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Windsor Vacation Rentals

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50 rentals in Windsor.
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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

Rental Home
1 bedroom
1 bathroom
Sleeps 4
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Vermont cabin on 20 acres in open field

Rental Home
2 bedrooms
1 bathroom
Sleeps 5
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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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Scenic South Woodstock, Vermont home

Rental Home
4 bedrooms
3 bathrooms
Sleeps 6
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Woodstock Farmhouse Completely Updated Close to Town & Ski Areas

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Panoramic Mountain View, Lots To Do, Or Enjoy Doing Nothing

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Vacation/Travelers Apartment At Clay Hill Corners Blueberry Farm

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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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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Idyllic: c.1842 farmhouse on 26 acres with breathtaking view of the mountains

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
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Cozy Historic Hilltop Cottage with Mount Ascutney View

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Meadow View- 35 Acres outside your door

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Secluded Get Away Retreat

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Country Home next to Blow-Me-Down Covered Bridge in the Old Cornish Art Colony!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Dog Friendly Home in S. Woodstock

Rental Home
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Village Farmhouse - Okemo, Ascutney, Green Mountain Horse Assoc. Pet-friendly.

Rental Home
4 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Beautiful Guest House Set Among the Trees

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
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The Real Vermont All Seasons Get-Away Home - Part of Queche Lakes Country Club

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Secluded, deluxe home with mountain view - close to hiking, skiing, & fishing

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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New to VRBO Fully Renovated and Furnished Home on Quechee Lakes Golf Courses

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Sunset Cabin - your private romantic hideaway

Rental Home
1 bedroom
1 bathroom
Sleeps 2
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Exquisite Log Home with views near Woodstock, Vt.

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
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Spectacular Views At This Luxury Country Estate, Walking Distance To Town

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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NEW! Available Sept. 11. Long Range Mountain Views in West Windsor

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
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5 Star Accommodation Meets Farm Life #hartlandhillfarm

Rental Home
5 bedrooms
7 bathrooms
Sleeps 12
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NEW LISTING! Hartland Bungalow

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Splendid 1920s Vermont Farmhouse

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Remote Getaway in Southern Vermont

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Classic Vermont home w/hot tub, deck & wood stove-near Okemo Mountain Resort

Rental Home
3 bedrooms
2 bathrooms
Sleeps 13
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Riverside Retreat w/Deck by Cornish-Windsor Bridge

Rental Home
6 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Blue Forest Farm Estate - Extraordinary 326 Acres with Two Separate Rentals!

Rental Home
6 bedrooms
6 bathrooms
Sleeps 15
Match: Sleeps
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Luxury 4 Bedroom / 3.5 Bath Private Home with Enclosed Porch & Game Room

Rental Home
4 bedrooms
4 bathrooms
Sleeps 12
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Village Farmhouse - mins to GMHA, Okemo, Killington. Pet-friendly.

Rental Home
4 bedrooms
1 bathroom
Sleeps 8
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NEW! - 2 Bedroom / 1 Bath Riverside Cottage

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Reading Farms Estate/ Vermont Luxury Rental

Rental Home
15 bedrooms
12 bathrooms
Sleeps 46
Match: Sleeps
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Havenwood, a beautiful private, gated estate in Woodstock, Vermont

Rental Home
7 bedrooms
8 bathrooms
Sleeps 14
Match: Sleeps
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Beautiful Modern Cabin on a Vermont Farm - Stunning Panoramic Views!

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Cozy Historic Hilltop Cottage

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - The Perch

Rental Home
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - The Perch

Rental Home
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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* NEW! The Cottage at Reading Farms Estate

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Tentrr Signature Site - Ascutney View

Rental Home
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - Ascutney View

Rental Home
0 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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* NEW in 2019! All inclusive 400 acre resort estate

Rental Home
8 bedrooms
10 bathrooms
Sleeps 20
Match: Sleeps
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* NEW!! The BARN at Reading Farms Estate

Rental Home
3 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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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
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Guest House at Blue Forest Farm Estate - Spectacular 326 Acre Estate!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Serene Vermont Retreat

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Chase House Inn - Edwin Stanton Room

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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1820 House

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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