Holiday Homes in Windsor

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Check prices for these dates

In two weeks
5 Sept - 7 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov
In four months
12 Dec - 14 Dec

Featured Holiday Homes in Windsor

Our top choices for Windsor holiday homes

Relaxing Hot Tub Getaway
Smart TV, fireplace, video games, ping pong

Relaxing Hot Tub Getaway

9.6 out of 10, Exceptional, (14)
"The hot tub was great and the peace and quiet was very nice."
The price is AU$427
includes taxes & fees
24 Aug - 25 Aug
Relaxing Hot Tub Getaway
Private Hot Tub Suite
Terrace/patio

Private Hot Tub Suite

10.0 out of 10, Exceptional, (7)
"very nice, very clean, beautiful place, quiet location."
The price is AU$399
includes taxes & fees
24 Aug - 25 Aug
Private Hot Tub Suite
Studio Suite #4 at The Lodge | Minutes from Sunapee Harbor & Mount Sunapee
Dining

Studio Suite #4 at The Lodge | Minutes from Sunapee Harbor & Mount Sunapee

10.0 out of 10, Exceptional, (12)
"What a great place to stay at Sunapee. Great location, amenities, clean and what a view! Thank you to the hosts :)"
The price is AU$314
includes taxes & fees
24 Aug - 25 Aug
Studio Suite #4 at The Lodge | Minutes from Sunapee Harbor & Mount Sunapee
Lake Front Family Friendly Escape
Fridge, microwave, oven, stovetop

Lake Front Family Friendly Escape

10.0 out of 10, Exceptional, (3)
"What an amazing place! Very serene, clean and big enough for my family of 5. The hosts thought of everything to make our stay comfortable and memorable. Tough to beat the location! We will absolutely return!"
The price is AU$652
includes taxes & fees
9 Sept - 10 Sept
Lake Front Family Friendly Escape
@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee
Dining

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

2.0 star property
10.0 out of 10, Exceptional, (13)
"Great place, great host, great location!"
The price is AU$809
includes taxes & fees
16 Sept - 17 Sept
@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee
Studio Suite #3 at The Lodge | Minutes from Sunapee Harbor & Mount Sunapee
Property grounds

Studio Suite #3 at The Lodge | Minutes from Sunapee Harbor & Mount Sunapee

10.0 out of 10, Exceptional, (4)
"Beautiful views"
The price is AU$334
includes taxes & fees
21 Sept - 22 Sept
Studio Suite #3 at The Lodge | Minutes from Sunapee Harbor & Mount Sunapee
Charming year round 2 bedroom 2 bath house.
Interior

Charming year round 2 bedroom 2 bath house.

10.0 out of 10, Exceptional, (6)
"Very close and easy drive to Sunapee Mountain. Garage was available to store our ski gear. House was perfect size for 3 friends. Host was very communicative and helpful. Great View of the lake as well."
The price is AU$677
includes taxes & fees
2 Sept - 3 Sept
Charming year round 2 bedroom 2 bath house.
“Big Red” @ New London/Sunapee | Lake-Ski-Wellness
TV, fireplace, DVD player, books

“Big Red” @ New London/Sunapee | Lake-Ski-Wellness

10.0 out of 10, Exceptional, (13)
"Fantastic property and host! An excellent home base for skiing at Mt. Sunapee. Especially loved the hot tub and fire pit."
The price is AU$1,486
includes taxes & fees
24 Aug - 25 Aug
“Big Red” @ New London/Sunapee | Lake-Ski-Wellness
16 ppl 2 hot tubs, game room, fire pit
Terrace/patio

16 ppl 2 hot tubs, game room, fire pit

9.8 out of 10, Exceptional, (8)
"Clean, lots of space, helpful host, hot tub was also nice"
The price is AU$937
includes taxes & fees
26 Aug - 27 Aug
16 ppl 2 hot tubs, game room, fire pit
Charming 3-Bedroom House. Walk to Sunapee Harbor and Short Drive to Mt. Sunapee
Smart TV, video games, books

Charming 3-Bedroom House. Walk to Sunapee Harbor and Short Drive to Mt. Sunapee

9.4 out of 10, Exceptional, (3)
"Walk to the harbor clean roomy house"
The price is AU$1,047
includes taxes & fees
4 Sept - 5 Sept
Charming 3-Bedroom House. Walk to Sunapee Harbor and Short Drive to Mt. Sunapee
Cozy Home Near Downtown, Shops, and Restaurants.
Exterior

Cozy Home Near Downtown, Shops, and Restaurants.

