Search Vacation 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 vacation 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 AED 654
AED 1,216 total
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 AED 790
AED 1,654 total
includes taxes & fees
15 Mar - 16 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 AED 661
AED 1,375 total
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 AED 663
AED 2,616 total
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 AED 676
AED 1,100 total
includes taxes & fees
8 Mar - 9 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 AED 909
AED 1,676 total
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 AED 1,098
AED 2,256 total
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 AED 643
AED 1,642 total
includes taxes & fees
25 Mar - 26 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 AED 397
AED 1,275 total
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 AED 722
AED 1,513 total
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
The price is AED 840
AED 2,044 total
includes taxes & fees
9 Mar - 10 Mar
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 AED 2,200
AED 3,941 total
includes taxes & fees
5 Apr - 6 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 AED 962
AED 1,765 total
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 AED 1,469
AED 2,734 total
includes taxes & fees
13 Mar - 14 Mar
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 AED 948
AED 2,777 total
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 AED 896
AED 1,722 total
includes taxes & fees
6 Apr - 7 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 AED 896
AED 1,722 total
includes taxes & fees
6 Apr - 7 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 AED 955
AED 2,655 total
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 AED 753
AED 2,069 total
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 AED 1,412
AED 3,360 total
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

Eid al-Fitr Sale

Members save up to 40% on hotels. Plan this year’s big trip and save.
Book now
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 1 hour ago
White River Inn and Suites

Explore a world of travel with Expedia