A river flowing through a forest with autumn foliage.

Windsor County Holiday Rentals

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Our top choices for Windsor County holiday rentals

Interior

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

Addie's Place: A Quiet and Quirky Guesthouse
Hartford
9.6 out of 10, Exceptional, (18 reviews)
"Perfect size and location! "
United States
Lyn H.
The price is HK$1,000
HK$1,803 total
includes taxes & fees
9 Sept - 10 Sept
Addie's Place: A Quiet and Quirky Guesthouse
Exterior

2. 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 HK$1,524
HK$2,089 total
includes taxes & fees
10 Sept - 11 Sept
Fat Sheep Farm & Cabins
Living area

3. Luxury Adventure Cabin #2—Kayaks, Trails, Lakes & 24/7 Hot Tub Access

Luxury Adventure Cabin #2—Kayaks, Trails, Lakes & 24/7 Hot Tub Access
Cavendish
10.0 out of 10, Exceptional, (27 reviews)
"We had a great stay. The hot tub was perfect after a long day of skiing."
United States
Michael L.
The price is HK$1,372
HK$2,913 total
includes taxes & fees
9 Sept - 10 Sept
Luxury Adventure Cabin #2—Kayaks, Trails, Lakes & 24/7 Hot Tub Access
Terrace/patio

4. 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, (15 reviews)
"That was the most beautiful stay that we’ve had in a long time. Everything was absolutely perfect. We will definitely be back."
United States
Kaity F.
The price is HK$1,254
HK$2,582 total
includes taxes & fees
20 Sept - 21 Sept
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Property grounds

5. Bridgewater Living - Woodstock Suite

Bridgewater Living - Woodstock Suite
Bridgewater
The price is HK$941
HK$1,809 total
includes taxes & fees
9 Sept - 10 Sept
Bridgewater Living - Woodstock Suite
Living area

6. 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 HK$403
HK$1,820 total
includes taxes & fees
9 Sept - 10 Sept
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Property grounds

7. Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Clock Tower Base Area
8.8 out of 10, Excellent, (81 reviews)
"Lots of steps but great space. Blankets were dirty, which was the only downside. "
United States
serena m.
The price is HK$585
HK$2,088 total
includes taxes & fees
9 Sept - 10 Sept
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Property grounds

8. 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, (2 reviews)
"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 HK$1,254
HK$3,715 total
includes taxes & fees
9 Sept - 10 Sept
Beautiful 3-bedroom house with AC in charming Bridgewater
Living area

9. 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 HK$1,029
HK$3,349 total
includes taxes & fees
9 Sept - 10 Sept
Ski-In/Out Condo with Mountain Views, and Washer/Dryer
Living area

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

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Ludlow
The price is HK$436
HK$2,323 total
includes taxes & fees
30 Sept - 1 Oct
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Beach

11. Cabin on the hill Ascutney Vt - 4 bedrooms

Cabin on the hill Ascutney Vt - 4 bedrooms
West Windsor
10.0 out of 10, Exceptional, (1 review)
"The Cabin in the Woods looks very rustic on the outside, but a cabin ine the woods should. Inside was a pleasant surprise. Full kitchen, large leather wrap around sofa to watch the LARGE flat-screen TV, large dining room table, 4 bedrooms, and 2 full baths made this a perfect get away place."
United States
Alvin
The price is HK$2,187
HK$4,084 total
includes taxes & fees
10 Sept - 11 Sept
Cabin on the hill Ascutney Vt - 4 bedrooms
Interior

12. 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 HK$1,183
HK$4,717 total
includes taxes & fees
9 Sept - 10 Sept
Ski Home/Arcade Mountain Views Near Killington/Woodstock
Living area

13. 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 HK$1,441
HK$5,370 total
includes taxes & fees
9 Sept - 10 Sept
Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck
Exterior

14. 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 HK$1,411
HK$2,480 total
includes taxes & fees
17 Sept - 18 Sept
Okemo Mountain, Family Affordable 2 fl village walk to town, Dogs OK.fireplace.
Exterior

15. 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 HK$1,183
HK$4,778 total
includes taxes & fees
9 Sept - 10 Sept
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
Golf

16. 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
8.8 out of 10, Excellent, (13 reviews)
"This place was so close to Okemo, and walking distance to the local pub and restaurants."
United States
Brian
The price is HK$782
HK$2,420 total
includes taxes & fees
20 Sept - 21 Sept
Well-appointed studio right downtown - less than a mile to Okemo Mountain
Golf

17. 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 HK$782
HK$1,818 total
includes taxes & fees
18 Sept - 19 Sept
Efficient condo near slopes with kitchenette & great location
Exterior

18. 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 HK$782
HK$2,066 total
includes taxes & fees
21 Sept - 22 Sept
2nd-floor downtown Ludlow studio condo with kitchenette, streaming
Living area

19. 2-BD short drive to DHMC & Dartmouth College

2-BD short drive to DHMC & Dartmouth College
Sharon
The price is HK$1,490
HK$2,415 total
includes taxes & fees
22 Sept - 23 Sept
2-BD short drive to DHMC & Dartmouth College
Property grounds

20. Gnome Home Mountain Ski Chalet w/Sauna Killington

Gnome Home Mountain Ski Chalet w/Sauna Killington
Stockbridge
10.0 out of 10, Exceptional, (5 reviews)
"Nice property in a beautiful location. Host was very responsive and informative. Thanks for the stay!"
United States
Gerald S.
The price is HK$1,725
HK$3,949 total
includes taxes & fees
15 Sept - 16 Sept
Gnome Home Mountain Ski Chalet w/Sauna Killington
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 Quechee Inn at Marshland Farm

The Quechee Inn at Marshland Farm

8/10 Good
"We really enjoyed are stay here. Staff was very friendly. The room was clean. The bed was a little soft for me but it was only one night so it was fine. We had a lovely dinner in the dining room, then the included breakfast in the morning that was satisfactory.The only issue had were the guests that checked in after us across the hall. They were very loud and at first I thought they would settle down but by 11:30 they had not. This is an old inn the walls are thin and light comes in under the doors, Which is fine but that means folks need to be respectful. I finally went out and knocked on their door. They opened it all the way up and there was 3 of them in there and one bed, weird. I told them we were trying to sleep and could they quiet down They agreed and did. We were the able to go to sleep. Other than that it was a good stay. Make sure read the interesting history of the inn. There is an article about how Julia Child visited the inn in 1997 very cool!"
Karen 1-night trip
Posted 2 hours ago
The Quechee Inn at Marshland Farm