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Windsor Vacation Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
48 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

Rental Home
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!

Rental Home
1 bedroom
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!

Rental Home
1 bedroom
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

Rental Home
1 bedroom
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!

Rental Home
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Private Wing of largest Colonial Revival Mansion- Only 15 min to Woodstock, vacation rental in Windsor
Private Wing of largest Colonial Revival Mansion- Only 15 min to Woodstock, vacation rental in Windsor
Private Wing of largest Colonial Revival Mansion- Only 15 min to Woodstock, vacation rental in Windsor

Private Wing of largest Colonial Revival Mansion- Only 15 min to Woodstock

Rental Home
3 bedrooms
0 bathrooms
Sleeps 7
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!

Rental Home
2 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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 3
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

Rental Home
3 bedrooms
4 bathrooms
Sleeps 3
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

Rental Home
16 bedrooms
19 bathrooms
Sleeps 16
Match: Sleeps
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Largest Colonial Revival Mansion less than 15 minutes to Woodstock, vacation rental in Windsor
Largest Colonial Revival Mansion less than 15 minutes to Woodstock, vacation rental in Windsor
Largest Colonial Revival Mansion less than 15 minutes to Woodstock, vacation rental in Windsor

Largest Colonial Revival Mansion less than 15 minutes to Woodstock

Rental Home
15 bedrooms
15 bathrooms
Sleeps 15
Match: Sleeps
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The following properties within 20 miles of Windsor match all your filters:
Amazing cabin on 12 acres with AC, jetted tub & woodstove - dog-friendly, vacation rental in Windsor
Amazing cabin on 12 acres with AC, jetted tub & woodstove - dog-friendly, vacation rental in Windsor
Amazing cabin on 12 acres with AC, jetted tub & woodstove - dog-friendly, vacation rental in Windsor

Amazing cabin on 12 acres with AC, jetted tub & woodstove - dog-friendly

Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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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 3
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

Rental Home
3 bedrooms
3 bathrooms
Sleeps 3
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!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 3
Match: Sleeps
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Exquisite Log Home with views near Woodstock, Vermont, vacation rental in Windsor
Exquisite Log Home with views near Woodstock, Vermont, vacation rental in Windsor
Exquisite Log Home with views near Woodstock, Vermont, vacation rental in Windsor

Exquisite Log Home with views near Woodstock, Vermont

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Village Farmhouse - Okemo, Ascutney, Green Mountain Horse Assoc. Pet-friendly., vacation rental in Windsor
Village Farmhouse - Okemo, Ascutney, Green Mountain Horse Assoc. Pet-friendly., vacation rental in Windsor
Village Farmhouse - Okemo, Ascutney, Green Mountain Horse Assoc. Pet-friendly., vacation rental in Windsor

Village Farmhouse - Okemo, Ascutney, Green Mountain Horse Assoc. Pet-friendly.

Rental Home
4 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Cozy Historic Hilltop Cottage, vacation rental in Windsor
Cozy Historic Hilltop Cottage, vacation rental in Windsor
Cozy Historic Hilltop Cottage, vacation rental in Windsor

Cozy Historic Hilltop Cottage

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Mt Ascutney Custom Home With Mountain Views, vacation rental in Windsor
Mt Ascutney Custom Home With Mountain Views, vacation rental in Windsor
Mt Ascutney Custom Home With Mountain Views, vacation rental in Windsor

Mt Ascutney Custom Home With Mountain Views

Rental Home
2 bedrooms
2 bathrooms
Sleeps 2
Match: Sleeps
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Spruce Moose Lodge | Log Manor on 65 private acres, vacation rental in Windsor
Spruce Moose Lodge | Log Manor on 65 private acres, vacation rental in Windsor
Spruce Moose Lodge | Log Manor on 65 private acres, vacation rental in Windsor

