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
13 Feb - 15 Feb
In two months
27 Mar - 29 Mar
In three months
24 Apr - 26 Apr
In four months
22 May - 24 May

Our top choices for Windsor holiday homes

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 HK$1,435
HK$2,336 total
includes taxes & fees
2 Feb - 3 Feb
Brook Road Condo
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 HK$1,053
HK$2,988 total
includes taxes & fees
5 Feb - 6 Feb
Lake Front Family Friendly Escape
Exterior detail

Brook Road Condo

Brook Road Condo
Goshen
8.8 out of 10, Excellent, (14 reviews)
"Nice place close to the mountain!"
United States
Kevin N.
The price is HK$1,326
HK$2,506 total
includes taxes & fees
2 Feb - 3 Feb
Brook Road Condo
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, (19 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 HK$1,404
HK$2,920 total
includes taxes & fees
9 Feb - 10 Feb
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 HK$1,566
HK$5,506 total
includes taxes & fees
3 Feb - 4 Feb
Elysium on Little Sunapee-Dock, Firepit, Trails
Exterior

Unique Treehouse Near Mt Sunapee – No Cleaning Fee

Unique Treehouse Near Mt Sunapee – No Cleaning Fee
Newbury
10.0 out of 10, Exceptional, (27 reviews)
"Great stay. Had a wonderful time."
United States
Chris P.
The price is HK$1,896
HK$3,513 total
includes taxes & fees
1 Feb - 2 Feb
Unique Treehouse Near Mt Sunapee – No Cleaning Fee
Fridge, microwave, oven, stovetop

Chic Farmhouse Decor | Deck w/View

Chic Farmhouse Decor | Deck w/View
Sunapee
10.0 out of 10, Exceptional, (51 reviews)
"Loved our stay and will definitely return!"
United States
Jenifer S.
The price is HK$1,716
HK$3,470 total
includes taxes & fees
1 Mar - 2 Mar
Chic Farmhouse Decor | Deck w/View
Fridge, microwave, oven, stovetop

Luxury Condo Tucked in the Heart of Killington

Luxury Condo Tucked in the Heart of Killington
Killington
9.0 out of 10, Wonderful, (2 reviews)
"Comfortable stay, great location. "
United States
Marjana
The price is HK$1,339
HK$3,057 total
includes taxes & fees
10 Feb - 11 Feb
Luxury Condo Tucked in the Heart of Killington
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, (19 reviews)
"Great home. The hosts were accessible and responded quickly to questions. Definitely will stay there again!"
United States
Ellen V.
The price is HK$1,716
HK$4,029 total
includes taxes & fees
24 Feb - 25 Feb
@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee
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 HK$2,013
HK$4,919 total
includes taxes & fees
3 Feb - 4 Feb
Large Killington Area Home | Sleeps 7 | Game Room
Interior

CozyDen-Location, Fireplace, Ski Off/Shuttle On!

CozyDen-Location, Fireplace, 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 HK$1,230
HK$2,888 total
includes taxes & fees
4 Feb - 5 Feb
CozyDen-Location, Fireplace, Ski Off/Shuttle On!
3 bedrooms, desk, iron/ironing board, travel cot

Blueberry Hill Escape | Pet Friendly | HotTub | AC

Blueberry Hill Escape | Pet Friendly | HotTub | AC
Bridgewater
9.6 out of 10, Exceptional, (17 reviews)
"Very nice home! Plenty of room for everyone and a short drive to the mountain! Perfect "
United States
Gerri B.
The price is HK$1,482
HK$4,360 total
includes taxes & fees
3 Feb - 4 Feb
Blueberry Hill Escape | Pet Friendly | HotTub | AC
Interior

King Size Master With Attached Bath,Pool Table, Open Kitchen,2 Full Baths

King Size Master With Attached Bath,Pool Table, Open Kitchen,2 Full Baths
Bethel
10.0 out of 10, Exceptional, (66 reviews)
"Very cozy, warm and inviting. Beds were all comfortable. House is big enough to have your own space yet intimate enough for pool, and family game night. Highly recommend!"
United States
Christine F.
The price is HK$1,257
HK$2,106 total
includes taxes & fees
11 Feb - 12 Feb
King Size Master With Attached Bath,Pool Table, Open Kitchen,2 Full Baths
Dining

Chester Farmhouse Ski Retreat near Slopes

Chester Farmhouse Ski Retreat near Slopes
Chester Depot
9.6 out of 10, Exceptional, (18 reviews)
"This was my second time staying at this property. Everything was great just like last year. I highly recommend it if you are staying in Chester, VT. "
United States
Lori N.
The price is HK$1,623
HK$3,268 total
includes taxes & fees
10 Feb - 11 Feb
Chester Farmhouse Ski Retreat near Slopes
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, (104 reviews)
"Had a wonderful stay. Clean,well kept and cozy."
United States
Edwin G.
The price is HK$1,874
HK$3,695 total
includes taxes & fees
2 Feb - 3 Feb
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Exterior

Charming Lakefront Cottage on Lake Mascoma

Charming Lakefront Cottage on Lake Mascoma
Enfield
10.0 out of 10, Exceptional, (20 reviews)
"Lovely location and beautiful well equipped house. "
United States
Anne S.
The price is HK$2,209
HK$4,606 total
includes taxes & fees
1 Feb - 2 Feb
Charming Lakefront Cottage on Lake Mascoma
Property grounds

Fun In Fun Out Ski Home: Upper Unit. Renovated 3BR/2BA. Hot Tub. Sauna.

Fun In Fun Out Ski Home: Upper Unit. Renovated 3BR/2BA. Hot Tub. Sauna.
Killington
10.0 out of 10, Exceptional, (2 reviews)
"This was a perfect property for our quick vacation. The house is very well equipped and you have everything you need for a relaxing fun stay in Killington. The hot tub was great, and the house is in a very convenient location while fairly private at the same time. We really enjoyed our stay and would definitely recommend staying here."
United States
Linda D.
Fun In Fun Out Ski Home: Upper Unit. Renovated 3BR/2BA. Hot Tub. Sauna.
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 HK$2,013
HK$5,721 total
includes taxes & fees
2 Feb - 3 Feb
The Tower House | Hot Tub | Firepit | Dog-Friendly
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 HK$4,907
HK$8,659 total
includes taxes & fees
1 Feb - 2 Feb
Cozy Vermont Cabin · Mountain Views · Near Okemo
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
9.2 out of 10, Wonderful, (5 reviews)
"Great location to walk into town."
United States
Carol G.
The price is HK$3,120
HK$5,755 total
includes taxes & fees
4 Feb - 5 Feb
Charming 3-Bedroom House. Walk to Sunapee Harbor and Short Drive to Mt. Sunapee
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

Summit Lodge

Summit Lodge

10/10 Excellent
"It's what you expect when you stay at an old ski lodge. It has a vibe. Totally would come here again. Very unique experience. Little rooms remind me of something out of Germany. "
Dominique 2-night trip
Posted 2 days ago
Summit Lodge

Find out more about Windsor

Windsor Vacation Homes information

Number of reviews
381
Accommodation
772 Vacation Homes
Lowest Price
HK$2,106
Highest Price
HK$8,659

Explore a world of travel with Expedia