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Top Holiday Rentals in Windsor

Our top choices for Windsor holiday rentals

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 £253
includes taxes & fees
2 Sept - 3 Sept
Owl's Nest Treehouse

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

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 £346
includes taxes & fees
3 Sept - 4 Sept
Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee

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

9.2 out of 10, Wonderful, (50)
"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

9.6 out of 10, Exceptional, (5)
The price is £201
includes taxes & fees
1 Sept - 2 Sept
Charming cabin in delightful Greenfield New Hampshire with WiFi access

"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 £845
includes taxes & fees
1 Sept - 2 Sept
"Big Sky" Retreat Atop Sunapee / Ski + Lake Life

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!

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!

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

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 £294
includes taxes & fees
2 Sept - 3 Sept
Downtown Hot Tub Escape

Cozy & bright getaway close to ski mountains and lake

10.0 out of 10, Exceptional, (29)
"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

10.0 out of 10, Exceptional, (12)
"Will definitely be back"
Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River

Perfect Lake or Mountain Getaway Less Than 5 Minutes Away

10.0 out of 10, Exceptional, (19)
"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

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

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

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

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

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 £329
includes taxes & fees
8 Sept - 9 Sept
Unique Cozy private 1-bedroom apartment in charming Temple

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!
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

Find out more about Windsor

Find out more about Windsor

Everything you need to know about Windsor holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Windsor holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windsor. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windsor holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windsor holiday rentals we have selected for you start as low as £201 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Windsor?

Yes, there are holiday rentals close to the most popular sights in Windsor, or you can select a more secluded option if you're looking for a relaxing stay.

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

Private Beach And Mountain Lake Home: This holiday home rental outside of Windsor is located on the beach, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals will I find in Windsor?

Expedia has 5 holiday 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 wider area, you’ll find Windsor Town Hall and Franklin Pierce Homestead.

What’s a holiday rental in Windsor like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Windsor. Holiday rentals provide amenities such as hot tubs, fire pits and patios so you'll have a home away from home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of safety 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 hotel, which is another reason why a holiday rental is a popular option for a family trip.