Photo by William E Berry Jr.

Search Vacation Homes in Windsor

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Vacation Homes in Windsor

Beautiful home offering privacy on 7 acres with private pond

West Windsor
10.0 out of 10, Exceptional, (30)
"Lots of space inside and out for my family to enjoy here! The sunny living room with its many windows brings the outside indoors."
United States
Eileen W.
The price is AED 747
AED 1,787 total
includes taxes & fees
16 Nov - 17 Nov
Beautiful home offering privacy on 7 acres with private pond

Brook Road Condo

3.0 star property
Goshen
8.8 out of 10, Excellent, (3)
"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 632
AED 1,052 total
includes taxes & fees
16 Nov - 17 Nov
Brook Road Condo

@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee

2.0 star property
Sunapee
10.0 out of 10, Exceptional, (18)
"We greatly enjoyed a quick get away to this beautiful sun-filled house! The house was exceptionally clean and comfortable, very relaxing place to stay! "
United States
Jonathan G.
The price is AED 562
AED 1,582 total
includes taxes & fees
19 Nov - 20 Nov
@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee

Lake Front Family Friendly Escape

Newport
10.0 out of 10, Exceptional, (4)
"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 463
AED 1,355 total
includes taxes & fees
16 Nov - 17 Nov
Lake Front Family Friendly Escape

Whimsical Room & Private Bathroom in Historic Inn

Chester Depot
8.8 out of 10, Excellent, (9)
"The room was really cozy and the community area was quaint and comfortable. "
United States
Bethany
The price is AED 294
AED 535 total
includes taxes & fees
16 Nov - 17 Nov
Whimsical Room & Private Bathroom in Historic Inn

Brook Road Condo

Goshen
8.8 out of 10, Excellent, (14)
"Nice place close to the mountain!"
United States
Kevin N.
The price is AED 591
AED 1,140 total
includes taxes & fees
16 Nov - 17 Nov
Brook Road Condo

The Carol - 10 minutes to Okemo & Newly Renovated

Cavendish
10.0 out of 10, Exceptional, (6)
"Perfect place for a weekend ski trip to Okemo. The host was very helpful!"
United States
Thomas G.
The Carol - 10 minutes to Okemo & Newly Renovated

Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit

Bridgewater
9.4 out of 10, Exceptional, (16)
"It was a great location for what we were looking to do. Great size and we loved the hot tub. Very comfortable. We enjoyed our stay and would come again"
United States
Ashley G.
The price is AED 503
AED 1,802 total
includes taxes & fees
16 Nov - 17 Nov
Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit

Luxury Condo Tucked in the Heart of Killington

Killington
8.0 out of 10, Very Good, (1)
"The condo was in a beautiful location but was rather isolated from grocery and dining options. Our host was good at communicating however we received a message about the fireplace not being available to us a day before we came and we got there in the dark with no lights on. The condo itself could not really be called "luxury" as it was dated and lacked some basics like soap in the bathroom, a towel hook in the 1/2 bath, kleenex, cracked dishes, etc. Liked that it was near a waterfall and hiking...
United States
Dean
The price is AED 436
AED 1,185 total
includes taxes & fees
16 Nov - 17 Nov
Luxury Condo Tucked in the Heart of Killington

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

Killington
10.0 out of 10, Exceptional, (1)
"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 317
AED 1,027 total
includes taxes & fees
17 Nov - 18 Nov
CozyDen-Location, Fireplace, Ski Off/Shuttle On!

Chic Farmhouse Decor | Deck w/View

Sunapee
10.0 out of 10, Exceptional, (51)
"We were very pleased with our stay. The house was very clean and matched the description exactly. Comfortable beds — the mattresses were excellent! Very close to Mount Sunapee. "
United States
Bonnie H.
The price is AED 760
AED 1,606 total
includes taxes & fees
17 Nov - 18 Nov
Chic Farmhouse Decor | Deck w/View

Mountain Stay | Skiing | Hiking | Sleeps 8

Bridgewater
9.6 out of 10, Exceptional, (7)
"Very large place for 6 to 8 people. Great location between Woodstock and Killington. Lots of living spaces and great king-size beds and mattresses"
United States
frank
The price is AED 698
AED 1,987 total
includes taxes & fees
15 Nov - 16 Nov
Mountain Stay | Skiing | Hiking | Sleeps 8

TheGrizz! Shuttle on/off!

