A snow-covered river valley with a bridge and a town.

Holiday Homes in Windsor

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Check prices for these dates

In two weeks
14 Aug - 16 Aug
In two months
25 Sept - 27 Sept
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

Our top choices for Windsor holiday homes

Property grounds

Beautiful 3-bedroom house with AC in charming Bridgewater

Beautiful 3-bedroom house with AC in charming Bridgewater
Bridgewater
The price is €417
includes taxes & fees
29 Jul - 30 Jul
Beautiful 3-bedroom house with AC in charming Bridgewater
Smart TV, fireplace, video games, books

Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
Mt Holly
9.8 out of 10, Exceptional, (42 reviews)
The price is €434
includes taxes & fees
29 Jul - 30 Jul
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
Terrace/patio

Okemo's Back Room - in the heart of the village on the shuttle route!

Okemo's Back Room - in the heart of the village on the shuttle route!
Ludlow
9.6 out of 10, Exceptional, (16 reviews)
"Cool building, right on main street. Building is undergoing renovation on back porches so some construction material and disruption. The kitchen was not well equiped and needs an update. However, the space is really cool, very open, big bedrooms, decent bedding. Shower is a little small but nice. Good value"
United States
jonathan w.
The price is €354
includes taxes & fees
29 Jul - 30 Jul
Okemo's Back Room - in the heart of the village on the shuttle route!
Coffee/tea maker, fridge, microwave, oven

Soonipi Casa by Sunapee Stays Peekaboo views of Mount Sunapee

Soonipi Casa by Sunapee Stays Peekaboo views of Mount Sunapee
Sunapee
10.0 out of 10, Exceptional, (58 reviews)
"Wonderful place to stay for our trip. Great location and the house was nicely updated. "
United States
Andrew W.
The price is €466
includes taxes & fees
25 Aug - 26 Aug
Soonipi Casa by Sunapee Stays Peekaboo views of Mount Sunapee
TV, fireplace, table football, stereo

Bear`s Den in Ludlow, Okemo Views + Epic Game Room

Bear`s Den in Ludlow, Okemo Views + Epic Game Room
Ludlow
The price is €357
includes taxes & fees
3 Aug - 4 Aug
Bear`s Den in Ludlow, Okemo Views + Epic Game Room
Interior

CozyDen - AC, Grill, Bike to Mountain, Porch!

CozyDen - AC, Grill, Bike to Mountain, Porch!
Killington
9.4 out of 10, Exceptional, (3 reviews)
"Place was clean and location was great"
United States
Berni H.
The price is €244
includes taxes & fees
4 Aug - 5 Aug
CozyDen - AC, Grill, Bike to Mountain, Porch!
Exterior

Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!

Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!
Mount Holly
10.0 out of 10, Exceptional, (11 reviews)
"We had a great time in this beautiful house for a family ski trip. It is located right off the main highway and 8min drive away from Okemo. It has all the amenities we wanted- including hot tub, cozy underground family entertainment room and parking garage. Heidi, the host was super prompt and all instructions about the house were very thorough. "
United States
Chi L.
The price is €704
includes taxes & fees
29 Jul - 30 Jul
Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!
TV, fireplace

Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.

Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.
Bridgewater
8.8 out of 10, Excellent, (3 reviews)
"Great place for a ski weekend"
United States
Kathryn F.
Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.
Exterior

Tiffany Hill Treehouse by Sunapee Stays | Fireplace + Deck + Mount Sunapee

Tiffany Hill Treehouse by Sunapee Stays | Fireplace + Deck + Mount Sunapee
Newbury
10.0 out of 10, Exceptional, (31 reviews)
"Such a magical, detail-oriented design--it was so fun just exploring all the creative elements built into the treehouse, and everything was luxurious and comfy. We had a lovely stay!"
United States
GennaRose N.
The price is €516
includes taxes & fees
29 Jul - 30 Jul
Tiffany Hill Treehouse by Sunapee Stays | Fireplace + Deck + Mount Sunapee
Coffee/tea maker, fridge, microwave, oven

