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Windsor Vacation Rentals

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Bedrooms

Bathrooms

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5 km
46 rentals in Windsor.
Vermont cabin on 20 acres in open field, vacation rental in Windsor
Vermont cabin on 20 acres in open field, vacation rental in Windsor
Vermont cabin on 20 acres in open field, vacation rental in Windsor

Vermont cabin on 20 acres in open field

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Experience life on a Vermont Farm in a Beautiful Modern Cabin - Stunning Views!, vacation rental in Windsor
Experience life on a Vermont Farm in a Beautiful Modern Cabin - Stunning Views!, vacation rental in Windsor
Experience life on a Vermont Farm in a Beautiful Modern Cabin - Stunning Views!, vacation rental in Windsor

Experience life on a Vermont Farm in a Beautiful Modern Cabin - Stunning Views!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Stunning Modern Cabin on Beautiful Vermont Farm, vacation rental in Windsor
Stunning Modern Cabin on Beautiful Vermont Farm, vacation rental in Windsor
Stunning Modern Cabin on Beautiful Vermont Farm, vacation rental in Windsor

Stunning Modern Cabin on Beautiful Vermont Farm

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Experience life on a Vermont Farm in a Beautiful Modern Cabin - Stunning Views!, vacation rental in Windsor
Experience life on a Vermont Farm in a Beautiful Modern Cabin - Stunning Views!, vacation rental in Windsor
Experience life on a Vermont Farm in a Beautiful Modern Cabin - Stunning Views!, vacation rental in Windsor

Experience life on a Vermont Farm in a Beautiful Modern Cabin - Stunning Views!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Experience life on a Vermont Farm in a Beautiful Modern Cabin - Stunning Views!, vacation rental in Windsor
Experience life on a Vermont Farm in a Beautiful Modern Cabin - Stunning Views!, vacation rental in Windsor
Experience life on a Vermont Farm in a Beautiful Modern Cabin - Stunning Views!, vacation rental in Windsor

Experience life on a Vermont Farm in a Beautiful Modern Cabin - Stunning Views!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Beautiful Modern Cabin on a Vermont Farm - Stunning Panoramic Views!, vacation rental in Windsor
Beautiful Modern Cabin on a Vermont Farm - Stunning Panoramic Views!, vacation rental in Windsor
Beautiful Modern Cabin on a Vermont Farm - Stunning Panoramic Views!, vacation rental in Windsor

Beautiful Modern Cabin on a Vermont Farm - Stunning Panoramic Views!

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Lovely Vermont Cabin on a quiet street, vacation rental in Windsor
Lovely Vermont Cabin on a quiet street, vacation rental in Windsor
Lovely Vermont Cabin on a quiet street, vacation rental in Windsor

Lovely Vermont Cabin on a quiet street

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Private wing of the Largest Colonial Revival Mansion in the US, vacation rental in Windsor
Private wing of the Largest Colonial Revival Mansion in the US, vacation rental in Windsor
Private wing of the Largest Colonial Revival Mansion in the US, vacation rental in Windsor

Private wing of the Largest Colonial Revival Mansion in the US

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
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Totally Restored Grand Mansion & Estate overlooking  the CT River, vacation rental in Windsor
Totally Restored Grand Mansion & Estate overlooking  the CT River, vacation rental in Windsor
Totally Restored Grand Mansion & Estate overlooking  the CT River, vacation rental in Windsor

Totally Restored Grand Mansion & Estate overlooking the CT River

Holiday Rental House
16 bedrooms
19 bathrooms
Sleeps 39
Match: Sleeps
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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, vacation rental in Windsor
Dog-friendly, 2-story condo at the base of Ascutney with fireplace & balcony, vacation rental in Windsor
Dog-friendly, 2-story condo at the base of Ascutney with fireplace & balcony, vacation rental in Windsor

