Photo by William E Berry Jr.

Windsor Holiday Rentals

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Holiday Rentals in Windsor

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 NZ$1,410
includes taxes & fees
14 July - 15 July
Unique Treehouse Near Mt Sunapee – No Cleaning Fee

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 NZ$783
includes taxes & fees
30 June - 1 July
Chic Farmhouse Decor | Deck w/View

Studio Suite #2 at The Lodge | Minutes from Sunapee Harbor & Mount Sunapee

9.8 out of 10, Exceptional, (6)
"Was a great location close to the mountain, comfortable and clean, an excellent stay. Walls were a bit thin, but others on property were respectful and quiet. Really enjoyed our stay for a weekend!"
The price is NZ$435
includes taxes & fees
29 June - 30 June
Studio Suite #2 at The Lodge | Minutes from Sunapee Harbor & Mount Sunapee

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 NZ$401
includes taxes & fees
29 June - 30 June
Studio Suite #4 at The Lodge | Minutes from Sunapee Harbor & Mount Sunapee

Studio Suite #1 at The Lodge | Minutes from Sunapee Harbor & Mount Sunapee

10.0 out of 10, Exceptional, (6)
"It’s always quiet and peaceful "
The price is NZ$355
includes taxes & fees
29 June - 30 June
Studio Suite #1 at The Lodge | Minutes from Sunapee Harbor & Mount Sunapee

Studio Suite #8 at The Lodge | Minutes from Sunapee Harbor and Mount Sunapee

9.8 out of 10, Exceptional, (6)
"The property was very clean. I would stay here again."
The price is NZ$509
includes taxes & fees
22 July - 23 July
Studio Suite #8 at The Lodge | Minutes from Sunapee Harbor and Mount Sunapee

Studio Suite #9 at The Lodge | Minutes from Sunapee Harbor & Mount Sunapee

10.0 out of 10, Exceptional, (25)
"The cabin was perfect. Had everything we might need. Loved the room, views, location, and game room. Thanks so much "
The price is NZ$408
includes taxes & fees
8 July - 9 July
Studio Suite #9 at The Lodge | Minutes from Sunapee Harbor & Mount Sunapee

2 Bed/2 Bath Suite #5 at The Lodge | Minutes from Sunapee Harbor & Mt. Sunapee

9.8 out of 10, Exceptional, (12)
"Nice clean property.10-15 minutes from Mt. Sunapee.Nice bedrooms and the gameroom was a bonus for our kids."
The price is NZ$826
includes taxes & fees
22 July - 23 July
2 Bed/2 Bath Suite #5 at The Lodge | Minutes from Sunapee Harbor & Mt. Sunapee

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

10.0 out of 10, Exceptional, (3)
"Beautiful property. Room was a perfect size for 2 people. Immaculate. Bed very comfortable. Gorgeous view. "
The price is NZ$509
includes taxes & fees
22 July - 23 July
Studio Suite #3 at The Lodge | Minutes from Sunapee Harbor & Mount Sunapee

Studio Suite #11 at The Lodge | Minutes from Sunapee Harbor and Mount Sunapee

10.0 out of 10, Exceptional, (4)
"Awesome place 😎 "
The price is NZ$452
includes taxes & fees
30 June - 1 July
Studio Suite #11 at The Lodge | Minutes from Sunapee Harbor and Mount Sunapee

1 Bed/1.5 Bath Suite #7 at The Lodge | Minutes from Sunapee Harbor & Mt. Sunapee

10.0 out of 10, Exceptional, (4)
"Very clean, beautiful views and easy to get into town!"
The price is NZ$609
includes taxes & fees
8 July - 9 July
1 Bed/1.5 Bath Suite #7 at The Lodge | Minutes from Sunapee Harbor & Mt. Sunapee

1 Bed/2 Bath Suite #6 at The Lodge | Minutes from Sunapee Harbor & Mt. Sunapee

9.8 out of 10, Exceptional, (7)
"It was wonderful trip! The property was beautiful and clean. This was our second time staying at the lodge. Always a great experience! "
The price is NZ$609
includes taxes & fees
29 June - 30 June
1 Bed/2 Bath Suite #6 at The Lodge | Minutes from Sunapee Harbor & Mt. Sunapee

Quaint lakefront; firepit, boat, kayaks, paddleboard, grill, laundry, hammock

9.8 out of 10, Exceptional, (8)
"The house is beautiful and the host is AWESOME!"
The price is NZ$1,403
includes taxes & fees
12 July - 13 July
Quaint lakefront; firepit, boat, kayaks, paddleboard, grill, laundry, hammock

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

The price is NZ$969
includes taxes & fees
7 July - 8 July
Charming 3-Bedroom House. Walk to Sunapee Harbor and Short Drive to Mt. Sunapee

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

2.0 star property
10.0 out of 10, Exceptional, (8)
"Great place, great host, great location!"
The price is NZ$1,008
includes taxes & fees
2 July - 3 July
@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee

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

10.0 out of 10, Exceptional, (1)
"Very clean and well designed rental. The owner was very pleasant to work with. I would highly recommend this rental to anyone!!"
The price is NZ$1,270
includes taxes & fees
9 July - 10 July
Main Street Retreat 4-bedroom w Hot Tub, Walk to Beach, Harbor & Restaurants

Lake Front Family Friendly Escape

10.0 out of 10, Exceptional, (2)
"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 NZ$674
includes taxes & fees
30 June - 1 July
Lake Front Family Friendly Escape

Luxury Graduation Rental- Walk to Dartmouth!

10.0 out of 10, Exceptional, (1)
"Amazing house within walking distance of the campus. Would definitely recommend to anyone."
The price is NZ$1,477
includes taxes & fees
27 July - 28 July
Luxury Graduation Rental- Walk to Dartmouth!

WhiSki Cabin - 12 Acres With a Mountain View!

10.0 out of 10, Exceptional, (3)
"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. "
The price is NZ$1,624
includes taxes & fees
10 July - 11 July
WhiSki Cabin - 12 Acres With a Mountain View!
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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Frequently asked questions

Can I find a holiday rental in Windsor?

Yes, there are holiday rentals in Windsor close to The Sustainable Farmer, or you can select a more secluded option if you're looking for a relaxing stay. Windsor is known for its breweries and golf courses. Make sure you have time to check out the forests while you're in the area.

What are some of the best holiday rentals that Windsor has to offer?

Okemo Mountain Lodging: This holiday home rental outside Windsor is in the mountains, and equipped with daily housekeeping and an LCD TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a dishwasher and a stovetop.

How many holiday rentals are there in Windsor?

With 9 Expedia holiday rentals, you're guaranteed to find just the right place for your Windsor stay.

What can I see and do in Windsor?

Connecticut River and Paradise Park are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include The Sustainable Farmer. Other places in town to visit include American Precision Museum and Harpoon Brewery.

What are holiday rentals like in Windsor?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windsor. Holiday rentals feature amenities such as patios, hot tubs and fire pits to help you enjoy your stay. If you're concerned about a clean environment, a holiday rental can offer a sense of privacy away from public hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular option for a family trip or a small group gathering.