Vermont Farm in a Beautiful Modern Cabin - Stunning Views!
Stunning Modern Cabin on Beautiful Vermont Farm
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:
Vermont cabin on 20 acres in open field
Experience life on a Vermont Farm in a Beautiful Modern Cabin - Stunning Views!
Stunning Modern Cabin on Beautiful Vermont Farm
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:
Experience life on a Vermont Farm in a Beautiful Modern Cabin - Stunning Views!
Stunning Modern Cabin on Beautiful Vermont Farm
Experience life on a Vermont Farm in a Beautiful Modern Cabin - Stunning Views!
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:
Experience life on a Vermont Farm in a Beautiful Modern Cabin - Stunning Views!
Stunning Modern Cabin on Beautiful Vermont Farm
Experience life on a Vermont Farm in a Beautiful Modern Cabin - Stunning Views!
See all kid friendly vacation rentals in Windsor on Tripadvisor
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