Vacation Rentals in Windsor County

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Our top choices for Windsor County vacation rentals

Interior

Addie's Place: A Quiet and Quirky Private Guesthouse

Addie's Place: A Quiet and Quirky Private Guesthouse
Hartford
10.0 out of 10, Exceptional, (5 reviews)
"Perfect size and location! "
United States
Lyn H.
The price is ￥15,093
￥29,669 total
includes taxes & fees
Feb 8 - Feb 9
Addie's Place: A Quiet and Quirky Private Guesthouse
Property grounds

Treehouse at Wise Pines- SoBo

Treehouse at Wise Pines- SoBo
Woodstock
9.8 out of 10, Exceptional, (25 reviews)
"Friendly owners with a very comfortable and accommodating space.Very well thought out with a great common space .Hiking trails , fire pit , animals , fresh eggs and produce in season.Highly recommended!!"
United States
Jo-Alice S.
The price is ￥27,514
￥34,392 total
includes taxes & fees
Feb 12 - Feb 13
Treehouse at Wise Pines- SoBo
Terrace/patio

Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Sharon
10.0 out of 10, Exceptional, (7 reviews)
"Cabin was spotless and exactly what I expected"
United States
mark g.
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Property grounds

Vermont Double Queen Suite | 10 Mins to Killington

Vermont Double Queen Suite | 10 Mins to Killington
Bridgewater
8.8 out of 10, Excellent, (5 reviews)
"This was perfect for our girls weekend! Great location, spacious & clean. Our host was so responsive & kind- highly recommend staying here when you visit Salem! "
United States
Brianna L.
The price is ￥17,923
￥37,143 total
includes taxes & fees
Feb 9 - Feb 10
Vermont Double Queen Suite | 10 Mins to Killington
Interior

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Cavendish
10.0 out of 10, Exceptional, (11 reviews)
"Super easy check in, beautiful and peaceful. Will def be back "
United States
Tyler S.
The price is ￥31,979
￥54,476 total
includes taxes & fees
Feb 8 - Feb 9
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Exterior

Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington

Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington
Plymouth
10.0 out of 10, Exceptional, (14 reviews)
"We had a great stay! Beautiful spot tucked in the woods. Great host communication!"
United States
Julie-Anne B.
The price is ￥42,449
￥104,243 total
includes taxes & fees
Feb 9 - Feb 10
Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington
Golf

Efficient condo near slopes with kitchenette & great location

Efficient condo near slopes with kitchenette & great location
Ludlow
8.6 out of 10, Excellent, (32 reviews)
"Nice place close to mountain easy in easy out"
United States
Aaron B.
The price is ￥20,281
￥40,977 total
includes taxes & fees
Feb 10 - Feb 11
Efficient condo near slopes with kitchenette & great location
Exterior

Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street

Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
Ludlow
9.0 out of 10, Wonderful, (23 reviews)
"Great rate for a place with all the basics!"
United States
Macgregor
The price is ￥19,598
￥45,062 total
includes taxes & fees
Mar 10 - Mar 11
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
Interior

King Size Master With Attached Bath,Pool Table, Open Kitchen,2 Full Baths

King Size Master With Attached Bath,Pool Table, Open Kitchen,2 Full Baths
Bethel
10.0 out of 10, Exceptional, (67 reviews)
"Very cozy, warm and inviting. Beds were all comfortable. House is big enough to have your own space yet intimate enough for pool, and family game night. Highly recommend!"
United States
Christine F.
King Size Master With Attached Bath,Pool Table, Open Kitchen,2 Full Baths
Property grounds

Gnome Home Mountain Ski Chalet w/Sauna Killington

Gnome Home Mountain Ski Chalet w/Sauna Killington
Stockbridge
10.0 out of 10, Exceptional, (4 reviews)
"Nice property in a beautiful location. Host was very responsive and informative. Thanks for the stay!"
United States
Gerald S.
The price is ￥42,544
￥89,084 total
includes taxes & fees
Feb 10 - Feb 11
Gnome Home Mountain Ski Chalet w/Sauna Killington
Exterior

Condo in the heart of town near skiing - less than a mile to Okemo Mountain

Condo in the heart of town near skiing - less than a mile to Okemo Mountain
Ludlow
9.0 out of 10, Wonderful, (14 reviews)
"Great place!"
United States
Darcie L.
The price is ￥22,325
￥51,694 total
includes taxes & fees
Feb 11 - Feb 12
Condo in the heart of town near skiing - less than a mile to Okemo Mountain
Golf