Dog-friendly, 2-story condo at the base of Ascutney with fireplace & balcony

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Remote Getaway near Woodstock Vermont, vacation rental in Windsor
Remote Getaway near Woodstock Vermont, vacation rental in Windsor
Remote Getaway near Woodstock Vermont, vacation rental in Windsor

Remote Getaway near Woodstock Vermont

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Country Home next to Blow-Me-Down Covered Bridge in the Old Cornish Art Colony!, vacation rental in Windsor
Country Home next to Blow-Me-Down Covered Bridge in the Old Cornish Art Colony!, vacation rental in Windsor
Country Home next to Blow-Me-Down Covered Bridge in the Old Cornish Art Colony!, vacation rental in Windsor

Country Home next to Blow-Me-Down Covered Bridge in the Old Cornish Art Colony!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Fall & Winter Views - Rustic Contemporary Cabin on Mt Ascutney, vacation rental in Windsor
Beautiful Fall & Winter Views - Rustic Contemporary Cabin on Mt Ascutney, vacation rental in Windsor
Beautiful Fall & Winter Views - Rustic Contemporary Cabin on Mt Ascutney, vacation rental in Windsor

Beautiful Fall & Winter Views - Rustic Contemporary Cabin on Mt Ascutney

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Log manor on 65 private acres of land with entertaining amenities & hot tub, vacation rental in Windsor
Log manor on 65 private acres of land with entertaining amenities & hot tub, vacation rental in Windsor
Log manor on 65 private acres of land with entertaining amenities & hot tub, vacation rental in Windsor

Log manor on 65 private acres of land with entertaining amenities & hot tub

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Spruce Moose Cottage | Tiny House on 65 private acres, vacation rental in Windsor
Spruce Moose Cottage | Tiny House on 65 private acres, vacation rental in Windsor
Spruce Moose Cottage | Tiny House on 65 private acres, vacation rental in Windsor

Spruce Moose Cottage | Tiny House on 65 private acres

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Rockledge Farm country living, vacation rental in Windsor
Rockledge Farm country living, vacation rental in Windsor
Rockledge Farm country living, vacation rental in Windsor

Rockledge Farm country living

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Sunset Cabin - your private romantic hideaway, vacation rental in Windsor
Sunset Cabin - your private romantic hideaway, vacation rental in Windsor
Sunset Cabin - your private romantic hideaway, vacation rental in Windsor

Sunset Cabin - your private romantic hideaway

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Vermont Villa Near the Trails, vacation rental in Windsor
Vermont Villa Near the Trails, vacation rental in Windsor
Vermont Villa Near the Trails, vacation rental in Windsor

Vermont Villa Near the Trails

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Meadow View- 35 Acres outside your door, vacation rental in Windsor
Meadow View- 35 Acres outside your door, vacation rental in Windsor
Meadow View- 35 Acres outside your door, vacation rental in Windsor

Meadow View- 35 Acres outside your door

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Enjoy snowball fights or romantic nights in a 1BD vacation apartment, vacation rental in Windsor
Enjoy snowball fights or romantic nights in a 1BD vacation apartment, vacation rental in Windsor
Enjoy snowball fights or romantic nights in a 1BD vacation apartment, vacation rental in Windsor

Enjoy snowball fights or romantic nights in a 1BD vacation apartment

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Cozy Historic Hilltop Cottage with Mount Ascutney View, vacation rental in Windsor
Cozy Historic Hilltop Cottage with Mount Ascutney View, vacation rental in Windsor
Cozy Historic Hilltop Cottage with Mount Ascutney View, vacation rental in Windsor

Cozy Historic Hilltop Cottage with Mount Ascutney View

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Villa with a Fireplace Near the Trails, vacation rental in Windsor
Villa with a Fireplace Near the Trails, vacation rental in Windsor
Villa with a Fireplace Near the Trails, vacation rental in Windsor

Villa with a Fireplace Near the Trails

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Ronnoco Farm-Charming Brownsville/West Windsor, VT cottage, vacation rental in Windsor
Ronnoco Farm-Charming Brownsville/West Windsor, VT cottage, vacation rental in Windsor
Ronnoco Farm-Charming Brownsville/West Windsor, VT cottage, vacation rental in Windsor

