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Windsor Holiday Rentals

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50 rentals in Windsor.
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Stunning Modern Cabin on Beautiful Vermont Farm, holiday rental in Windsor

Stunning Modern Cabin on Beautiful Vermont Farm

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Vermont cabin on 20 acres in open field, holiday rental in Windsor

Vermont cabin on 20 acres in open field

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!, holiday rental in Windsor

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

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Beautiful Views Overlooking Quechee, holiday rental in Windsor

Beautiful Views Overlooking Quechee

3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Vacation/Travelers Apartment At Clay Hill Corners Blueberry Farm, holiday rental in Windsor

Vacation/Travelers Apartment At Clay Hill Corners Blueberry Farm

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Luxury Mountain Home Featuring 2 Master Suites and Spectacular Views!, holiday rental in Windsor

Luxury Mountain Home Featuring 2 Master Suites and Spectacular Views!

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful craftsman-built home with natural wood and large windows in every room, holiday rental in Windsor

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

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Secluded Get Away Retreat, holiday rental in Windsor

Secluded Get Away Retreat

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Meadow View- 35 Acres outside your door, holiday rental in Windsor

Meadow View- 35 Acres outside your door

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Woodstock Village Carriage House, holiday rental in Windsor

Woodstock Village Carriage House

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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The Real Vermont All Seasons Get-Away Home - Part of Queche Lakes Country Club, holiday rental in Windsor

The Real Vermont All Seasons Get-Away Home - Part of Queche Lakes Country Club

3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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5 Bedroom Home with Views of Quechee, holiday rental in Windsor

5 Bedroom Home with Views of Quechee

5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Historic Ski Lodge on 112-Acre Vineyard, holiday rental in Windsor

Historic Ski Lodge on 112-Acre Vineyard

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Secluded, deluxe home with mountain view - close to hiking, skiing, & fishing, holiday rental in Windsor

Secluded, deluxe home with mountain view - close to hiking, skiing, & fishing

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Rockledge Farm country living, holiday rental in Windsor

Rockledge Farm country living

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Beautiful Single Family Condominium in Award-Winning Eastman Community, holiday rental in Windsor

Beautiful Single Family Condominium in Award-Winning Eastman Community

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Charming 3 bedroom house on the golf course, holiday rental in Windsor

Charming 3 bedroom house on the golf course

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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A charming 1820's farmhouse, ideally situated four miles from the Woodstock Gree, holiday rental in Windsor

A charming 1820's farmhouse, ideally situated four miles from the Woodstock Gree

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful 6 Bedroom Quechee Vermont 4 Season Vacation Destination, holiday rental in Windsor

Beautiful 6 Bedroom Quechee Vermont 4 Season Vacation Destination

6 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Spectacular  Views At This Luxury Country Estate, Walking Distance To Town, holiday rental in Windsor

Spectacular Views At This Luxury Country Estate, Walking Distance To Town

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Quechee Condo - Affordable Vacation Resort ~Ski/Golf/Tennis/Lake/Pool/Gym, holiday rental in Windsor

Quechee Condo - Affordable Vacation Resort ~Ski/Golf/Tennis/Lake/Pool/Gym

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Large Historic Home w/6 Bedrooms and 6.5 baths-On River, w/ Hot Tub, holiday rental in Windsor

Large Historic Home w/6 Bedrooms and 6.5 baths-On River, w/ Hot Tub

6 bedrooms
6 bathrooms
Sleeps 15
Match: Sleeps
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2 Bedroom Condo in Quechee, ~VT~ - a Four Season Community!, holiday rental in Windsor

2 Bedroom Condo in Quechee, ~VT~ - a Four Season Community!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Skiing or Getting Away from it All? This House is what you need., holiday rental in Windsor

Skiing or Getting Away from it All? This House is what you need.

