Holiday Homes in Windsor

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Check prices for these dates

In two weeks
30 Jan - 1 Feb
In two months
13 Mar - 15 Mar
In three months
10 Apr - 12 Apr
In four months
8 May - 10 May

Our top choices for Windsor holiday homes

Comfort Townhome | In-room dining

Holiday Home in Goshen

Brook Road Condo
3.0 star property
8.8 out of 10, Excellent, (3 reviews)
"Convenient location, quiet and rural. Accommodations were clean and neat. Nice to have full kitchen for meal prep and snacks."
United States
Margaret
The price is €257
includes taxes & fees
27 Jan - 28 Jan
Brook Road Condo
Exterior detail

Holiday Home in Goshen

Brook Road Condo
8.8 out of 10, Excellent, (14 reviews)
"Nice place close to the mountain!"
United States
Kevin N.
The price is €275
includes taxes & fees
29 Jan - 30 Jan
Brook Road Condo
TV, fireplace, books

Holiday Home in Sunapee

@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee
2.0 star property
10.0 out of 10, Exceptional, (18 reviews)
"Great home. The hosts were accessible and responded quickly to questions. Definitely will stay there again!"
United States
Ellen V.
The price is €398
includes taxes & fees
26 Jan - 27 Jan
@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee
Property grounds

Holiday Home in Newport

Lake Front Family Friendly Escape
10.0 out of 10, Exceptional, (4 reviews)
"Great visit! The house is perfectly outfitted for a relaxing vacation. Super clean and updated. Really enjoyed the warm waters of Crescent Lake!"
United States
Ann R.
The price is €296
includes taxes & fees
25 Jan - 26 Jan
Lake Front Family Friendly Escape
Exterior

Holiday Home in Newport

Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River
9.8 out of 10, Exceptional, (19 reviews)
"The tree house was just as pictured, beautiful inside and we had great views of the River. It was a great trip and we look forward to coming back!"
United States
Kimberly R.
The price is €325
includes taxes & fees
22 Jan - 23 Jan
Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River
TV, fireplace, computer monitors

Holiday Home in New London

Elysium on Little Sunapee-Dock, Firepit, Trails
9.8 out of 10, Exceptional, (11 reviews)
"Great Lake house with all the amenities you need for a great week!! Kitchen is well stocked. Wonderful hosts!"
United States
Caren H.
The price is €607
includes taxes & fees
27 Jan - 28 Jan
Elysium on Little Sunapee-Dock, Firepit, Trails
Interior

Holiday Home in Killington

CozyDen-Location, Fireplace, Ski Off/Shuttle On!
10.0 out of 10, Exceptional, (1 review)
"Very quiet and private feeling even though it is in a condo like setting. Very clean, and had all the conveniences we needed (A/C, coffee maker, full kitchen appliances). And so kind and personal to leave some souvenirs of the area. We felt very comfortable when every we finished our day of sightseeing to come back to our home away from home. "
United States
denise k.
The price is €303
includes taxes & fees
19 Jan - 20 Jan
CozyDen-Location, Fireplace, Ski Off/Shuttle On!
Dining

Holiday Home in Chester Depot

Chester Farmhouse Ski Retreat near Slopes
9.6 out of 10, Exceptional, (17 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 €318
includes taxes & fees
19 Jan - 20 Jan
Chester Farmhouse Ski Retreat near Slopes
Exterior

Holiday Home in Newbury

Unique Treehouse Near Mt Sunapee – No Cleaning Fee
10.0 out of 10, Exceptional, (26 reviews)
"Great stay. Had a wonderful time."
United States
Chris P.
The price is €393
includes taxes & fees
19 Jan - 20 Jan
Unique Treehouse Near Mt Sunapee – No Cleaning Fee
TV, fireplace, DVD player, offices

Holiday Home in Quechee

Spa, Fireplace & Pet Friendly - Top of the Hill
9.8 out of 10, Exceptional, (6 reviews)
"Appreciated the large outdoor deck area, grill, and plenty of space for the family to relax."
United States
Maryanne C.
The price is €516
includes taxes & fees
29 Jan - 30 Jan
Spa, Fireplace & Pet Friendly - Top of the Hill
Fridge, microwave, oven, stovetop