Spruce Moose Lodge | Log Manor on 65 private acres

Rental Home
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

Condo/Apartment
0 bedrooms
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

Rental Home
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

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Holiday Inn Mount Ascutney Resort -1BD Sleeps 4, vacation rental in Windsor
Holiday Inn Mount Ascutney Resort -1BD Sleeps 4, vacation rental in Windsor
Holiday Inn Mount Ascutney Resort -1BD Sleeps 4, vacation rental in Windsor

Holiday Inn Mount Ascutney Resort -1BD Sleeps 4

Rental Home
1 bedroom
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

Rental Home
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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A Beautiful  Two Bedroom Mountainside Escape in Vermont, vacation rental in Windsor
A Beautiful  Two Bedroom Mountainside Escape in Vermont, vacation rental in Windsor
A Beautiful  Two Bedroom Mountainside Escape in Vermont, vacation rental in Windsor

A Beautiful Two Bedroom Mountainside Escape in Vermont

Rental Home
2 bedrooms
2 bathrooms
Sleeps 2
Match: Sleeps
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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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 2
Match: Sleeps
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Unique home with woodstove, AC, W/D, Sears & Roebuck kitchen - dog-friendly, vacation rental in Windsor
Unique home with woodstove, AC, W/D, Sears & Roebuck kitchen - dog-friendly, vacation rental in Windsor
Unique home with woodstove, AC, W/D, Sears & Roebuck kitchen - dog-friendly, vacation rental in Windsor

Unique home with woodstove, AC, W/D, Sears & Roebuck kitchen - dog-friendly

Rental Home
2 bedrooms
2 bathrooms
Sleeps 2
Match: Sleeps
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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

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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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

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

Romantic Getaway or Family winter adventures in 2BD with resort activities

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Village Farmhouse - mins to GMHA, Okemo, Killington. Pet-friendly., vacation rental in Windsor
Village Farmhouse - mins to GMHA, Okemo, Killington. Pet-friendly., vacation rental in Windsor
Village Farmhouse - mins to GMHA, Okemo, Killington. Pet-friendly., vacation rental in Windsor

Village Farmhouse - mins to GMHA, Okemo, Killington. Pet-friendly.

Rental Home
4 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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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

Rental Home
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

Rental Home
3 bedrooms
3 bathrooms
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

Rental Home
3 bedrooms
3 bathrooms
Sleeps 3
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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 3
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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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A Quiet Retreat in Rural New Hampshire, vacation rental in Windsor
A Quiet Retreat in Rural New Hampshire, vacation rental in Windsor
A Quiet Retreat in Rural New Hampshire, vacation rental in Windsor

A Quiet Retreat in Rural New Hampshire

Rental Home
3 bedrooms
3 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

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

Inviting Vermont Cabin On Mount Ascutney!

Rental Home
4 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Meriden Village of Plainfield Home w/ Grill!, vacation rental in Windsor
Meriden Village of Plainfield Home w/ Grill!, vacation rental in Windsor
Meriden Village of Plainfield Home w/ Grill!, vacation rental in Windsor

Meriden Village of Plainfield Home w/ Grill!

Rental Home
5 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!

Rental Home
5 bedrooms
2 bathrooms
Sleeps 5
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

Rental Home
4 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!

Rental Home
4 bedrooms
4 bathrooms
Sleeps 4
Match: Sleeps
More info
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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

Rental Home
5 bedrooms
4 bathrooms
Sleeps 5
Match: Sleeps
More info
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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

Rental Home
5 bedrooms
7 bathrooms
Sleeps 12
Match: Sleeps
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Chase House Inn - Edwin Stanton Room, vacation rental in Windsor
Chase House Inn - Edwin Stanton Room, vacation rental in Windsor
Chase House Inn - Edwin Stanton Room, vacation rental in Windsor

Chase House Inn - Edwin Stanton Room

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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A Quiet Retreat in Rural New Hampshire, vacation rental in Windsor
A Quiet Retreat in Rural New Hampshire, vacation rental in Windsor
A Quiet Retreat in Rural New Hampshire, vacation rental in Windsor

A Quiet Retreat in Rural New Hampshire

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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