Windsor Vacation Rentals

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Sep 3 - Sep 4
Tomorrow
Sep 4 - Sep 5
This weekend
Sep 5 - Sep 7
Next weekend
Sep 12 - Sep 14

Vacation Rentals in Windsor

Our top choices for Windsor vacation rentals

Owl's Nest Treehouse
Property grounds

Owl's Nest Treehouse

10.0 out of 10, Exceptional, (7)
"Treehouse was just as the pictures and description portray. It was clean, quiet and peaceful. My wife and I stayed at the Owl's Nest Treehouse for just a quick one night get away. It was the perfect spot for some quiet time alone and a soak in the hot tub. The check in process was as simple as it gets, and the owners were very responsive to the few questions we asked. For dinner we went to Springfield VT (about a 30 min drive). You can probably find something a little closer, but Alstead...
The price is ￥40,475
￥49,346 total
includes taxes & fees
Sep 7 - Sep 8
Owl's Nest Treehouse
Private Beach And Mountain Lake Home
Miscellaneous

Private Beach And Mountain Lake Home

9.6 out of 10, Exceptional, (121)
"We had a wonderful stay! The house was very clean and comfortable and the area is beautiful!"
Private Beach And Mountain Lake Home
Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee
Private kitchen

Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee

10.0 out of 10, Exceptional, (16)
"We loved our stay here. House was very tidy, property owner easy to communicate with, and location great right by the lake and mountain. There are also a few nice hikes nearby. "
The price is ￥30,466
￥69,785 total
includes taxes & fees
Sep 16 - Sep 17
Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee
"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 ￥71,529
￥170,709 total
includes taxes & fees
Sep 16 - Sep 17
"Big Sky" Retreat Atop Sunapee / Ski + Lake Life
Charming Lake Sunapee & Mt. Sunapee Ski Cabin
Exterior

Charming Lake Sunapee & Mt. Sunapee Ski Cabin

9.6 out of 10, Exceptional, (23)
"Great get away on lake Sunapee, great house just a short walk to the lake. Great place to relax and take in the sun set on the dock or grilling on the deck. Well equipped home that is super clean,just a great getaway. "
Charming Lake Sunapee & Mt. Sunapee Ski Cabin
Quaint Dunbarton Waterfront Cottage
Property grounds

Quaint Dunbarton Waterfront Cottage

9.4 out of 10, Exceptional, (51)
"This property was perfect for us. My wife and 2 sons had a fantastic time. We were in New Hampshire for my sons college graduation. It was perfect for us. We had a beautiful weekend on the lake. It could not have been better!! Thank you for the memories!!"
Quaint Dunbarton Waterfront Cottage
Charming cabin in delightful Greenfield New Hampshire with WiFi access
Interior

Charming cabin in delightful Greenfield New Hampshire with WiFi access

9.6 out of 10, Exceptional, (5)
The price is ￥17,815
￥27,383 total
includes taxes & fees
Sep 4 - Sep 5
Charming cabin in delightful Greenfield New Hampshire with WiFi access
Happy Place On Lake Sunapee - 10 minutes from the ski resort
Outdoor dining

Happy Place On Lake Sunapee - 10 minutes from the ski resort

9.6 out of 10, Exceptional, (51)
"We LOVED this place! The house was stocked with all of the essentials, including towels and linens. This made traveling there easier. The swimming area was great too!"
Happy Place On Lake Sunapee - 10 minutes from the ski resort
Cozy cabin nestled in the woods, 5 minutes to Sunapee Mountain & lake!
Exterior

Cozy cabin nestled in the woods, 5 minutes to Sunapee Mountain & lake!

10.0 out of 10, Exceptional, (24)
"Clean cute cabin close to ski area well equipped with good living space. "
Cozy cabin nestled in the woods, 5 minutes to Sunapee Mountain & lake!
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 ￥30,286
￥55,251 total
includes taxes & fees
Sep 4 - Sep 5
Downtown Hot Tub Escape
Spectacular Log Home with Private Lake Access
TV, books, music library, video library

Spectacular Log Home with Private Lake Access

10.0 out of 10, Exceptional, (104)
"The property was great! Very clean and had everything we needed to cook meals and just relax. Lake was nice but it was a little chilly over the weekend. The hosts left some muffins, cookies, fruit and some beverages which was we though was a nice touch."
Spectacular Log Home with Private Lake Access
Cozy & bright getaway close to ski mountains and lake
Exterior

