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

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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Windsor holiday homes

A wooden deck with a white railing overlooking a lake, surrounded by trees and a small house.

1. Lakefront Family Fun Retreat

Lakefront Family Fun Retreat
Newport
10.0 out of 10, Exceptional, (5 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 £308
includes taxes & fees
28 Sept - 29 Sept
Lakefront Family Fun Retreat
A spacious living room with a fireplace, large windows, and a cozy seating area.

2. @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 £422
includes taxes & fees
29 Sept - 30 Sept
@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee
A large house with a fire pit and outdoor seating.

3. Beautiful 3-bedroom house with AC in charming Bridgewater

Beautiful 3-bedroom house with AC in charming Bridgewater
Bridgewater
10.0 out of 10, Exceptional, (2 reviews)
"Great house with fun decorations. Comfortable with lots of room; full kitchen with ample dining area. Loved the coffee available and the sound machine in the bedroom- great conveniences! Communication around booking were great with easy check in and check out."
United States
Susan S.
The price is £388
includes taxes & fees
16 Sept - 17 Sept
Beautiful 3-bedroom house with AC in charming Bridgewater
A room with a large sliding glass door leading to a balcony with a wooden deck and a scenic view of the countryside.

4. 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
9.0 out of 10, Wonderful, (7 reviews)
"Plenty of room beautiful view"
United States
Anthony A.
The price is £392
includes taxes & fees
16 Sept - 17 Sept
180-degree panoramic views of Vermont's mountains from the living room and Deck
A modern kitchen with white cabinets, stainless steel appliances, a granite countertop, and a hanging light fixture.

5. 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 £305
includes taxes & fees
16 Sept - 17 Sept
Soonipi Casa by Sunapee Stays Peekaboo views of Mount Sunapee
A cozy cabin interior with a stone fireplace, leather sofas, and large windows offering a view of the forest.

6. 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 £365
includes taxes & fees
22 Sept - 23 Sept
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
A modern kitchen with a central island, built-in appliances, and a dining area with a wooden table and chairs.

7. 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, (18 reviews)
"This was a lovely, well-kept home in a great location to Okemo Mountain."
United States
Nancy F.
The price is £441
includes taxes & fees
17 Sept - 18 Sept
New Ludlow Village Home with Stunning Okemo Mountain View
A two-story house with a deck, surrounded by dense forest.

8. 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, (4 reviews)
"Clean, spacous house, good location and great scenes of the mountains."
United States
pauline
The price is £722
includes taxes & fees
28 Sept - 29 Sept
4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo
A wooden cabin with multiple windows and a balcony, surrounded by trees.

9. 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, (32 reviews)
"The Treehouse provided an excellent retreat. Beautiful property and excellent hosts. "
United States
T G.
The price is £337
includes taxes & fees
16 Sept - 17 Sept
Tiffany Hill Treehouse by Sunapee Stays | Fireplace + Deck + Mount Sunapee
A two-story house with a covered porch and a garage.

10. 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 £631
includes taxes & fees
16 Sept - 17 Sept
Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!
A cozy living room with a fireplace, comfortable seating, and a television.

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

Bear`s Den in Ludlow, Okemo Views + Epic Game Room
Ludlow
The price is £294
includes taxes & fees
20 Sept - 21 Sept
Bear`s Den in Ludlow, Okemo Views + Epic Game Room
A spacious living room with a grey sofa, ottoman, and a coffee table. There are wooden beams, a bookshelf, and a dining area with a table and chairs.

12. 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, (10 reviews)
"Great stay, the boys will be back! "
United States
Susan B.
The price is £498
includes taxes & fees
29 Sept - 30 Sept
Charming 3-Bedroom House. Walk to Sunapee Harbor and Short Drive to Mt. 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.

13. CozyDen - AC, Bike to Mountain, Porch!

CozyDen - AC, 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 £205
includes taxes & fees
16 Sept - 17 Sept
CozyDen - AC, Bike to Mountain, Porch!
A kitchen with white cabinetry, a stainless steel refrigerator, a coffee maker, and a dining area with two chairs.

14. Luxury Condo Tucked in the Heart of Killington

Luxury Condo Tucked in the Heart of Killington
Killington
The price is £212
includes taxes & fees
29 Sept - 30 Sept
Luxury Condo Tucked in the Heart of Killington

15. Charming Chester Farmhouse near Near VT Slopes

Charming Chester Farmhouse near Near VT Slopes
Chester Depot
9.4 out of 10, Exceptional, (22 reviews)
"Beautiful classic farmhouse in lovely neighbourhood."
United States
Kimberly B.
The price is £313
includes taxes & fees
28 Sept - 29 Sept
Charming Chester Farmhouse near Near VT Slopes
A cozy living room with a large window overlooking a lake, a wooden ceiling, and a guitar on the wall.

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

Elysium on Little Sunapee-Dock, Firepit, Trails
New London
9.8 out of 10, Exceptional, (16 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 £676
includes taxes & fees
21 Sept - 22 Sept
Elysium on Little Sunapee-Dock, Firepit, Trails
A deck with outdoor furniture, a table, and a view of a forested hillside.

17. Modern Farm House…minutes to Okemo; 2 King beds!

Modern Farm House…minutes to Okemo; 2 King beds!
Mount Holly
9.6 out of 10, Exceptional, (20 reviews)
"Fantastic house! Christine was easy to communicate with and made us and our dogs feel incredibly welcome. Looking forward to staying there again."
United States
Rachel L.
The price is £502
includes taxes & fees
17 Sept - 18 Sept
Modern Farm House…minutes to Okemo; 2 King beds!
A person relaxing in a hot tub outdoors with string lights in a forested area.

18. Secluded Spa Retreat | Hot Tub + Sauna | Okemo

Secluded Spa Retreat | Hot Tub + Sauna | Okemo
Ludlow
The price is £332
includes taxes & fees
17 Sept - 18 Sept
Secluded Spa Retreat | Hot Tub + Sauna | Okemo
A cabin with a deck and a stone chimney.

19. The Navillus House: Hot Tub, Ski On/Ski Off, A/C. Discounted Ski Rentals.

The Navillus House: Hot Tub, Ski On/Ski Off, A/C. Discounted Ski Rentals.
Killington
10.0 out of 10, Exceptional, (63 reviews)
"Great stay, everything was clean and location was amazing."
United States
John D.
The price is £796
includes taxes & fees
16 Sept - 17 Sept
The Navillus House: Hot Tub, Ski On/Ski Off, A/C. Discounted Ski Rentals.
A modern living room with a dark gray sectional sofa, a white armchair, a wooden coffee table, and a spiral staircase.

20. Slopeside Estate Guesthouse: Hot tub, AC, Grill

Slopeside Estate Guesthouse: Hot tub, AC, Grill
Killington
The price is £703
includes taxes & fees
17 Sept - 18 Sept
Slopeside Estate Guesthouse: Hot tub, AC, Grill
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
"Very nice location, friendly staff, parking onsite."
Jadwiga 7-night trip
Posted 10 hours ago
The Mountain Inn at Killington

Find out more about Windsor

Windsor Holiday Homes information

Number of reviews
7,289
Accommodation
810 Holiday Homes
Lowest Price
£85
Highest Price
£193