Holiday Homes in Windsor

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
20 Mar - 22 Mar
In two months
1 May - 3 May
In three months
29 May - 31 May
In four months
26 Jun - 28 Jun

Our top choices for Windsor holiday homes

Exterior detail

Brook Road Condo

Brook Road Condo
Goshen
8.8 out of 10, Excellent, (14 reviews)
"Location was great"
United States
Andrew P.
The price is €285
includes taxes & fees
8 Mar - 9 Mar
Brook Road Condo
Fridge, microwave, oven, stovetop

Chic Farmhouse Decor | Deck w/View

Chic Farmhouse Decor | Deck w/View
Sunapee
10.0 out of 10, Exceptional, (55 reviews)
"Loved our stay and will definitely return!"
United States
Jenifer S.
The price is €379
includes taxes & fees
16 Mar - 17 Mar
Chic Farmhouse Decor | Deck w/View
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, (21 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 €322
includes taxes & fees
8 Mar - 9 Mar
Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River
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 €594
includes taxes & fees
11 Mar - 12 Mar
Elysium on Little Sunapee-Dock, Firepit, Trails
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 €258
includes taxes & fees
16 Mar - 17 Mar
Brook Road Condo
Exterior

Unique Treehouse Near Mt Sunapee

Unique Treehouse Near Mt Sunapee
Newbury
10.0 out of 10, Exceptional, (28 reviews)
"Great stay. Had a wonderful time."
United States
Chris P.
The price is €393
includes taxes & fees
8 Mar - 9 Mar
Unique Treehouse Near Mt Sunapee
Exterior

Charming Lakefront Cottage on Lake Mascoma

Charming Lakefront Cottage on Lake Mascoma
Enfield
10.0 out of 10, Exceptional, (20 reviews)
"Couple day getaway, beautiful views right on the water plenty of windows, well stocked on house essentials"
United States
Stephanie V.
The price is €532
includes taxes & fees
10 Mar - 11 Mar
Charming Lakefront Cottage on Lake Mascoma
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, (20 reviews)
"Great home. The hosts were accessible and responded quickly to questions. Definitely will stay there again!"
United States
Ellen V.
The price is €389
includes taxes & fees
30 Mar - 31 Mar
@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 €295
includes taxes & fees
8 Mar - 9 Mar
Lake Front Family Friendly Escape
Interior

CozyDen-Location, Ski Off/Shuttle On!

CozyDen-Location, 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 €359
includes taxes & fees
17 Mar - 18 Mar
CozyDen-Location, Ski Off/Shuttle On!
Interior

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

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

Cozy Vermont Cabin · Mountain Views · Near Okemo

Cozy Vermont Cabin · Mountain Views · Near Okemo
Chester
10.0 out of 10, Exceptional, (3 reviews)
"We really enjoyed our stay at this home. It had everything we needed and was very comfortable. The countryside around this part of Vermont is beautiful. We found lots of great museums and restaurants. "
United States
Donald M.
The price is €928
includes taxes & fees
7 Apr - 8 Apr
Cozy Vermont Cabin · Mountain Views · Near Okemo
Dining

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 €415
includes taxes & fees
24 Mar - 25 Mar
Chester Farmhouse Ski Retreat near Slopes
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
9.4 out of 10, Exceptional, (6 reviews)
"Great location to walk into town."
United States
Carol G.
The price is €637
includes taxes & fees
7 Apr - 8 Apr
Charming 3-Bedroom House. Walk to Sunapee Harbor and Short Drive to Mt. Sunapee
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 €643
includes taxes & fees
23 Mar - 24 Mar
The Tower House | Hot Tub | Firepit | Dog-Friendly
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 €389
includes taxes & fees
7 Apr - 8 Apr
Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Fridge, microwave, oven, stovetop

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, (107 reviews)
"Had a wonderful stay. Clean,well kept and cozy."
United States
Edwin G.
The price is €389
includes taxes & fees
7 Apr - 8 Apr
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Property grounds

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 €637
includes taxes & fees
9 Mar - 10 Mar
Fun In Fun Out Ski Home: Main Floor. Renovated 3BR/2BA. Hot Tub.
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 €485
includes taxes & fees
24 Mar - 25 Mar
Large Killington Area Home | Sleeps 7 | Game Room
Outdoor spa tub

The Big Lebearski! Hot Tub, FirePlace!

The Big Lebearski! Hot Tub, FirePlace!
Killington
10.0 out of 10, Exceptional, (19 reviews)
"Great location and excellent hosts "
United States
Peter G.
The price is €780
includes taxes & fees
17 Mar - 18 Mar
The Big Lebearski! Hot Tub, FirePlace!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windsor Hotel Reviews

White River Inn and Suites

White River Inn and Suites

10/10 Excellent
"Good place. "
Samuel 1-night trip
Posted 11 hours ago
White River Inn and Suites

Find out more about Windsor

Windsor Holiday Homes information

Number of reviews
324
Accommodation
772 Holiday Homes
Lowest Price
€258
Highest Price
€928