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Villa with Pool + Fitness Center Access! | Awesome Location Near the Trails, holiday rental in Windsor

Villa with Pool + Fitness Center Access! | Awesome Location Near the Trails

3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Splendid 1920s Vermont Farmhouse, holiday rental in Windsor

Splendid 1920s Vermont Farmhouse

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Classic Vermont home w/hot tub, deck & wood stove-near Okemo Mountain Resort, holiday rental in Windsor

Classic Vermont home w/hot tub, deck & wood stove-near Okemo Mountain Resort

3 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Quechee Lakes Hilltop Condo; End Unit Immaculately Maintained, holiday rental in Windsor

Quechee Lakes Hilltop Condo; End Unit Immaculately Maintained

3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Villa with a Fireplace Near the Trails | Pool + Fitness Center Access!, holiday rental in Windsor

Villa with a Fireplace Near the Trails | Pool + Fitness Center Access!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Blue Forest Farm Estate - Extraordinary 326 Acres with Two Separate Rentals!, holiday rental in Windsor

Blue Forest Farm Estate - Extraordinary 326 Acres with Two Separate Rentals!

6 bedrooms
6 bathrooms
Sleeps 15
Match: Sleeps
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Little Cabin Retreat - *Dog Friendly*, holiday rental in Windsor

Little Cabin Retreat - *Dog Friendly*

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Village Farmhouse - mins to GMHA, Okemo, Killington. Pet-friendly., holiday rental in Windsor

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

4 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Quechee at its Finest!, holiday rental in Windsor

Quechee at its Finest!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Reading Farms Estate/ Vermont Luxury Rental, holiday rental in Windsor

Reading Farms Estate/ Vermont Luxury Rental

15 bedrooms
12 bathrooms
Sleeps 46
Match: Sleeps
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25 Acre Mtn Playground, 2 Bd, Great Ski Access, Close to Okemo, VAST trails, holiday rental in Windsor

25 Acre Mtn Playground, 2 Bd, Great Ski Access, Close to Okemo, VAST trails

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Quechee Vermont Vacation Home-Ideal for Families, holiday rental in Windsor

Quechee Vermont Vacation Home-Ideal for Families

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Private Country Cabin - Close to Skiing and Snowmobiling, holiday rental in Windsor

Private Country Cabin - Close to Skiing and Snowmobiling

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Modern Cabin on a Vermont Farm - Stunning Panoramic Views!, holiday rental in Windsor

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

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Close to Okemo, 25 Acre Mtn Playground, 2 Bd, Great Ski Access, VAST trails, holiday rental in Windsor

Close to Okemo, 25 Acre Mtn Playground, 2 Bd, Great Ski Access, VAST trails

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Cozy Historic Hilltop Cottage, holiday rental in Windsor

Cozy Historic Hilltop Cottage

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Feel at Home in the Little Red Cabin! Less than 15 min to Okemo!, holiday rental in Windsor

Feel at Home in the Little Red Cabin! Less than 15 min to Okemo!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - The Perch, holiday rental in Windsor

Tentrr Signature Site - The Perch

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - The Perch, holiday rental in Windsor

Tentrr Signature Site - The Perch

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - Ascutney View, holiday rental in Windsor

Tentrr Signature Site - Ascutney View

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Xanadu - Modern House Perfect for Group Getaways, holiday rental in Windsor

Xanadu - Modern House Perfect for Group Getaways

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Guest House at Blue Forest Farm Estate - Spectacular 326 Acre Estate!, holiday rental in Windsor

Guest House at Blue Forest Farm Estate - Spectacular 326 Acre Estate!

4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Serene Vermont Retreat, holiday rental in Windsor

Serene Vermont Retreat

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Chase House Inn - Edwin Stanton Room, holiday rental in Windsor

Chase House Inn - Edwin Stanton Room

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Cute VT Bungalow With 180 Degree View of NH, holiday rental in Windsor

Cute VT Bungalow With 180 Degree View of NH

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Newport NH Sunapee Lake/Ski Area - Cozy Cottage, holiday rental in Windsor

Newport NH Sunapee Lake/Ski Area - Cozy Cottage

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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