Well-appointed studio right downtown - less than a mile to Okemo Mountain

Well-appointed studio right downtown - less than a mile to Okemo Mountain
Ludlow
8.6 out of 10, Excellent, (12 reviews)
"Clean with everything we needed for a few nights stay."
United States
Sandra S.
The price is ￥20,596
￥54,565 total
includes taxes & fees
Feb 10 - Feb 11
Well-appointed studio right downtown - less than a mile to Okemo Mountain
Exterior

2nd-floor downtown Ludlow studio condo with kitchenette, streaming

2nd-floor downtown Ludlow studio condo with kitchenette, streaming
Ludlow
8.6 out of 10, Excellent, (4 reviews)
"Great location and convenient to all local businesses. I enjoyed it very much. Would stay here anytime and plan to again. "
United States
Kevin C.
The price is ￥22,168
￥48,820 total
includes taxes & fees
Feb 10 - Feb 11
2nd-floor downtown Ludlow studio condo with kitchenette, streaming
Exterior

Okemo Mt. Family Affordable 1st floor, village shuttle, walk to town, Dogs OK

Okemo Mt. Family Affordable 1st floor, village shuttle, walk to town, Dogs OK
Ludlow
9.8 out of 10, Exceptional, (173 reviews)
"Great spot to stay in with a group for skiing. Easy check in and check out process."
United States
Aidan O.
The price is ￥31,444
￥53,653 total
includes taxes & fees
Feb 8 - Feb 9
Okemo Mt. Family Affordable 1st floor, village shuttle, walk to town, Dogs OK
Smart TV, fireplace, books

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Ludlow
10.0 out of 10, Exceptional, (102 reviews)
"Ideal location, clean and comfortable condo, and kind, responsive host! The larger bedroom could benefit from blackout curtains, but if you like to wake up to bright sunlight then it's a non-issue!"
United States
Jessica C.
The price is ￥30,343
￥56,330 total
includes taxes & fees
Mar 3 - Mar 4
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Dining

Chester Farmhouse Ski Retreat near Slopes

Chester Farmhouse Ski Retreat near Slopes
Chester Depot
9.6 out of 10, Exceptional, (18 reviews)
"House was in a perfect location. The town was adorable. "
United States
Michelle A.
The price is ￥29,715
￥62,863 total
includes taxes & fees
Feb 9 - Feb 10
Chester Farmhouse Ski Retreat near Slopes
Property grounds

Large Killington Area Home | Sleeps 7 | Game Room

Large Killington Area Home | Sleeps 7 | Game Room
Bridgewater
9.6 out of 10, Exceptional, (7 reviews)
"My family enjoyed this house and there was plenty of space for sleeping and for the kids to play. Conveniently located for skiing at Killington."
United States
Owen C.
The price is ￥40,563
￥98,433 total
includes taxes & fees
Feb 9 - Feb 10
Large Killington Area Home | Sleeps 7 | Game Room
Indoor pool

Cozy Slopeside Escape - Ski-In/Out Condo at Okemo

Cozy Slopeside Escape - Ski-In/Out Condo at Okemo
Okemo Village
10.0 out of 10, Exceptional, (10 reviews)
"Location was perfect for skiing. Hosts were responsive and the stay was pleasant. Would book again."
United States
Paul T.
The price is ￥39,305
￥89,718 total
includes taxes & fees
Mar 8 - Mar 9
Cozy Slopeside Escape - Ski-In/Out Condo at Okemo
Living area

Cozy Private Cabin in Andover - Fireplace & Hot tub

Cozy Private Cabin in Andover - Fireplace & Hot tub
Andover
The price is ￥34,319
￥79,000 total
includes taxes & fees
Mar 10 - Mar 11
Cozy Private Cabin in Andover - Fireplace & Hot tub
Interior

Terrific 3-bedroom cottage with AC in charming Cavendish

Terrific 3-bedroom cottage with AC in charming Cavendish
Cavendish
The price is ￥35,375
￥95,615 total
includes taxes & fees
Feb 9 - Feb 10
Terrific 3-bedroom cottage with AC in charming Cavendish
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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Top Windsor County Hotel Reviews

The Hartness House

The Hartness House

10/10 Excellent
"We really liked the house. Auto check in was convenient. Front lobby and common area is nice and cozy. "
Sandra 1-night trip
Posted 1 day ago
The Hartness House

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Vacation Apartments in Windsor County

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