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Top 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 £415
includes taxes & fees
21 Jul - 22 Jul
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 £442
includes taxes & fees
24 Jul - 25 Jul
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 £187
includes taxes & fees
11 Aug - 12 Aug
Studio Suite #2 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 £189
includes taxes & fees
20 Jul - 21 Jul
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 £189
includes taxes & fees
29 Jul - 30 Jul
Studio Suite #9 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 £218
includes taxes & fees
23 Jul - 24 Jul
Studio Suite #4 at The Lodge | Minutes from Sunapee Harbor & Mount 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. "
Studio Suite #3 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 £377
includes taxes & fees
1 Aug - 2 Aug
Studio Suite #1 at The Lodge | Minutes from Sunapee Harbor & 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!"
1 Bed/1.5 Bath Suite #7 at The Lodge | Minutes from Sunapee Harbor & Mt. 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 £422
includes taxes & fees
21 Jul - 22 Jul
2 Bed/2 Bath Suite #5 at The Lodge | Minutes from Sunapee Harbor & Mt. 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 £208
includes taxes & fees
30 Jul - 31 Jul
Studio Suite #11 at The Lodge | Minutes from Sunapee Harbor and Mount Sunapee

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

9.8 out of 10, Exceptional, (8)
"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 £429
includes taxes & fees
31 Jul - 1 Aug
1 Bed/2 Bath Suite #6 at The Lodge | Minutes from Sunapee Harbor & Mt. Sunapee

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

10.0 out of 10, Exceptional, (1)
"Immaculate property and centrally located.Great communication with host."
The price is £512
includes taxes & fees
27 Jul - 28 Jul
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, (10)
"Great place, great host, great location!"
The price is £461
includes taxes & fees
21 Jul - 22 Jul
@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 £616
includes taxes & fees
4 Aug - 5 Aug
Main Street Retreat 4-bedroom w Hot Tub, Walk to Beach, Harbor & Restaurants

Brook Road Condo

3.0 star property
8.8 out of 10, Excellent, (3)
The price is £242
includes taxes & fees
20 Jul - 21 Jul
Brook Road Condo

Brook Road Condo

8.8 out of 10, Excellent, (14)
"Nice place close to the mountain!"
The price is £267
includes taxes & fees
20 Jul - 21 Jul
Brook Road Condo

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 £396
includes taxes & fees
24 Jul - 25 Jul
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 £671
includes taxes & fees
27 Jul - 28 Jul
Luxury Graduation Rental- Walk to Dartmouth!

Acres & Views! Firepit, BBQ | Bayley Way Getaway

The price is £505
includes taxes & fees
4 Aug - 5 Aug
Acres & Views! Firepit, BBQ | Bayley Way Getaway
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?

Quaint lakefront home with a private deck, firepit, and dock: This holiday home rental outside of Windsor is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games in this rental home to help you unwind.

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 Harpoon Brewery and Mt Ascutney State Park.

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.