Windsor County Holiday Rentals

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Our top choices for Windsor County holiday 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, (4 reviews)
"Perfect size and location! "
United States
Lyn H.
The price is HK$749
HK$1,471 total
includes taxes & fees
24 Jan - 25 Jan
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 HK$1,170
HK$1,467 total
includes taxes & fees
26 Jan - 27 Jan
Treehouse at Wise Pines- SoBo
Property grounds

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$803
HK$1,740 total
includes taxes & fees
26 Jan - 27 Jan
Vermont Suite | 10 Min to Woodstock & 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 HK$1,467
HK$2,542 total
includes taxes & fees
26 Jan - 27 Jan
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
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, (6 reviews)
"Cabin was spotless and exactly what I expected"
United States
mark g.
The price is HK$1,325
HK$2,663 total
includes taxes & fees
17 Feb - 18 Feb
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Outdoor dining

Ski-in/out mountainside condo with balcony, washer/dryer & high-speed WiFi

Ski-in/out mountainside condo with balcony, washer/dryer & high-speed WiFi
Clock Tower Base Area
8.6 out of 10, Excellent, (14 reviews)
"Excellent Location.. "
United States
Juan Carlos L.
The price is HK$834
HK$2,556 total
includes taxes & fees
26 Jan - 27 Jan
Ski-in/out mountainside condo with balcony, washer/dryer & high-speed WiFi
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 HK$865
HK$2,223 total
includes taxes & fees
26 Jan - 27 Jan
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
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
2.0 star property
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$2,339
HK$5,493 total
includes taxes & fees
9 Feb - 10 Feb
Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington
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 HK$943
HK$2,784 total
includes taxes & fees
26 Jan - 27 Jan
Well-appointed studio right downtown - less than a mile to Okemo Mountain
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 HK$936
HK$2,090 total
includes taxes & fees
26 Jan - 27 Jan
Efficient condo near slopes with kitchenette & great location
Living area

Cozy Private Cabin in Andover - Fireplace & Hot tub

Cozy Private Cabin in Andover - Fireplace & Hot tub
2.0 star property
Andover
The price is HK$1,569
HK$3,661 total
includes taxes & fees
27 Jan - 28 Jan
Cozy Private Cabin in Andover - Fireplace & Hot tub
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 HK$1,014
HK$2,432 total
includes taxes & fees
26 Jan - 27 Jan
2nd-floor downtown Ludlow studio condo with kitchenette, streaming
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 HK$1,068
HK$2,708 total
includes taxes & fees
26 Jan - 27 Jan
Condo in the heart of town near skiing - less than a mile to Okemo Mountain
Interior

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$655
HK$2,887 total
includes taxes & fees
3 Feb - 4 Feb
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
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 HK$2,247
HK$4,585 total
includes taxes & fees
2 Feb - 3 Feb
Gnome Home Mountain Ski Chalet w/Sauna Killington
Property grounds

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, (75 reviews)
"Perfect location for a quick ski trip. "
United States
Michael D.
The price is HK$1,084
HK$2,925 total
includes taxes & fees
27 Jan - 28 Jan
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Dining

Chester Farmhouse Ski Retreat near Slopes

Chester Farmhouse Ski Retreat near Slopes
Chester Depot
9.6 out of 10, Exceptional, (18 reviews)
"This was my second time staying at this property. Everything was great just like last year. I highly recommend it if you are staying in Chester, VT. "
United States
Lori N.
The price is HK$1,240
HK$2,821 total
includes taxes & fees
29 Jan - 30 Jan
Chester Farmhouse Ski Retreat near Slopes
Interior

RoundTop Chalet | Hot Tub, Fire Pit & Mountain Views near Killington & Okemo

RoundTop Chalet | Hot Tub, Fire Pit & Mountain Views near Killington & Okemo
2.0 star property
Plymouth
The price is HK$1,641
HK$4,803 total
includes taxes & fees
27 Jan - 28 Jan
RoundTop Chalet | Hot Tub, Fire Pit & Mountain Views near Killington & Okemo
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 HK$1,754
HK$3,128 total
includes taxes & fees
4 Feb - 5 Feb
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
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, (172 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 HK$2,339
HK$3,674 total
includes taxes & fees
18 Feb - 19 Feb
Okemo Mt. Family Affordable 1st floor, village shuttle, walk to town, Dogs OK
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

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

10/10 Excellent
"Good rooms"
ke 3-night trip
Posted 2 days ago
Holiday Inn Club Vacations Mount Ascutney Resort by IHG