Holiday Home in Sunapee

Chic Farmhouse Decor | Deck w/View
10.0 out of 10, Exceptional, (51 reviews)
"This place is pristine and very cozy. Bed's are insanely comfortable too. Will definitely try to stay there again. "
United States
Peter S.
The price is €388
includes taxes & fees
28 Jan - 29 Jan
Chic Farmhouse Decor | Deck w/View
Fridge, microwave, oven, stovetop

Holiday Home in Killington

Luxury Condo Tucked in the Heart of Killington
8.0 out of 10, Very good, (1 review)
"The condo was in a beautiful location but was rather isolated from grocery and dining options. Our host was good at communicating however we received a message about the fireplace not being available to us a day before we came and we got there in the dark with no lights on. The condo itself could not really be called "luxury" as it was dated and lacked some basics like soap in the bathroom, a towel hook in the 1/2 bath, kleenex, cracked dishes, etc. Liked that it was near a waterfall and hiking...
United States
Dean
The price is €323
includes taxes & fees
27 Jan - 28 Jan
Luxury Condo Tucked in the Heart of Killington
3 bedrooms, desk, iron/ironing board, travel cot

Holiday Home in Bridgewater

Blueberry Hill Escape | Pet Friendly | HotTub | AC
9.6 out of 10, Exceptional, (17 reviews)
"Very nice home! Plenty of room for everyone and a short drive to the mountain! Perfect "
United States
Gerri B.
The price is €491
includes taxes & fees
21 Jan - 22 Jan
Blueberry Hill Escape | Pet Friendly | HotTub | AC
Property grounds

Holiday Home in Killington

Fun In Fun Out Ski Home: Main Floor. Renovated 3BR/2BA. Hot Tub.
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"Such an awesome place! The booking/check-in process was seamless and the location cannot be beat! Will definitely be booking again. "
United States
Catherine S.
The price is €589
includes taxes & fees
19 Jan - 20 Jan
Fun In Fun Out Ski Home: Main Floor. Renovated 3BR/2BA. Hot Tub.
Fridge, microwave, oven, stovetop

Holiday Home in Ludlow

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
9.8 out of 10, Exceptional, (104 reviews)
"Had a wonderful stay. Clean,well kept and cozy."
United States
Edwin G.
The price is €372
includes taxes & fees
20 Jan - 21 Jan
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Smart TV, fireplace, video games, books

Holiday Home in Mt Holly

Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
9.8 out of 10, Exceptional, (36 reviews)
"Wonderful cabin, well stocked, host was attentive and quick to address any questions."
United States
Eyal O.
The price is €549
includes taxes & fees
20 Jan - 21 Jan
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
Interior

Holiday Home in Hartford

180-degree panoramic views of Vermont's mountains from the living room and Deck
8.0 out of 10, Very good, (2 reviews)
"The house was absolutely beautiful. A unique mix of modern and 70’s. The layout was spot on . We were only there one night , a very quick stop over but it was so comfortable and cozy. The host was so easy to communicate with and was very accommodating. Plenty of room to sleep a large group and the views….you have to see in person. Stunning . I travel a lot and use VRBO for all of my travels. This was one of the best experiences I have had . I recommend 100%. "
United States
Mary Anne C.
The price is €432
includes taxes & fees
20 Jan - 21 Jan
180-degree panoramic views of Vermont's mountains from the living room and Deck
Interior

Holiday Home in Killington

Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace
2.0 star property
The price is €520
includes taxes & fees
19 Jan - 20 Jan
Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace
Smart TV, fireplace

Holiday Home in The Woods

Bearmont- Pool, HotTub, Fireplace
10.0 out of 10, Exceptional, (7 reviews)
"Great location and a great place. Felt right at home"
United States
Tyler B.
Bearmont- Pool, HotTub, Fireplace
Smart TV, fireplace

Holiday Home in Killington

Alpine Chalet, Fireplace, Pool, Gym, At Pico.
2.0 star property
10.0 out of 10, Exceptional, (5 reviews)
"Such a great spot."
United States
Kathleen G.
Alpine Chalet, Fireplace, Pool, Gym, At Pico.
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 Hotel Reviews

Align Inn Vermont

Align Inn Vermont

10/10 Excellent
"Clean, quiet, good breakfast. Check in was easy and staff was friendly. "
Christopher 1-night trip
Posted 2 days ago
Align Inn Vermont

Find out more about Windsor

Windsor Holiday Homes information

Number of reviews
293
Accommodation
772 Holiday Homes
Lowest Price
€257
Highest Price
€607