Windsor Holiday Rentals

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Holiday Rentals in Windsor

Cabin in Alstead

10.0 out of 10, Exceptional, (13)
"Great place . Would highly recommend it.!"
United States
Peter G.
The price is AU$512
includes taxes & fees
14 Dec - 15 Dec
Owl's Nest Treehouse

Holiday Home in Weare

9.8 out of 10, Exceptional, (62)
"We enjoyed a fantastic week! The house is amazing and well appointed. So many fun activities and great for relaxation with the entire family. Grateful to our hosts and their responsiveness around any and all of our inquiries.We look forward to staying again."
United States
Kate Z.
Beautiful Private Lakefront new Log Home

Cabin in Greenfield

9.8 out of 10, Exceptional, (8)
"Its was great clean, quite and comfortable. "
United States
John G.
The price is AU$401
includes taxes & fees
9 Dec - 10 Dec
Charming cabin in delightful Greenfield New Hampshire with WiFi access

Holiday Home in Antrim

9.8 out of 10, Exceptional, (9)
"Clean, lots of space, helpful host, hot tub was also nice"
United States
Howard H.
The price is AU$613
includes taxes & fees
10 Dec - 11 Dec
16 ppl 2 hot tubs, game room, fire pit

Holiday Home in Washington

9.6 out of 10, Exceptional, (124)
"Just returned from a wonderful stay at this property. The house was clean and had everything you could need while on vacation. The pond was so clean and clear. We even saw a loon."
United States
Patricia K.
Private Beach And Mountain Lake Home

Holiday Home in Newbury

10.0 out of 10, Exceptional, (9)
"Very spacious, with beautiful amenities and very friendly hosts!"
United States
Matthew H.
The price is AU$1,535
includes taxes & fees
9 Dec - 10 Dec
Private Family Friendly Ski&Lake Getaway on 2 acres. Short walk to Lake Sunapee

Holiday Home in Sunapee

10.0 out of 10, Exceptional, (39)
"House was clean and spacious. Loved the location near the harbor. Great area to stay in. "
United States
Christine M.
Lake & Mountain Home - Walking distance to Sunapee Harbor

Chalet in Antrim

10.0 out of 10, Exceptional, (6)
"Perfect place for a quick getaway! Lovely house in a great location!"
United States
Johnna P.
Direct Waterfront, Year-Round, A-Frame Cabin

Holiday Home in Newbury

9.8 out of 10, Exceptional, (87)
"This property exceeded our expectations and provided an exceptional experience. Our stay was flawless-truly one of the most memorable vacations we’ve had. We thoroughly enjoyed cooking together, exploring the surrounding area, and unwinding in such a comfortable setting. Everything was thoughtfully arranged, and we wouldn’t change a thing. "
United States
Rebecca S.
HISTORIC, RENOVATED BARN w/ Mt. SUNAPEE VIEW, SLEEPS 22+, Minutes to Lake / Mt.

Holiday Home in Peterborough

10.0 out of 10, Exceptional, (72)
"The property was absolutely perfect. House was even better than the pictures with so much space to spread out with a large family. It is apparent that the owners take great pride in making it nice. Everything was spotless! The surrounding grounds were also beautiful."
United States
Kathleen S.
Spacious Estate With Mtn Views! Private Setting, Great Family Home!!

Holiday Home in Newbury

10.0 out of 10, Exceptional, (8)
"Great Stay. House is indeed a "Big Sky Retreat". Both Chrisn and Leah made the stay very comfortable. The hosts were very approachable whenever we had questions. We had agreat experience and recommend the property for everyone."
United States
Aditya A.
The price is AU$1,558
includes taxes & fees
15 Dec - 16 Dec
"Big Sky" Retreat Atop Sunapee / Ski + Lake Life

Holiday Home in Lempster

9.8 out of 10, Exceptional, (24)
"It was a great weekend of hanging out with the kids and grandkids"
United States
Cindy R.
Beautiful Waterfront , four season home on charming Crescent Lake!

Holiday Home in Newbury

2.0 star property
Spacious 3BR Home Near Lake & Mountain - Sleeps 9 - Sunapee Retreat

Holiday Home in Sunapee

9.0 out of 10, Wonderful, (4)
"Great location to walk into town."
United States
Carol G.
The price is AU$1,121
includes taxes & fees
16 Dec - 17 Dec
Charming 3-Bedroom House. Walk to Sunapee Harbor and Short Drive to Mt. Sunapee

Holiday Home in Newbury

10.0 out of 10, Exceptional, (24)
"The house was exactly what we needed. "
United States
David Z.
SPACIOUS Custom 5 Bed Home Minutes to Mt.Sunapee! Garage, Hot Tub, Game Room!

Holiday Home in Washington

10.0 out of 10, Exceptional, (128)
"Perfect little vaca cabin. Enjoyed our stay and time on the beach. Will definitely book again. "
United States
Mark K.
Log Home In Secluded Lake Ashuelot Estates

Holiday Home in Sunapee

10.0 out of 10, Exceptional, (51)
"This place is pristine and very cozy. Bed's are insanely comfortable too. Will definitely try to stay there again. "
United States
Peter S.
The price is AU$654
includes taxes & fees
9 Dec - 10 Dec
Chic Farmhouse Decor | Deck w/View

Cottage in Dunbarton

9.4 out of 10, Exceptional, (57)
"Great time at this quite little getaway. It was a hidden gem!"
United States
Jennifer R.
Quaint Dunbarton Waterfront Cottage

Holiday Home in Sunapee

10.0 out of 10, Exceptional, (21)
"Really comfortable place. Really enjoyed our stay..."
United States
Jon C.
SPACIOUS and PRIVATE renovated farmhouse for the whole family

Holiday Home in Newbury

2.0 star property
7.0 out of 10, Good, (2)
"Clean, simple, cozy, and great location. I have work and business related event in the area and my wife decide to join. She absolutely loved it and stayed there during our 5 day stay while I had business to handle. She loves being near the water and although the place was set back a little from the water... it was great for her and the time she spent there. We enjoyed the privacy and overall time we spent there. "
United States
Amer T.
Sunapee Sunset Cottage | Grill | Fire Pit
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

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, 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 favourite 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 depend 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 AU$401 per night. Entering your travel dates in the search wizard might find you 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.