2.0 star property
10.0 out of 10, Exceptional, (7)
"This was just a few minutes drive from the city of Keene and was a perfect family rental. It had everything we needed. "
The price is AU$856
includes taxes & fees
25 Aug - 26 Aug
Cozy Home Near Downtown, Shops, and Restaurants.
"Big Sky" Retreat Atop Sunapee / Ski + Lake Life
Interior

"Big Sky" Retreat Atop Sunapee / Ski + Lake Life

10.0 out of 10, Exceptional, (6)
"We had the most amazing stay at Leah and Chris’s beautiful home! From the moment we arrived, we were blown away by how clean, spacious, and thoughtfully stocked the house was—it truly had everything we could possibly need and more.Our group of 12 (including young kids and dogs!) had tons of space to spread out comfortably, and every single bed was super cozy. The huge yard was perfect for lawn games, which were conveniently provided, and we spent hours outside enjoying the privacy and peaceful...
The price is AU$1,738
includes taxes & fees
16 Sept - 17 Sept
"Big Sky" Retreat Atop Sunapee / Ski + Lake Life
Chic Farmhouse Decor | Deck w/View
Fridge, microwave, oven, stovetop

Chic Farmhouse Decor | Deck w/View

10.0 out of 10, Exceptional, (51)
"Great cabin about 2 minutes from Mt. Sunapee resort and state park, as well as several lake towns. Beds are extra comfortable and the kitchen has everything we needed. "
The price is AU$706
includes taxes & fees
8 Sept - 9 Sept
Chic Farmhouse Decor | Deck w/View
Downtown Hot Tub Escape
Fridge, microwave, oven, stovetop

Downtown Hot Tub Escape

9.6 out of 10, Exceptional, (17)
"Property was easy to locate. The rooms were perfect! Hot tub was fantastic! "
The price is AU$659
includes taxes & fees
24 Aug - 25 Aug
Downtown Hot Tub Escape
Main Street Retreat 4-bedroom w Hot Tub, Walk to Beach, Harbor & Restaurants
Fridge, microwave, oven, stovetop

Main Street Retreat 4-bedroom w Hot Tub, Walk to Beach, Harbor & Restaurants

10.0 out of 10, Exceptional, (2)
"Great location. Fun weekend. House nicely maintained and supplied. "
The price is AU$1,181
includes taxes & fees
2 Sept - 3 Sept
Main Street Retreat 4-bedroom w Hot Tub, Walk to Beach, Harbor & Restaurants
Private Family Friendly Ski&Lake Getaway on 2 acres. Short walk to Lake Sunapee
Exterior

Private Family Friendly Ski&Lake Getaway on 2 acres. Short walk to Lake Sunapee

10.0 out of 10, Exceptional, (8)
"Very spacious, with beautiful amenities and very friendly hosts!"
The price is AU$1,623
includes taxes & fees
24 Aug - 25 Aug
Private Family Friendly Ski&Lake Getaway on 2 acres. Short walk to Lake Sunapee
Cobb Meadow House - Cozy 5 Bedroom New England home in The Monadnock Region
Interior

Cobb Meadow House - Cozy 5 Bedroom New England home in The Monadnock Region

10.0 out of 10, Exceptional, (23)
"Good place to stay during a wedding week"
The price is AU$1,125
includes taxes & fees
26 Aug - 27 Aug
Cobb Meadow House - Cozy 5 Bedroom New England home in The Monadnock Region
Boutique Cottage | Patio & Fire Pit | Deck w/ View
Exterior

Boutique Cottage | Patio & Fire Pit | Deck w/ View

10.0 out of 10, Exceptional, (101)
"Very nice place and very nice hosts. Would definitely stay again!"
The price is AU$1,297
includes taxes & fees
4 Sept - 5 Sept
Boutique Cottage | Patio & Fire Pit | Deck w/ View
Unique Treehouse Near Mt Sunapee – No Cleaning Fee
Exterior

Unique Treehouse Near Mt Sunapee – No Cleaning Fee

10.0 out of 10, Exceptional, (25)
"We loved our stay at this house! So special and memorable. We can’t wait to come back. "
The price is AU$831
includes taxes & fees
25 Aug - 26 Aug
Unique Treehouse Near Mt Sunapee – No Cleaning Fee
1 Bed/1.5 Bath Suite #10 at The Lodge | Minutes from Sunapee Harbor & Mt Sunapee
Fridge, microwave, dishwasher, coffee/tea maker

1 Bed/1.5 Bath Suite #10 at The Lodge | Minutes from Sunapee Harbor & Mt Sunapee

10.0 out of 10, Exceptional, (1)
"This place was wonderful. It was clean, comforting, and had everything we needed! I think we found our new place to get away to! The host was helpful and responded very quickly to Amy messages."
The price is AU$453
includes taxes & fees
24 Aug - 25 Aug
1 Bed/1.5 Bath Suite #10 at The Lodge | Minutes from Sunapee Harbor & 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

The Burrell House

The Burrell House

10/10 Excellent
"Beautiful room, beautiful house, fun area!"
Susannah 1-night trip
Posted 2 days ago
The Burrell House