Holiday Homes in Windsor

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Our top choices for Windsor holiday homes

Brook Road Condo

Brook Road Condo
3.0 star property
Goshen
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 AU$430
includes taxes & fees
3 Feb - 4 Feb
Brook Road Condo

Lake Front Family Friendly Escape

Lake Front Family Friendly Escape
Newport
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 AU$516
includes taxes & fees
2 Mar - 3 Mar
Lake Front Family Friendly Escape

Brook Road Condo

Brook Road Condo
Goshen
8.8 out of 10, Excellent, (14 reviews)
"Nice place close to the mountain!"
United States
Kevin N.
The price is AU$464
includes taxes & fees
3 Feb - 4 Feb
Brook Road Condo

Elysium on Little Sunapee-Dock, Firepit, Trails

Elysium on Little Sunapee-Dock, Firepit, Trails
New London
9.8 out of 10, Exceptional, (12 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 AU$1,008
includes taxes & fees
3 Feb - 4 Feb
Elysium on Little Sunapee-Dock, Firepit, Trails

Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River

Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River
Newport
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 AU$528
includes taxes & fees
3 Feb - 4 Feb
Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River

@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee

@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee
Sunapee
10.0 out of 10, Exceptional, (19 reviews)
"Great home. The hosts were accessible and responded quickly to questions. Definitely will stay there again!"
United States
Ellen V.
The price is AU$721
includes taxes & fees
25 Feb - 26 Feb
@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee

Unique Treehouse Near Mt Sunapee – No Cleaning Fee

Unique Treehouse Near Mt Sunapee – No Cleaning Fee
Newbury
10.0 out of 10, Exceptional, (27 reviews)
"Great stay. Had a wonderful time."
United States
Chris P.
The price is AU$636
includes taxes & fees
5 Feb - 6 Feb
Unique Treehouse Near Mt Sunapee – No Cleaning Fee

Chic Farmhouse Decor | Deck w/View

Chic Farmhouse Decor | Deck w/View
Sunapee
10.0 out of 10, Exceptional, (51 reviews)
"Loved our stay and will definitely return!"
United States
Jenifer S.
The price is AU$639
includes taxes & fees
1 Mar - 2 Mar
Chic Farmhouse Decor | Deck w/View

Luxury Condo Tucked in the Heart of Killington

Luxury Condo Tucked in the Heart of Killington
Killington
9.0 out of 10, Wonderful, (2 reviews)
"Comfortable stay, great location. "
United States
Marjana
The price is AU$521
includes taxes & fees
3 Feb - 4 Feb
Luxury Condo Tucked in the Heart of Killington

Charming Lakefront Cottage on Lake Mascoma

Charming Lakefront Cottage on Lake Mascoma
Enfield
10.0 out of 10, Exceptional, (20 reviews)
"Lovely location and beautiful well equipped house. "
United States
Anne S.
The price is AU$835
includes taxes & fees
3 Feb - 4 Feb
Charming Lakefront Cottage on Lake Mascoma

King Size Master With Attached Bath,Pool Table, Open Kitchen,2 Full Baths

King Size Master With Attached Bath,Pool Table, Open Kitchen,2 Full Baths
Bethel
10.0 out of 10, Exceptional, (66 reviews)
"Very cozy, warm and inviting. Beds were all comfortable. House is big enough to have your own space yet intimate enough for pool, and family game night. Highly recommend!"
United States
Christine F.
The price is AU$382
includes taxes & fees
11 Feb - 12 Feb
King Size Master With Attached Bath,Pool Table, Open Kitchen,2 Full Baths

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 AU$905
includes taxes & fees
3 Feb - 4 Feb
Large Killington Area Home | Sleeps 7 | Game Room

Breakaway House by Killington Vacation Rentals

Breakaway House by Killington Vacation Rentals
3.0 star property
Killington
The price is AU$1,158
includes taxes & fees
3 Feb - 4 Feb
Breakaway House by Killington Vacation Rentals

Charming 3-Bedroom House. Walk to Sunapee Harbor and Short Drive to Mt. Sunapee

Charming 3-Bedroom House. Walk to Sunapee Harbor and Short Drive to Mt. Sunapee
Sunapee
9.2 out of 10, Wonderful, (5 reviews)
"Great location to walk into town."
United States
Carol G.
The price is AU$1,032
includes taxes & fees
9 Feb - 10 Feb
Charming 3-Bedroom House. Walk to Sunapee Harbor and Short Drive to Mt. Sunapee

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 AU$561
includes taxes & fees
2 Mar - 3 Mar
Chester Farmhouse Ski Retreat near Slopes

Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace

Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace
Killington
The price is AU$636
includes taxes & fees
3 Feb - 4 Feb
Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace

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, (104 reviews)
"Had a wonderful stay. Clean,well kept and cozy."
United States
Edwin G.
The price is AU$671
includes taxes & fees
4 Feb - 5 Feb
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Fun In Fun Out Ski Home: Main Floor. Renovated 3BR/2BA. Hot Tub.

Fun In Fun Out Ski Home: Main Floor. Renovated 3BR/2BA. Hot Tub.
Killington
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 AU$931
includes taxes & fees
3 Feb - 4 Feb
Fun In Fun Out Ski Home: Main Floor. Renovated 3BR/2BA. Hot Tub.

180-degree panoramic views of Vermont's mountains from the living room and Deck

180-degree panoramic views of Vermont's mountains from the living room and Deck
Hartford
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 AU$719
includes taxes & fees
3 Feb - 4 Feb
180-degree panoramic views of Vermont's mountains from the living room and Deck

CozyDen-Location, Fireplace, Ski Off/Shuttle On!

CozyDen-Location, Fireplace, Ski Off/Shuttle On!
Killington
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 AU$608
includes taxes & fees
8 Feb - 9 Feb
CozyDen-Location, Fireplace, Ski Off/Shuttle On!
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

Find out more about Windsor

Windsor Holiday Homes information

Number of reviews
Accommodation
772 Holiday Homes
Lowest Price
AU$430
Highest Price
AU$2,327