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Vacation Homes in Windsor

Beautiful home offering privacy on 7 acres with private pond
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.
$434 nightly
The price is $487
Nov 5 - Nov 6
Total with taxes and fees
Beautiful home offering privacy on 7 acres with private pond
Lake Front Family Friendly Escape
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.
$343 nightly
The price is $372
Nov 5 - Nov 6
Total with taxes and fees
Lake Front Family Friendly Escape
Whimsical Room & Private Bathroom in Historic Inn
8.8 out of 10, Excellent, (9)
"The room was really cozy and the community area was quaint and comfortable. "
United States
Bethany
$149 nightly
The price is $167
Nov 6 - Nov 7
Total with taxes and fees
Whimsical Room & Private Bathroom in Historic Inn
Brook Road Condo
3.0 star property
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
$264 nightly
The price is $286
Nov 5 - Nov 6
Total with taxes and fees
Brook Road Condo
CozyDen-Location, Fireplace, Ski Off/Shuttle On.
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.
$247 nightly
The price is $280
Nov 5 - Nov 6
Total with taxes and fees
CozyDen-Location, Fireplace, Ski Off/Shuttle On.
Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit
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.
$438 nightly
The price is $491
Nov 5 - Nov 6
Total with taxes and fees
Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit
Chic Farmhouse Decor | Deck w/View
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.
$392 nightly
The price is $426
Nov 5 - Nov 6
Total with taxes and fees
Chic Farmhouse Decor | Deck w/View
Luxury Condo Tucked in the Heart of 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
$308 nightly
The price is $327
Nov 5 - Nov 6
Total with taxes and fees
Luxury Condo Tucked in the Heart of Killington
Brook Road Condo
8.8 out of 10, Excellent, (14)
"Nice place close to the mountain!"
United States
Kevin N.
$288 nightly
The price is $312
Nov 5 - Nov 6
Total with taxes and fees
Brook Road Condo
Mountain Stay | Save 10% This Week Only | Hiking
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
$494 nightly
The price is $553
Nov 5 - Nov 6
Total with taxes and fees
Mountain Stay | Save 10% This Week Only | Hiking
Unique Treehouse Near Mt Sunapee – No Cleaning Fee
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.
$424 nightly
The price is $460
Nov 5 - Nov 6
Total with taxes and fees
Unique Treehouse Near Mt Sunapee – No Cleaning Fee
@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee
2.0 star property
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.
$407 nightly
The price is $442
Nov 11 - Nov 12
Total with taxes and fees
@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee
Bearmont- Pool, HotTub, Fireplace
10.0 out of 10, Exceptional, (6)
"Great location and a great place. Felt right at home"
United States
Tyler B.
$416 nightly
The price is $471
Nov 5 - Nov 6
Total with taxes and fees
Bearmont- Pool, HotTub, Fireplace
Powder Park Place: Lower Unit. Cozy and close to the Mountain! Discounted ski rentals.
10.0 out of 10, Exceptional, (2)
"A very comfortable stay for a family of four. Close to everything, clean, well stocked for breakfast making, and just enough room for everyone. We really enjoyed the fireplace after a day of skiing.Not sure why the heat setting turned to low 60s every night, but our blankets were warm."
United States
Maria K.
$364 nightly
The price is $411
Nov 5 - Nov 6
Total with taxes and fees
Powder Park Place: Lower Unit. Cozy and close to the Mountain! Discounted ski rentals.
Fun In Fun Out Ski Home: Main Floor. Renovated 3BR/2BA. Hot Tub.
2.0 star property
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.
$479 nightly
The price is $541
Nov 5 - Nov 6
Total with taxes and fees
Fun In Fun Out Ski Home: Main Floor. Renovated 3BR/2BA. Hot Tub.
TheGrizz! Shuttle on/off!
10.0 out of 10, Exceptional, (4)
"Couldn’t be any closer to the mountain without living on it. Base lodges are 1-2 min drive from the grounds. The room and amenities were perfect. It was very clean and comfortable. Climate control was simple with three thermostats. Kitchen had everything you would need. Fireplace was a nice touch. We didn’t get a chance to use the pool, gym etc. The app with all the neccesaary information for our stay was comprehensive and very useful. I would definitely return."
United States
MICHAEL F.
$377 nightly
The price is $426
Nov 5 - Nov 6
Total with taxes and fees
TheGrizz! Shuttle on/off!
180-degree panoramic views of Vermont's mountains from the Living room, Hot Tub
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.
$419 nightly
The price is $473
Dec 2 - Dec 3
Total with taxes and fees
180-degree panoramic views of Vermont's mountains from the Living room, Hot Tub
Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace
2.0 star property
$337 nightly
The price is $381
Nov 5 - Nov 6
Total with taxes and fees
Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace
Breakaway House: Renovated Killington Duplex, Unit A. Close to Resort.
7.6 out of 10, Good, (4)
"We stayed for 3 nights in early Feb '24. Great location, nice neighborhood & property w/ comfortable furniture. The kitchen was well stock w/ plates/glassware. The place was clean - the kitchen floor could use a mopping. The firewood needs better protection, it's damp & doesn't maintain a burn. The back sliding door doesn't lock - a 2x4 is used instead. The major issue is the radiant floor heating isn't sufficient it takes too long to adjust. We were very uncomfortable & didn't get much sleep...
United States
Charlie V.
$517 nightly
The price is $584
Nov 5 - Nov 6
Total with taxes and fees
Breakaway House: Renovated Killington Duplex, Unit A. Close to Resort.
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
9.8 out of 10, Exceptional, (103)
"A lovely time enjoying the off-season in a ski town. "
United States
Ed C.
$374 nightly
The price is $404
Nov 5 - Nov 6
Total with taxes and fees
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
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

Find out more about Windsor

Windsor Vacation Homes information

Number of reviews
251
Accommodation
762 Vacation Homes
Lowest Price
$167
Highest Price
$584

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