Windsor County Holiday Rentals

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Our top choices for Windsor County holiday rentals

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 HK$844
HK$1,599 total
includes taxes & fees
22 Feb - 23 Feb
Addie's Place: A Quiet and Quirky Private Guesthouse

Vermont Suite | 10 Min to Killington & Woodstock

Vermont Suite | 10 Min to Killington & Woodstock
Bridgewater
9.2 out of 10, Wonderful, (7 reviews)
"Overall, a great stay. "
United States
Meghan J.
The price is HK$743
HK$1,667 total
includes taxes & fees
11 Mar - 12 Mar
Vermont Suite | 10 Min to Killington & Woodstock

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.
The price is HK$1,094
HK$2,381 total
includes taxes & fees
5 Mar - 6 Mar
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

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 HK$977
HK$2,247 total
includes taxes & fees
8 Mar - 9 Mar
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street

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
9.0 out of 10, Wonderful, (77 reviews)
"Perfect location for a quick ski trip. "
United States
Michael D.
The price is HK$993
HK$2,599 total
includes taxes & fees
11 Mar - 12 Mar
Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Luxury Cabin #1 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

Luxury Cabin #1 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Cavendish
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful property, quiet and peaceful location. Enjoyed the access to the hot tub, and loved having a private fire pit."
United States
David V.
The price is HK$1,899
HK$3,099 total
includes taxes & fees
9 Mar - 10 Mar
Luxury Cabin #1 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

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 HK$1,079
HK$2,142 total
includes taxes & fees
16 Mar - 17 Mar
Efficient condo near slopes with kitchenette & great location

Cozy Studio Condo with Great Location, WiFi & Kitchenette

Cozy Studio Condo with Great Location, WiFi & Kitchenette
Ludlow
8.8 out of 10, Excellent, (29 reviews)
"Great location and great place!"
United States
Linda G.
The price is HK$1,079
HK$2,190 total
includes taxes & fees
16 Mar - 17 Mar
Cozy Studio Condo with Great Location, WiFi & Kitchenette

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, (28 reviews)
"Overall very clean and nice. Needs some updating like more spoons, only 2, bigger coffee cups. And a new coffee table that is very worn. "
United States
David A.
The price is HK$1,063
HK$2,694 total
includes taxes & fees
10 Mar - 11 Mar
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

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 HK$2,227
HK$4,577 total
includes taxes & fees
10 Mar - 11 Mar
Gnome Home Mountain Ski Chalet w/Sauna Killington

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 HK$1,180
HK$2,586 total
includes taxes & fees
2 Mar - 3 Mar
Condo in the heart of town near skiing - less than a mile to Okemo Mountain

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$1,087
HK$2,399 total
includes taxes & fees
24 Feb - 25 Feb
2nd-floor downtown Ludlow studio condo with kitchenette, streaming

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

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Ludlow
7.4 out of 10, Good, (55 reviews)
"Irish Bar nearby was a plus on St. Patrick’s Day !"
United States
Warren
The price is HK$813
HK$2,811 total
includes taxes & fees
25 Feb - 26 Feb
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

Cozy Private Cabin in Andover - Fireplace & Hot tub

Cozy Private Cabin in Andover - Fireplace & Hot tub
Andover
The price is HK$1,711
HK$3,930 total
includes taxes & fees
9 Mar - 10 Mar
Cozy Private Cabin in Andover - Fireplace & Hot tub

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 HK$2,462
HK$5,594 total
includes taxes & fees
24 Feb - 25 Feb
Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington

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 HK$1,712
HK$3,423 total
includes taxes & fees
1 Mar - 2 Mar
Chester Farmhouse Ski Retreat near Slopes

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, (103 reviews)
"Great Condo. We had plenty of space. Wendi was very responsive and even accommodated us checking in an hour early when we arrived in town. We would definitely come back. "
United States
Barbara M.
The price is HK$1,610
HK$2,933 total
includes taxes & fees
9 Mar - 10 Mar
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

Ski Home/Arcade Mountain Views Near Killington/Woodstock

Ski Home/Arcade Mountain Views Near Killington/Woodstock
Stockbridge
10.0 out of 10, Exceptional, (2 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$2,682
HK$6,683 total
includes taxes & fees
9 Mar - 10 Mar
Ski Home/Arcade Mountain Views Near Killington/Woodstock

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, (174 reviews)
"Great spot to stay in with a group for skiing. Easy check in and check out process."
United States
Aidan O.
Okemo Mt. Family Affordable 1st floor, village shuttle, walk to town, Dogs OK

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 HK$2,017
HK$4,990 total
includes taxes & fees
4 Mar - 5 Mar
Large Killington Area Home | Sleeps 7 | Game Room
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