Killington
10.0 out of 10, Exceptional, (4)
"We went to Killington to ski and we were pleasantly surprised at how close everything was. The drive distance to the ski lifts and the access road for apres was minutes. Dan & Holly were super informative about everything and easy to communicate with the whole time we were there. Fabulous accommodations, very comfortable and very clean with all the comforts of home."
United States
Beth R.
The price is AED 377
AED 1,571 total
includes taxes & fees
18 Nov - 19 Nov
TheGrizz! Shuttle on/off!

Bearmont- Pool, HotTub, Fireplace

The Woods
10.0 out of 10, Exceptional, (6)
"Great location and a great place. Felt right at home"
United States
Tyler B.
The price is AED 417
AED 1,741 total
includes taxes & fees
17 Nov - 18 Nov
Bearmont- Pool, HotTub, Fireplace

180-degree panoramic views of Vermont's mountains from the Living room, Hot Tub

Hartford
10.0 out of 10, Exceptional, (1)
"The house was absolutely beautiful. A unique mix of modern and 70’s. The layout was spot on . We were only there one night , a very quick stop over but it was so comfortable and cozy. The host was so easy to communicate with and was very accommodating. Plenty of room to sleep a large group and the views….you have to see in person. Stunning . I travel a lot and use VRBO for all of my travels. This was one of the best experiences I have had . I recommend 100%. "
United States
Mary Anne C.
The price is AED 661
AED 1,511 total
includes taxes & fees
17 Nov - 18 Nov
180-degree panoramic views of Vermont's mountains from the Living room, Hot Tub

Unique Treehouse Near Mt Sunapee – No Cleaning Fee

Newbury
10.0 out of 10, Exceptional, (26)
"We loved our stay at this house! So special and memorable. We can’t wait to come back. "
United States
Robin L.
The price is AED 988
AED 1,774 total
includes taxes & fees
16 Nov - 17 Nov
Unique Treehouse Near Mt Sunapee – No Cleaning Fee

Charming Lakefront Cottage on Lake Mascoma

Enfield
10.0 out of 10, Exceptional, (19)
"We really enjoyed our stay at the lake! The house is updated and well appointed, and seems like it was recently renovated. Excellent views and access to the lake. We really loved this home and will be back to stay again! "
United States
Blair P.
The price is AED 1,010
AED 2,136 total
includes taxes & fees
16 Nov - 17 Nov
Charming Lakefront Cottage on Lake Mascoma

Chester Farmhouse Ski Retreat near Slopes

Chester Depot
9.6 out of 10, Exceptional, (15)
"Great cozy home for our trip to Vermont. Very comfortable. Recommend walking over to country girl dinner and the Scottish pub."
Canada
Benjamin M.
The price is AED 547
AED 1,283 total
includes taxes & fees
16 Nov - 17 Nov
Chester Farmhouse Ski Retreat near Slopes

Peaceful oasis, stunning views, less than 10 mins from Woodstock Village

Pomfret
10.0 out of 10, Exceptional, (3)
"Enjoyed the cleanliness and the convenience of being close to Woodstock, and not too far from Stowe."
United States
Dee Dee H.
The price is AED 551
AED 1,399 total
includes taxes & fees
11 Dec - 12 Dec
Peaceful oasis, stunning views, less than 10 mins from Woodstock Village

Fun In Fun Out Ski Home: Main Floor. Renovated 3BR/2BA. Hot Tub.

2.0 star property
Killington
10.0 out of 10, Exceptional, (1)
"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 695
AED 2,095 total
includes taxes & fees
17 Nov - 18 Nov
Fun In Fun Out Ski Home: Main Floor. Renovated 3BR/2BA. Hot Tub.
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Windsor Hotel Reviews