Cozy & bright getaway close to ski mountains and lake

10.0 out of 10, Exceptional, (30)
"This cozy cottage was perfect for our recent visit to visit family in Elkins, NH. It is located a short walk to Pleasant Lake for swimming and boating (in good weather). Steph was so attentive and helpful and provided many wonderful amenities in the cottage. This is our go-to place to stay whenever we visit the area."
Cozy & bright getaway close to ski mountains and lake
Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River
Exterior

Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River

10.0 out of 10, Exceptional, (12)
"Will definitely be back"
Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River
Lakefront Cabin/ 314' Shoreline
Exterior

Lakefront Cabin/ 314' Shoreline

10.0 out of 10, Exceptional, (2)
"This was a great place to disconnect with technology and reconnect with family. We had a great time."
Lakefront Cabin/ 314' Shoreline
Lake Sunapee Cozy Cottage - Blodgett Landing
Property grounds

Lake Sunapee Cozy Cottage - Blodgett Landing

9.6 out of 10, Exceptional, (50)
"We truly enjoyed the chance to escape from a busy city week and relax at Lake Sunapee on their dock, play games in the cottage, and going for a moderate hike on Mt. Kearsarge!"
Lake Sunapee Cozy Cottage - Blodgett Landing
Perfect Lake or Mountain Getaway Less Than 5 Minutes Away
Fridge, microwave, oven, stovetop

Perfect Lake or Mountain Getaway Less Than 5 Minutes Away

10.0 out of 10, Exceptional, (20)
"Came up for our annual golf trip, house was great! Plenty of room for our group. The house had everything we needed, just wish we had better weather to take advantage of the outdoor setup. Would highly recommend if you’re looking for a nice peaceful getaway."
Perfect Lake or Mountain Getaway Less Than 5 Minutes Away
Inviting Condo w Fire Place & Hot Tub
Outdoor spa tub

Inviting Condo w Fire Place & Hot Tub

9.6 out of 10, Exceptional, (5)
"We enjoyed staying here. It was a great condo and had everything we needed. The owners answered all our questions. The area was beautiful. I would stay here again."
Inviting Condo w Fire Place & Hot Tub
Waterfront Log Cabin with Mt. Sunapee Views
Exterior

Waterfront Log Cabin with Mt. Sunapee Views

10.0 out of 10, Exceptional, (59)
"We absolutely loved this lake house! The lake is crystal clear and the views of mt Sunapee were spectacular."
Waterfront Log Cabin with Mt. Sunapee Views
Amazing Mt. Sunapee Region Home Convenient for many activities! Winter Is Open!
Exterior

Amazing Mt. Sunapee Region Home Convenient for many activities! Winter Is Open!

9.8 out of 10, Exceptional, (161)
"We love the house, it had everything we needed!"
Amazing Mt. Sunapee Region Home Convenient for many activities! Winter Is Open!
Unique Cozy private 1-bedroom apartment in charming Temple
Terrace/patio

Unique Cozy private 1-bedroom apartment in charming Temple

9.4 out of 10, Exceptional, (3)
"What a lovely, family-friendly gem! The setting was peaceful with birds singing and dodging around the trees. The lodging was unusually well supplied and the decorations had innumerable personal touches. This would be a fabulous place to relax in peace or enjoy time together with family. "
The price is ￥51,513
￥62,918 total
includes taxes & fees
Sep 8 - Sep 9
Unique Cozy private 1-bedroom apartment in charming Temple
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windsor Hotel Reviews

Find out more about Windsor

Find out more about Windsor

Search for holiday rentals in Windsor on Expedia! You can easily find your home rentals, villas, holiday apartments in Windsor using one of the methods below:

  • View our selection of featured holiday rentals in Windsor
  • Use the map to find apartments and other holiday homes in the Windsor neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Windsor while they last

Look no further and take a look at our great range of rental properties in Windsor!

Frequently asked questions

Can I find a vacation rental in Windsor?

Yes, you can find vacation rentals near well known attractions in Windsor, or you can go with a more remote option if you're looking for relaxation.

What's the top vacation rental in Windsor?

Private Beach And Mountain Lake Home: You might like this vacation home rental near Windsor. It is located on the beach and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals will I find in Windsor?

Expedia has 5 vacation rentals for your stay in Windsor.

What’s there to see and do in Windsor?

Explore the area and family-friendly sights such as Eaton's Magic Morsel, or get out into nature at a spot like Black Pond. In the larger area, you’ll find Windsor Town Hall and Franklin Pierce Homestead.

What’s a vacation rental in Windsor like?

A vacation rental is a private property where you can stay for a few weeks or just a few days in Windsor. Vacation rentals provide amenities like kitchens and laundry facilities so your stay will be comfortable. If you're concerned about cleanliness, a vacation rental can offer a sense of safety away from public hotel elevators and busy lobbies while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular choice for small groups.