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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$1,436
HK$2,338 total
includes taxes & fees
9 Feb - 10 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$938
HK$2,857 total
includes taxes & fees
2 Mar - 3 Mar
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$1,327
HK$2,473 total
includes taxes & fees
10 Feb - 11 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$1,405
HK$2,922 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$1,470
HK$5,637 total
includes taxes & fees
1 Feb - 2 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$2,110
HK$3,764 total
includes taxes & fees
5 Feb - 6 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$1,547
HK$3,332 total
includes taxes & fees
4 Feb - 5 Feb
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$1,293
HK$3,007 total
includes taxes & fees
2 Feb - 3 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$1,719
HK$4,036 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$2,014
HK$4,922 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$1,113
HK$2,739 total
includes taxes & fees
2 Feb - 3 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$1,868
HK$4,857 total
includes taxes & fees
10 Feb - 11 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$1,258
HK$2,108 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$1,477
HK$3,072 total
includes taxes & fees
3 Mar - 4 Mar
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$1,842
HK$3,653 total
includes taxes & fees
4 Feb - 5 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$2,149
HK$4,502 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.
The price is HK$1,684
HK$5,208 total
includes taxes & fees
2 Feb - 3 Feb
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$2,430
HK$6,260 total
includes taxes & fees
10 Feb - 11 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$4,911
HK$8,779 total
includes taxes & fees
2 Feb - 3 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$3,122
HK$5,759 total
includes taxes & fees
22 Feb - 23 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.
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Top Windsor Hotel Reviews

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

10/10 Excellent
"Friendly staff, clean rooms. "
Kirt 1-night trip
Posted 3 days ago
Pointe at Castle Hill Resort

Find out more about Windsor

Windsor Vacation Homes information

Number of reviews
382
Accommodation
772 Vacation Homes
Lowest Price
HK$2,108
Highest Price
HK$8,779

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