Ronnoco Farm-Charming Brownsville/West Windsor, VT cottage

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Lovely 2 Bedroom Townhouse on Ascutney Mountain, vacation rental in Windsor
Lovely 2 Bedroom Townhouse on Ascutney Mountain, vacation rental in Windsor
Lovely 2 Bedroom Townhouse on Ascutney Mountain, vacation rental in Windsor

Lovely 2 Bedroom Townhouse on Ascutney Mountain

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Romantic Getaway or Family winter adventures in 2BD w/resort activities, vacation rental in Windsor
Romantic Getaway or Family winter adventures in 2BD w/resort activities, vacation rental in Windsor
Romantic Getaway or Family winter adventures in 2BD w/resort activities, vacation rental in Windsor

Romantic Getaway or Family winter adventures in 2BD w/resort activities

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Villa with Pool + Fitness Center Access, vacation rental in Windsor
Villa with Pool + Fitness Center Access, vacation rental in Windsor
Villa with Pool + Fitness Center Access, vacation rental in Windsor

Villa with Pool + Fitness Center Access

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Villa Near Biking and Hiking Trails, vacation rental in Windsor
Villa Near Biking and Hiking Trails, vacation rental in Windsor
Villa Near Biking and Hiking Trails, vacation rental in Windsor

Villa Near Biking and Hiking Trails

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Come spend Christmas break in Vermont, Close to skiing!, vacation rental in Windsor
Come spend Christmas break in Vermont, Close to skiing!, vacation rental in Windsor
Come spend Christmas break in Vermont, Close to skiing!, vacation rental in Windsor

Come spend Christmas break in Vermont, Close to skiing!

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
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Long Range Mountain Views in West Windsor, vacation rental in Windsor
Long Range Mountain Views in West Windsor, vacation rental in Windsor
Long Range Mountain Views in West Windsor, vacation rental in Windsor

Long Range Mountain Views in West Windsor

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Beautiful home offering privacy on 7 acres with private pond, vacation rental in Windsor
Beautiful home offering privacy on 7 acres with private pond, vacation rental in Windsor
Beautiful home offering privacy on 7 acres with private pond, vacation rental in Windsor

Beautiful home offering privacy on 7 acres with private pond

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Country living at its best, vacation rental in Windsor
Country living at its best, vacation rental in Windsor
Country living at its best, vacation rental in Windsor

Country living at its best

Holiday Rental House
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, vacation rental in Windsor
Beautiful craftsman-built home with natural wood and large windows in every room, vacation rental in Windsor
Beautiful craftsman-built home with natural wood and large windows in every room, vacation rental in Windsor

Beautiful craftsman-built home with natural wood and large windows in every room

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Inviting Vermont Home On Mount Ascutney!, vacation rental in Windsor
Inviting Vermont Home On Mount Ascutney!, vacation rental in Windsor
Inviting Vermont Home On Mount Ascutney!, vacation rental in Windsor

Inviting Vermont Home On Mount Ascutney!

Holiday Rental House
6 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Meriden Village of Plainfield Home w/ Backyard, vacation rental in Windsor
Meriden Village of Plainfield Home w/ Backyard, vacation rental in Windsor
Meriden Village of Plainfield Home w/ Backyard, vacation rental in Windsor

Meriden Village of Plainfield Home w/ Backyard

Holiday Rental House
6 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Pet-Friendly Claremont Vacation Rental!, vacation rental in Windsor
Pet-Friendly Claremont Vacation Rental!, vacation rental in Windsor
Pet-Friendly Claremont Vacation Rental!, vacation rental in Windsor

Pet-Friendly Claremont Vacation Rental!

