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
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Windsor holiday homes

A golf course with sand bunkers and a forested area.

1. Peaceful Stay w/ Pond & Massage Chair | Near Okemo

Peaceful Stay w/ Pond & Massage Chair | Near Okemo
Ludlow
The price is NZ$755
includes taxes & fees
27 Oct - 28 Oct
Peaceful Stay w/ Pond & Massage Chair | Near Okemo
A large house with a fire pit and outdoor seating.

2. Pet Friendly | Game Room | Minutes to Woodstock and Killington

Pet Friendly | Game Room | Minutes to Woodstock and Killington
Bridgewater
10.0 out of 10, Exceptional, (4 reviews)
"We loved the farmhouse. It was very charming and cozy. Plenty of space for us and exactly as advertised. We would definitely stay here again. Thank you"
United States
Lisa G.
The price is NZ$900
includes taxes & fees
27 Oct - 28 Oct
Pet Friendly | Game Room | Minutes to Woodstock and Killington
A red house with a gravel driveway and lush greenery.

3. The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6

The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6
Plymouth
The price is NZ$990
includes taxes & fees
27 Oct - 28 Oct
The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6
A two-story house with a deck, surrounded by dense forest.

4. 4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo

4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo
Chester
10.0 out of 10, Exceptional, (6 reviews)
"Clean, spacous house, good location and great scenes of the mountains."
United States
pauline
The price is NZ$1,722
includes taxes & fees
27 Oct - 28 Oct
4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo
A wooden deck with a white railing overlooking a lake, surrounded by trees and a small house.

5. Lakefront Family Fun Retreat

Lakefront Family Fun Retreat
Newport
10.0 out of 10, Exceptional, (5 reviews)
"Had a lot here to use and The place was very cute. It’s good if you have small kids they have a lot for that sort of thing. Very clean as well"
United States
sean c.
The price is NZ$706
includes taxes & fees
1 Nov - 2 Nov
Lakefront Family Fun Retreat
A spacious living room with a fireplace, large windows, and a cozy seating area.

6. @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, (27 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 NZ$991
includes taxes & fees
5 Nov - 6 Nov
@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee
A yellow building with a porch and a sign that reads "Brook Road Inn."

7. Brook Road Condo

Brook Road Condo
Goshen
8.8 out of 10, Excellent, (15 reviews)
"Nice place for a mountain stay"
United States
Meghan B.
The price is NZ$565
includes taxes & fees
27 Oct - 28 Oct
Brook Road Condo
A cozy living room with a fireplace, comfortable seating, and a television.

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

Bear`s Den in Ludlow, Okemo Views + Epic Game Room
Ludlow
The price is NZ$728
includes taxes & fees
3 Nov - 4 Nov
Bear`s Den in Ludlow, Okemo Views + Epic Game Room
A window with a view of a lake at sunset, trees, and a distant shoreline.

9. The Shaker Cottage on Lake Mascoma

The Shaker Cottage on Lake Mascoma
Enfield
The price is NZ$730
includes taxes & fees
27 Oct - 28 Oct
The Shaker Cottage on Lake Mascoma
A cozy living room with a brick fireplace, comfortable seating, and large windows offering a view of the outdoors.

10. 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.
The price is NZ$1,202
includes taxes & fees
27 Oct - 28 Oct
Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.
A kitchen with white cabinetry, a stainless steel refrigerator, a coffee maker, and a dining area with two chairs.

11. Luxury Condo Tucked in the Heart of Killington

Luxury Condo Tucked in the Heart of Killington
Killington
10.0 out of 10, Exceptional, (1 review)
"We were very surprised. The accommodation's well worth the amount we paid. I was surprised how from the start to the close of our Anniversary get away It was such an easygoing experience. The host left fresh towels and bedding linens. The host kept in contact the entire way booking this condo. It was roomy nice Quiet!! I loved the privacy yet close to everything Killington has to offer. Our anniversary was special as we went with the host recommendation for a local resturaunt the Garlic. We have...
United States
Melinda D.
The price is NZ$471
includes taxes & fees
3 Nov - 4 Nov
Luxury Condo Tucked in the Heart of Killington
A cozy living room with a sofa, a dining table with chairs, a small side table, and a wooden floor.

