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Vacation Rentals in Windsor County

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Our top choices for Windsor County vacation rentals

1. Perfect Getaway! Cozy, Modern & Convenience to Everything!

Perfect Getaway! Cozy, Modern & Convenience to Everything!
Ludlow
9.8 out of 10, Exceptional, (86 reviews)
"Great place to stay, very easy to get to. A cozy and comfortable place, that is always clean. There are postings and labels throughout, which is very helpful. Hosts are great and make the experience very easy. Oh and the bed is amazing!!"
United States
Vanessa W.
The price is ¥16,130
¥21,829 total
includes taxes & fees
Aug 15 - Aug 16
Perfect Getaway! Cozy, Modern & Convenience to Everything!

2. 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, (13 reviews)
"Very welcoming, awesome weekend getaway."
United States
Zachary B.
The price is ¥23,921
¥50,903 total
includes taxes & fees
Sep 7 - Sep 8
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

3. Addie's Place: A Quiet and Quirky Guesthouse

Addie's Place: A Quiet and Quirky Guesthouse
Hartford
9.4 out of 10, Exceptional, (15 reviews)
"Nice cottage setting in a quiet neighborhood, my dogs loved it!"
United States
Victor R.
The price is ¥23,921
¥41,267 total
includes taxes & fees
Aug 20 - Aug 21
Addie's Place: A Quiet and Quirky Guesthouse

4. Fat Sheep Farm & Cabins

Fat Sheep Farm & Cabins
3.0 star property
Windsor
9.8 out of 10, Exceptional, (13 reviews)
"Woman who runs the place is great, such a nice little cabin beautiful views! "
United States
Jessica
The price is ¥30,381
¥41,807 total
includes taxes & fees
Sep 1 - Sep 2
Fat Sheep Farm & Cabins

5. 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, (23 reviews)
"We had a great stay. The hot tub was perfect after a long day of skiing."
United States
Michael L.
The price is ¥27,413
¥49,093 total
includes taxes & fees
Aug 19 - Aug 20
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

6. Beautiful 3-bedroom house with AC in charming Bridgewater

Beautiful 3-bedroom house with AC in charming Bridgewater
Bridgewater
10.0 out of 10, Exceptional, (1 review)
"Great house with fun decorations. Comfortable with lots of room; full kitchen with ample dining area. Loved the coffee available and the sound machine in the bedroom- great conveniences! Communication around booking were great with easy check in and check out."
United States
Susan S.
The price is ¥34,764
¥87,159 total
includes taxes & fees
Sep 14 - Sep 15
Beautiful 3-bedroom house with AC in charming Bridgewater

7. Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Clock Tower Base Area
9.2 out of 10, Wonderful, (30 reviews)
"The slope side condo was wonderful, warm and had everything we needed. Thank you, Amy"
United States
AMY K.
The price is ¥8,205
¥37,013 total
includes taxes & fees
Sep 9 - Sep 10
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

8. 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
9.8 out of 10, Exceptional, (109 reviews)
"Great location right in town and close to Okemo."
United States
Justin P.
The price is ¥30,618
¥65,024 total
includes taxes & fees
Sep 14 - Sep 15
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

9. Cozy Studio Condo with Great Location, WiFi & Kitchenette

Cozy Studio Condo with Great Location, WiFi & Kitchenette
Ludlow
8.6 out of 10, Excellent, (32 reviews)
"Small but well organized and super convenient!"
United States
Mikhail R.
The price is ¥15,899
¥38,041 total
includes taxes & fees
Sep 12 - Sep 13
Cozy Studio Condo with Great Location, WiFi & Kitchenette

10. 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, (26 reviews)
"Great location - walkable to small town. Very close drive to slopes"
United States
Keath
The price is ¥16,736
¥43,260 total
includes taxes & fees
Aug 16 - Aug 17
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street

11. Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck

Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck
Plymouth
9.8 out of 10, Exceptional, (24 reviews)
"convenient to okemo"
United States
marcus l.
The price is ¥29,303
¥109,585 total
includes taxes & fees
Aug 23 - Aug 24
Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck

12. Okemo Mountain, Family Affordable 2 fl village walk to town, Dogs OK.fireplace.

Okemo Mountain, Family Affordable 2 fl village walk to town, Dogs OK.fireplace.
Ludlow
9.8 out of 10, Exceptional, (16 reviews)
"Great stay, house is clean and has everything you’de ever need. Perfect location to explore the ludlow area. Thanks Bob, we enjoyed ourselves "
United States
Tyler
The price is ¥21,528
¥41,266 total
includes taxes & fees
Aug 18 - Aug 19
Okemo Mountain, Family Affordable 2 fl village walk to town, Dogs OK.fireplace.

13. Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Ludlow
The price is ¥8,875
¥46,164 total
includes taxes & fees
Aug 17 - Aug 18
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

14. Ski-In/Out Condo with Mountain Views, and Washer/Dryer

Ski-In/Out Condo with Mountain Views, and Washer/Dryer
Ludlow
9.6 out of 10, Exceptional, (18 reviews)
"Very clean and comfortable for our family of 4. Great ski-in/ski-out location - easily accessible to all lifts. Highly recommend. "
United States
Carey S.
The price is ¥21,935
¥70,302 total
includes taxes & fees
Sep 9 - Sep 10
Ski-In/Out Condo with Mountain Views, and Washer/Dryer

15. Efficient condo near slopes with kitchenette & great location

Efficient condo near slopes with kitchenette & great location
Ludlow
8.6 out of 10, Excellent, (33 reviews)
"the home was clean and very nice. "
United States
Frank R.
The price is ¥15,899
¥36,961 total
includes taxes & fees
Sep 12 - Sep 13
Efficient condo near slopes with kitchenette & great location

16. Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit

Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
3.0 star property
Ludlow
The price is ¥41,282
¥66,858 total
includes taxes & fees
Sep 11 - Sep 12
Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit

17. Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock

Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
Stockbridge
10.0 out of 10, Exceptional, (3 reviews)
"Exactly as pictured, specious, clean. Owners were extremely responsive and kind."
United States
Sophie L.
The price is ¥21,224
¥93,665 total
includes taxes & fees
Aug 16 - Aug 17
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock

18. Ski Home/Arcade Mountain Views Near Killington/Woodstock

Ski Home/Arcade Mountain Views Near Killington/Woodstock
Stockbridge
10.0 out of 10, Exceptional, (3 reviews)
"Skied Killington for 2 days and was a 20 min drive. Fun to drive the 100."
United States
Kevin M.
The price is ¥21,224
¥93,665 total
includes taxes & fees
Aug 16 - Aug 17
Ski Home/Arcade Mountain Views Near Killington/Woodstock

19. Terrific 3-bedroom cottage with AC in charming Cavendish

Terrific 3-bedroom cottage with AC in charming Cavendish
Cavendish
10.0 out of 10, Exceptional, (2 reviews)
"Such a beautiful place and we loved the area. It was our first trip to Vermont. "
United States
Mark G.
The price is ¥35,881
¥96,984 total
includes taxes & fees
Aug 17 - Aug 18
Terrific 3-bedroom cottage with AC in charming Cavendish

20. Stylish Designer Loft And Adventure Hub With EV Charger Near Woodstock & Okemo

Stylish Designer Loft And Adventure Hub With EV Charger Near Woodstock & Okemo
West Windsor
10.0 out of 10, Exceptional, (1 review)
"Yes, our stay was very nice! Beautiful cabin, very clean ! "
United States
Alicja
Stylish Designer Loft And Adventure Hub With EV Charger Near Woodstock & Okemo
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

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Vacation Apartments in Windsor County

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