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, (113 reviews)
"Clean great cozy place!"
United States
Himanshu P.
The price is €407
includes taxes & fees
29 Jul - 30 Jul
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Exterior

Cozy Vermont Cabin · Mountain Views · Near Okemo

Cozy Vermont Cabin · Mountain Views · Near Okemo
Chester
10.0 out of 10, Exceptional, (4 reviews)
"Clean, spacous house, good location and great scenes of the mountains."
United States
pauline
The price is €902
includes taxes & fees
4 Aug - 5 Aug
Cozy Vermont Cabin · Mountain Views · Near Okemo
TV, fireplace, books

@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, (26 reviews)
"The perfect winter stay for our family! Perfect location, close to Mount Sunapee. Gorgeous views and home. Host was extremely welcoming and responsive, and the whole stay was easy."
United States
Amanda R.
The price is €480
includes taxes & fees
2 Aug - 3 Aug
@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee
Interior

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
8.4 out of 10, Very good, (5 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 €594
includes taxes & fees
4 Aug - 5 Aug
180-degree panoramic views of Vermont's mountains from the living room and Deck
Dining

Charming Chester Farmhouse near Near VT Slopes

Charming Chester Farmhouse near Near VT Slopes
Chester Depot
9.4 out of 10, Exceptional, (22 reviews)
"We had a great stay! The house was clean, comfortable, and exactly as described. The location was perfect and the host was very responsive. We’d definitely stay here again and highly recommend it."
United States
Stephanie F.
The price is €362
includes taxes & fees
30 Jul - 31 Jul
Charming Chester Farmhouse near Near VT Slopes
Dining

New Ludlow Village Home with Stunning Okemo Mountain View

New Ludlow Village Home with Stunning Okemo Mountain View
Ludlow
10.0 out of 10, Exceptional, (17 reviews)
"Second time we have stayed here. Amazing home, amazing location. The flow and design makes us happy "
United States
karyn r.
The price is €524
includes taxes & fees
10 Aug - 11 Aug
New Ludlow Village Home with Stunning Okemo Mountain View
Smart TV, video games, books

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
9.6 out of 10, Exceptional, (8 reviews)
"Great stay, the boys will be back! "
United States
Susan B.
The price is €697
includes taxes & fees
25 Aug - 26 Aug
Charming 3-Bedroom House. Walk to Sunapee Harbor and Short Drive to Mt. Sunapee
Exterior

Charming Lakefront Cottage on Lake Mascoma

Charming Lakefront Cottage on Lake Mascoma
Enfield
10.0 out of 10, Exceptional, (24 reviews)
"Couple day getaway, beautiful views right on the water plenty of windows, well stocked on house essentials"
United States
Stephanie V.
Charming Lakefront Cottage on Lake Mascoma
Property grounds

Lakefront Family Fun Retreat

Lakefront Family Fun Retreat
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 €710
includes taxes & fees
4 Aug - 5 Aug
Lakefront Family Fun Retreat
TV, fireplace, Netflix, table football

Tanglewood Vista at Killington: Great Group Ski Home Close to Mountain. Hot Tub.

Tanglewood Vista at Killington: Great Group Ski Home Close to Mountain. Hot Tub.
Killington
9.8 out of 10, Exceptional, (56 reviews)
"Perfect for a large group or a couple of families."
United States
Mark B.
The price is €646
includes taxes & fees
29 Jul - 30 Jul
Tanglewood Vista at Killington: Great Group Ski Home Close to Mountain. Hot Tub.
House, 6 Bedrooms | Living area

Breakaway House by Killington Vacation Rentals

Breakaway House by Killington Vacation Rentals
3.0 star property
Killington
The price is €639
includes taxes & fees
29 Jul - 30 Jul
Breakaway House by Killington Vacation Rentals
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

The Mountain Inn at Killington

The Mountain Inn at Killington

10/10 Excellent
"Nice quiet hotel with a beautiful view."
DAVID 1-night trip
Posted 4 hours ago
The Mountain Inn at Killington

Find out more about Windsor

Windsor Holiday Homes information

Number of reviews
319
Accommodation
854 Holiday Homes
Lowest Price
€244
Highest Price
€902