12. 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 NZ$504
includes taxes & fees
26 Nov - 27 Nov
Brook Road Condo
A spacious living room with a large sectional sofa, a wooden coffee table, and a fireplace. A staircase leads to an upper level with a balcony.

13. Powder House on East Mountain | Summer Retreat

Powder House on East Mountain | Summer Retreat
Killington
10.0 out of 10, Exceptional, (2 reviews)
"Cool place ! Close to the mountain and access road. "
United States
David F.
The price is NZ$290
includes taxes & fees
31 Oct - 1 Nov
Powder House on East Mountain | Summer Retreat
Property grounds

14. Formerly the 1806 Inn

Formerly the 1806 Inn
Newbury
The price is NZ$312
includes taxes & fees
27 Oct - 28 Oct
Formerly the 1806 Inn
A modern kitchen with white cabinets, stainless steel appliances, a granite countertop, and a hanging light fixture.

15. 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, (59 reviews)
"Wonderful place to stay for our trip. Great location and the house was nicely updated. "
United States
Andrew W.
The price is NZ$758
includes taxes & fees
1 Nov - 2 Nov
Soonipi Casa by Sunapee Stays Peekaboo views of Mount Sunapee
A modern living room with a flat-screen TV, grey sofas, a dining table with chairs, and a large window with a view of greenery.

16. CozyDen- Location, Ski Off/ Shuttle On

CozyDen- Location, Ski Off/ Shuttle On
Killington
9.6 out of 10, Exceptional, (4 reviews)
"Place was clean and location was great"
United States
Berni H.
The price is NZ$491
includes taxes & fees
27 Oct - 28 Oct
CozyDen- Location, Ski Off/ Shuttle On
A cozy cabin interior with a stone fireplace, leather sofas, and large windows offering a view of the forest.

17. 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)
"This house has great hang out space and plenty of space for a big family!"
United States
Cheri V.
The price is NZ$837
includes taxes & fees
27 Oct - 28 Oct
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

18. 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, (114 reviews)
"Wendi was very responsive when I had questions. We enjoyed our weekend getaway. Great location we walked into town to the Farmers Market Sunday."
United States
Tina l.
The price is NZ$850
includes taxes & fees
18 Nov - 19 Nov
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
A modern kitchen with a central island, built-in appliances, and a dining area with a wooden table and chairs.

19. 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, (22 reviews)
"The perfect stop on the way to UVM. Super clean! Walkable eateries & a beautiful view. Thank you!"
United States
Tara
The price is NZ$1,023
includes taxes & fees
3 Nov - 4 Nov
New Ludlow Village Home with Stunning Okemo Mountain View
A cozy living room with a large window overlooking a lake, a wooden ceiling, and a guitar on the wall.

20. Elysium on Little Sunapee-Dock, Firepit, Trails

Elysium on Little Sunapee-Dock, Firepit, Trails
New London
9.8 out of 10, Exceptional, (20 reviews)
"We had a wonderful time at the lake. The house was perfect for our family as we were all able to gather together and then retreat to our own sleeping spaces. The check in process was easy and communication was great. We also got a chance to try paddle boarding! Will definitely be returning."
United States
Julie C.
The price is NZ$1,342
includes taxes & fees
27 Oct - 28 Oct
Elysium on Little Sunapee-Dock, Firepit, Trails
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

Courtyard by Marriott Hanover Lebanon

Courtyard by Marriott Hanover Lebanon

10/10 Excellent
"Excellent"
Mylene 3-night trip
Posted 14 hours ago
Courtyard by Marriott Hanover Lebanon

Find out more about Windsor

Windsor Holiday Homes information

Number of reviews
208
Accommodation
810 Holiday Homes
Lowest Price
NZ$290
Highest Price
NZ$1,722