Holiday Homes in Windsor

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Check prices for these dates

In two weeks
8 May - 10 May
In two months
19 Jun - 21 Jun
In three months
17 Jul - 19 Jul
In four months
14 Aug - 16 Aug

Our top choices for Windsor holiday homes

Fridge, microwave, oven, stovetop

Chic Farmhouse Decor | Deck w/View

Chic Farmhouse Decor | Deck w/View
Sunapee
10.0 out of 10, Exceptional, (57 reviews)
"Loved our stay and will definitely return!"
United States
Jenifer S.
The price is €343
includes taxes & fees
26 Apr - 27 Apr
Chic Farmhouse Decor | Deck w/View
Exterior detail

Brook Road Condo

Brook Road Condo
Goshen
8.8 out of 10, Excellent, (15 reviews)
"Location was great"
United States
Andrew P.
The price is €277
includes taxes & fees
6 May - 7 May
Brook Road Condo
TV, fireplace, computer monitors

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 €683
includes taxes & fees
27 Apr - 28 Apr
Elysium on Little Sunapee-Dock, Firepit, Trails
Exterior

Luxury Treehouse Near Mount Sunapee | Fireplace + Deck

Luxury Treehouse Near Mount Sunapee | Fireplace + Deck
Newbury
10.0 out of 10, Exceptional, (30 reviews)
"Outstanding host and property—clean, beautiful, and really unique. Can’t wait to return!"
United States
Austin G.
The price is €380
includes taxes & fees
27 Apr - 28 Apr
Luxury Treehouse Near Mount Sunapee | Fireplace + Deck
Interior

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Ludlow
9.8 out of 10, Exceptional, (85 reviews)
"We had a great stay at this home for a long weekend skiing at Okemo. "
United States
Lisa W.
The price is €259
includes taxes & fees
26 Apr - 27 Apr
Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Exterior

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, (22 reviews)
"The treehouse was the perfect place to unwind and relax for a few nights. Seeing the pines covered in snow out of every window was truly magical. Clean, well stocked, and everything was in good working order. "
United States
Ashley P.
The price is €321
includes taxes & fees
30 Apr - 1 May
Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River
Comfort Townhome | In-room dining

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 €255
includes taxes & fees
30 Apr - 1 May
Brook Road Condo
TV, offices

The Tower House | Hot Tub | Firepit | Dog-Friendly

The Tower House | Hot Tub | Firepit | Dog-Friendly
Killington
9.0 out of 10, Wonderful, (2 reviews)
"Great place, near everything and great customer service!!"
United States
Patrick B.
The price is €558
includes taxes & fees
26 Apr - 27 Apr
The Tower House | Hot Tub | Firepit | Dog-Friendly
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, (41 reviews)
"Very easy check in and out and clean home. Streets nearby can be hard to travel without 4 wheel drive. "
United States
Andrew O.
The price is €413
includes taxes & fees
24 Apr - 25 Apr
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
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, (21 reviews)
"Great home. The hosts were accessible and responded quickly to questions. Definitely will stay there again!"
United States
Ellen V.
@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee
Property grounds

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 €339
includes taxes & fees
4 May - 5 May
Lake Front Family Friendly Escape
Property grounds

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 €469
includes taxes & fees
26 Apr - 27 Apr
Large Killington Area Home | Sleeps 7 | Game Room
Property grounds

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, (108 reviews)
"We enjoyed our stay, the house was lovely and close to everything in Ludlow and Okemo."
United States
Hannah M.
The price is €272
includes taxes & fees
30 Apr - 1 May
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
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 €677
includes taxes & fees
27 Apr - 28 Apr
Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!
Interior

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

CozyDen - AC, Grill, Bike to Mountain, Porch!
Killington
9.0 out of 10, Wonderful, (2 reviews)
"Place was clean and location was great"
United States
Berni H.
The price is €233
includes taxes & fees
24 Apr - 25 Apr
CozyDen - AC, Grill, Bike to Mountain, Porch!
Dining

Charming Chester Farmhouse near Near VT Slopes

Charming Chester Farmhouse near Near VT Slopes
Chester Depot
9.6 out of 10, Exceptional, (19 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 €346
includes taxes & fees
28 Apr - 29 Apr
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, (16 reviews)
"This was a lovely, well-kept home in a great location to Okemo Mountain."
United States
Nancy F.
The price is €510
includes taxes & fees
5 May - 6 May
New Ludlow Village Home with Stunning Okemo Mountain View
Exterior

Tranquil 3 bedroom Home with Hot Tub and Standby Generator in Andover

Tranquil 3 bedroom Home with Hot Tub and Standby Generator in Andover
Andover
The price is €459
includes taxes & fees
28 Apr - 29 Apr
Tranquil 3 bedroom Home with Hot Tub and Standby Generator in Andover
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 €394
includes taxes & fees
26 Apr - 27 Apr
Bear`s Den in Ludlow, Okemo Views + Epic Game Room
Terrace/patio

SugarBear- Pool, AC, Sauna, Gym, Tennis!

SugarBear- Pool, AC, Sauna, Gym, Tennis!
The Woods
10.0 out of 10, Exceptional, (7 reviews)
"Great stay. Place was as advertised. Owners were very accommodating and helpful. Would stay there again. "
United States
John B.
SugarBear- Pool, AC, Sauna, Gym, Tennis!
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

Best Western West Lebanon-Hanover Hotel

Best Western West Lebanon-Hanover Hotel

10/10 Excellent
"Usually, when you book an airport hotel you expect compromises. Not so here. The rooms were clean and quiet. The staff was very helpful, but not intrusive. Also, I had never seen an automatic 24 hour coffee machine that made a decent cup of coffee. Now I have. Their coffee machine in the breakfast area was very impressive. I'll be back."
Schuyler 2-night trip
Posted 1 hour ago
Best Western West Lebanon-Hanover Hotel

Find out more about Windsor

Windsor Holiday Homes information

Number of reviews
344
Accommodation
790 Holiday Homes
Lowest Price
€233
Highest Price
€683