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
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Log Cabin home with Mt Ascutney views and pool table, vacation rental in Windsor
Log Cabin home with Mt Ascutney views and pool table, vacation rental in Windsor
Log Cabin home with Mt Ascutney views and pool table, vacation rental in Windsor

Log Cabin home with Mt Ascutney views and pool table

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Luxury Vermont Vacation Rental: Private Hot Tub!, vacation rental in Windsor
Luxury Vermont Vacation Rental: Private Hot Tub!, vacation rental in Windsor
Luxury Vermont Vacation Rental: Private Hot Tub!, vacation rental in Windsor

Luxury Vermont Vacation Rental: Private Hot Tub!

Holiday Rental House
7 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Secluded Luxury Home on Huge Property with Mountain Views - Near Slopes, vacation rental in Windsor
Secluded Luxury Home on Huge Property with Mountain Views - Near Slopes, vacation rental in Windsor
Secluded Luxury Home on Huge Property with Mountain Views - Near Slopes, vacation rental in Windsor

Secluded Luxury Home on Huge Property with Mountain Views - Near Slopes

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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5 Star Accommodation Meets Farm Life #hartlandhillfarm, vacation rental in Windsor
5 Star Accommodation Meets Farm Life #hartlandhillfarm, vacation rental in Windsor
5 Star Accommodation Meets Farm Life #hartlandhillfarm, vacation rental in Windsor

5 Star Accommodation Meets Farm Life #hartlandhillfarm

Holiday Rental House
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, vacation rental in Windsor
Secluded home w/covered porch and alpine views, near ski resorts, w/foosball, vacation rental in Windsor
Secluded home w/covered porch and alpine views, near ski resorts, w/foosball, vacation rental in Windsor

Secluded home w/covered porch and alpine views, near ski resorts, w/foosball

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Rock Haven Sugar House | Field and Farm, vacation rental in Windsor
Rock Haven Sugar House | Field and Farm, vacation rental in Windsor
Rock Haven Sugar House | Field and Farm, vacation rental in Windsor

Rock Haven Sugar House | Field and Farm

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Ski-in/out, dog-friendly condo with prime location for skiing & hiking, vacation rental in Windsor
Ski-in/out, dog-friendly condo with prime location for skiing & hiking, vacation rental in Windsor
Ski-in/out, dog-friendly condo with prime location for skiing & hiking, vacation rental in Windsor

Ski-in/out, dog-friendly condo with prime location for skiing & hiking

Condo/Apartment
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Enchanting farmhouse with a picture perfect view of Mt. Ascutney, vacation rental in Windsor
Enchanting farmhouse with a picture perfect view of Mt. Ascutney, vacation rental in Windsor
Enchanting farmhouse with a picture perfect view of Mt. Ascutney, vacation rental in Windsor

Enchanting farmhouse with a picture perfect view of Mt. Ascutney

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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This cabin is a 3 bedroom(s), 3.5 bathrooms, located in West Windsor, VT., vacation rental in Windsor
This cabin is a 3 bedroom(s), 3.5 bathrooms, located in West Windsor, VT., vacation rental in Windsor
This cabin is a 3 bedroom(s), 3.5 bathrooms, located in West Windsor, VT., vacation rental in Windsor

This cabin is a 3 bedroom(s), 3.5 bathrooms, located in West Windsor, VT.

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Luxury Home, Dog Suite | Rock Haven Carriage House, vacation rental in Windsor
Luxury Home, Dog Suite | Rock Haven Carriage House, vacation rental in Windsor
Luxury Home, Dog Suite | Rock Haven Carriage House, vacation rental in Windsor

Luxury Home, Dog Suite | Rock Haven Carriage House

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Private mountain setting w/ open rooms, hiking, biking, skiing at your, vacation rental in Windsor
Private mountain setting w/ open rooms, hiking, biking, skiing at your, vacation rental in Windsor
Private mountain setting w/ open rooms, hiking, biking, skiing at your, vacation rental in Windsor

Private mountain setting w/ open rooms, hiking, biking, skiing at your

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Showing results 1-46 of 46
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