Windsor County Holiday Rentals

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Our top choices for Windsor County holiday rentals

Treehouse at Wise Pines- NoBo

Treehouse at Wise Pines- NoBo
Woodstock
9.6 out of 10, Exceptional, (15 reviews)
"Cleanness, quiet, and friendly "
United States
Zhongchun
The price is HK$1,176
HK$1,475 total
includes taxes & fees
6 Apr - 7 Apr
Treehouse at Wise Pines- NoBo

Addie's Place: A Quiet and Quirky Guesthouse

Addie's Place: A Quiet and Quirky Guesthouse
Hartford
10.0 out of 10, Exceptional, (9 reviews)
"Perfect size and location! "
United States
Lyn H.
The price is HK$724
HK$1,447 total
includes taxes & fees
6 Apr - 7 Apr
Addie's Place: A Quiet and Quirky Guesthouse

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, (8 reviews)
"The accommodations were very lovely. The host was friendly."
United States
Serge
The price is HK$1,043
HK$2,326 total
includes taxes & fees
6 Apr - 7 Apr
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

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, (17 reviews)
"It was an amazing experience! "
United States
Gruha
The price is HK$1,235
HK$2,269 total
includes taxes & fees
6 Apr - 7 Apr
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

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, (78 reviews)
"Unit was as advertised. Clean and comfortable."
United States
Ralph D.
The price is HK$588
HK$2,025 total
includes taxes & fees
8 Apr - 9 Apr
Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Ludlow
9.8 out of 10, Exceptional, (108 reviews)
"We enjoyed our stay, the house was lovely and close to everything in Ludlow and Okemo."
United States
Hannah M.
The price is HK$882
HK$2,377 total
includes taxes & fees
6 Apr - 7 Apr
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

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

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Ludlow
7.6 out of 10, Good, (56 reviews)
"The place was very dirty. The linens were dirty, the pots/pans and all of the cooking utensils were dirty. There was a rubber band on the floor in bathroom that didn't belong to us.There was only 3 forks and a few spoons. Very little silverwear."
United States
Leigh-Ellen F.
The price is HK$415
HK$2,300 total
includes taxes & fees
6 Apr - 7 Apr
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

Vermont Suite | 10 Min to Woodstock & Killington

Vermont Suite | 10 Min to Woodstock & Killington
Bridgewater
10.0 out of 10, Exceptional, (5 reviews)
"We had a lovely time in Woodstock Vermont. The Bridgewater Inn was cozy and perfect for our weekend get away"
United States
Rosie L.
The price is HK$619
HK$1,509 total
includes taxes & fees
6 Apr - 7 Apr
Vermont Suite | 10 Min to Woodstock & Killington

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)
"Perfect spot to jump onto the mountain and ski. Two adults and 4 kids, and we had plenty of space for a long weekend."
United States
Allison T.
The price is HK$980
HK$3,268 total
includes taxes & fees
7 Apr - 8 Apr
Ski-In/Out Condo with Mountain Views, and Washer/Dryer

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)
"Great property, clean and close to the slope"
United States
tiliger01
The price is HK$400
HK$1,757 total
includes taxes & fees
8 Apr - 9 Apr
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

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$745
HK$1,910 total
includes taxes & fees
8 Apr - 9 Apr
2nd-floor downtown Ludlow studio condo with kitchenette, streaming

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, (107 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$1,058
HK$2,233 total
includes taxes & fees
3 May - 4 May
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

Cozy Private Cabin in Andover - Fireplace & Hot tub

Cozy Private Cabin in Andover - Fireplace & Hot tub
Andover
The price is HK$1,716
HK$3,906 total
includes taxes & fees
6 Apr - 7 Apr
Cozy Private Cabin in Andover - Fireplace & Hot tub

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Ludlow
9.8 out of 10, Exceptional, (85 reviews)
"We had a great stay at this home for a long weekend skiing at Okemo. "
United States
Lisa W.
The price is HK$882
HK$2,377 total
includes taxes & fees
6 Apr - 7 Apr
Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route

Ski Haven: 1-Bed Ski-in/out Condo, Okemo Base Area

Ski Haven: 1-Bed Ski-in/out Condo, Okemo Base Area
Clock Tower Base Area
10.0 out of 10, Exceptional, (13 reviews)
"Great communication, ski in/out location"
United States
Robin
The price is HK$1,168
HK$3,286 total
includes taxes & fees
6 Apr - 7 Apr
Ski Haven: 1-Bed Ski-in/out Condo, Okemo Base Area

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$1,681
HK$3,866 total
includes taxes & fees
8 Apr - 9 Apr
Gnome Home Mountain Ski Chalet w/Sauna Killington

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, (25 reviews)
"Great rate for a place with all the basics!"
United States
Macgregor
The price is HK$784
HK$1,976 total
includes taxes & fees
7 Apr - 8 Apr
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street

Charming Chester Farmhouse near Near VT Slopes

Charming Chester Farmhouse near Near VT 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$1,552
HK$3,222 total
includes taxes & fees
6 Apr - 7 Apr
Charming Chester Farmhouse near Near VT Slopes

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$980
HK$2,387 total
includes taxes & fees
7 Apr - 8 Apr
Condo in the heart of town near skiing - less than a mile to Okemo Mountain

Ground Floor ski-in/out condo, full kitchen & high-speed WiFi

Ground Floor ski-in/out condo, full kitchen & high-speed WiFi
Clock Tower Base Area
9.4 out of 10, Exceptional, (27 reviews)
"Clean room and very comfortable bed. Was ready for check in sooner than expected. "
United States
Wilson V.
The price is HK$1,176
HK$3,020 total
includes taxes & fees
7 Apr - 8 Apr
Ground Floor ski-in/out condo, full kitchen & high-speed WiFi
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