Cottages in Windsor County

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Check prices for these dates

Next weekend
27 Jun - 29 Jun
In two weeks
4 Jul - 6 Jul
In one month
18 Jul - 20 Jul
In two months
15 Aug - 17 Aug

Featured Cottages in Windsor County

Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!
Interior

Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!

3.0 star property
Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!
Lovely Ludlow Farmhouse ~ 1 Mi to Town & Slopes!
Interior

Lovely Ludlow Farmhouse ~ 1 Mi to Town & Slopes!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Great place "
Lovely Ludlow Farmhouse ~ 1 Mi to Town & Slopes!
18 Mi to Skiing: Colorful Home in Springfield!
Interior

18 Mi to Skiing: Colorful Home in Springfield!

3.0 star property
18 Mi to Skiing: Colorful Home in Springfield!
Picture-perfect Vermont Mtn Cabin w/ Hot Tub!
Private kitchen

Picture-perfect Vermont Mtn Cabin w/ Hot Tub!

3.0 star property
Picture-perfect Vermont Mtn Cabin w/ Hot Tub!
Inviting Vermont Home On Mount Ascutney!
Interior

Inviting Vermont Home On Mount Ascutney!

3.0 star property
Inviting Vermont Home On Mount Ascutney!
Chester Farmhouse on 100 Acres, 15 Min to Okemo!
Interior

Chester Farmhouse on 100 Acres, 15 Min to Okemo!

3.0 star property
Chester Farmhouse on 100 Acres, 15 Min to Okemo!
Killington Area Escape w/ Deck, Views & Hot Tub!
Interior

Killington Area Escape w/ Deck, Views & Hot Tub!

3.0 star property
Killington Area Escape w/ Deck, Views & Hot Tub!
Luxury Vermont Vacation Rental: Private Hot Tub!
Private kitchen

Luxury Vermont Vacation Rental: Private Hot Tub!

3.0 star property
Luxury Vermont Vacation Rental: Private Hot Tub!
Weston Vacation Rental - Close to Ski Resorts!
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Weston Vacation Rental - Close to Ski Resorts!

3.0 star property
Weston Vacation Rental - Close to Ski Resorts!
Peaceful Cavendish Retreat w/ Hot Tub & Fireplace!
Outdoor dining

Peaceful Cavendish Retreat w/ Hot Tub & Fireplace!

3.0 star property
Peaceful Cavendish Retreat w/ Hot Tub & Fireplace!
Swim, Ski & Sip: Lakefront Retreat in Plymouth
Interior

Swim, Ski & Sip: Lakefront Retreat in Plymouth

3.0 star property
Swim, Ski & Sip: Lakefront Retreat in Plymouth
Family-friendly Ludlow Cabin on Lake Pauline!
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Family-friendly Ludlow Cabin on Lake Pauline!

3.0 star property
Family-friendly Ludlow Cabin on Lake Pauline!
17-acre Vermont Escape w/ Panoramic Mountain Views
Interior

17-acre Vermont Escape w/ Panoramic Mountain Views

3.0 star property
17-acre Vermont Escape w/ Panoramic Mountain Views
Cozy Okemo Cabin: Steps to Lake, 2 Mi to Slopes!
Interior

Cozy Okemo Cabin: Steps to Lake, 2 Mi to Slopes!

3.0 star property
Cozy Okemo Cabin: Steps to Lake, 2 Mi to Slopes!
Remote Escape: Vermont Cabin w/ Mountaintop Views!
Property grounds

Remote Escape: Vermont Cabin w/ Mountaintop Views!

2.0 star property
Remote Escape: Vermont Cabin w/ Mountaintop Views!
Vermont Mountain Retreat: The Antler House
Interior

Vermont Mountain Retreat: The Antler House

3.0 star property
Vermont Mountain Retreat: The Antler House
Ludlow Home w/ Hot Tub, Near Okemo Resort!
Interior

Ludlow Home w/ Hot Tub, Near Okemo Resort!

3.0 star property
Ludlow Home w/ Hot Tub, Near Okemo Resort!
Hike, Ski & Unwind: Cabin w/ Deck in Chester!
Interior

Hike, Ski & Unwind: Cabin w/ Deck in Chester!

3.0 star property
Hike, Ski & Unwind: Cabin w/ Deck in Chester!
Hot Tub, Fire Pit & Grill: Remote Springfield Home
Interior

Hot Tub, Fire Pit & Grill: Remote Springfield Home

3.0 star property
Hot Tub, Fire Pit & Grill: Remote Springfield Home
Near Okemo Slopes: Peaceful Home w/ Trail Access
Interior

Near Okemo Slopes: Peaceful Home w/ Trail Access

3.0 star property
Near Okemo Slopes: Peaceful Home w/ Trail Access
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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