Windsor Holiday Rentals

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Holiday Rentals in Windsor

Owl's Nest Treehouse

Alstead
10.0 out of 10, Exceptional, (11)
"Great place . Would highly recommend it.!"
United States
Peter G.
The price is NZ$600
includes taxes & fees
18 Nov - 19 Nov
Owl's Nest Treehouse

Private Beach And Mountain Lake Home

Washington
9.6 out of 10, Exceptional, (124)
"This home is a fantastic gathering place, perfect for family time and making great memories! The home is very rustic and vintage which we all loved so much and the beach is just beautiful! Had everything needed for a comfortable stay, plenty of room and grounds are very nice. Washington is in the center of a lot of places to visit and things to do. We had so much fun and amazing quality time together, it was just truly awesome!"
United States
Jill W.
Private Beach And Mountain Lake Home

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

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

Private Hot Tub Suite

Antrim
9.0 out of 10, Wonderful, (10)
"The rental was very clean and spacious. Response was quick when i had a question. The purple king size mattresses were appreciated. Its hard to find king size mattresses in a rental let alone 2 good quality ones. Lots of little details to make your stay more enjoyable like a sound machine in the bedrooms and night light in the bathroom. Kitchen was fully stock so you can cook meals. I feel with the obesity rate more than 50% for americans the furniture and bed frames could be more sturdy. The...
United States
Nicole S.
The price is NZ$454
includes taxes & fees
11 Nov - 12 Nov
Private Hot Tub Suite

16 ppl 2 hot tubs, game room, fire pit

Antrim
9.8 out of 10, Exceptional, (9)
"Great place, everything and more as described online. Rebecca is a great host, very responsive and helpful. We really enjoyed our stay."
United States
Chris S.
The price is NZ$904
includes taxes & fees
18 Nov - 19 Nov
16 ppl 2 hot tubs, game room, fire pit

Charming cabin in delightful Greenfield New Hampshire with WiFi access

Greenfield
9.8 out of 10, Exceptional, (8)
The price is NZ$468
includes taxes & fees
15 Nov - 16 Nov
Charming cabin in delightful Greenfield New Hampshire with WiFi access

Quaint Dunbarton Waterfront Cottage

Dunbarton
9.4 out of 10, Exceptional, (56)
"Great time at this quite little getaway. It was a hidden gem!"
United States
Jennifer R.
Quaint Dunbarton Waterfront Cottage

Book your ski vacations for the upcoming season.

Sutton
10.0 out of 10, Exceptional, (9)
"The house exceeded all expectations. I can’t possibly say enough about this place. It’s perfectly located, perfectly clean, perfect layout. We didn’t have kids but had we, it would have felt extremely welcoming. Plenty of room, super clean, great temperature control inside, the bedding was top-notch, access to a grill…. Seriously awesome. The owners were excellent with communication. I’ve travelled the world and they, again, were top brass."
United States
Katherine C.
The price is NZ$687
includes taxes & fees
10 Nov - 11 Nov
Book your ski vacations for the upcoming season.

HISTORIC, RENOVATED BARN w/ Mt. SUNAPEE VIEW, SLEEPS 22+, Minutes to Lake / Mt.

Newbury
9.8 out of 10, Exceptional, (87)
"The house - or as it was referred to by some the castle - was awesome. We truly enjoyed our stay. "
United States
Marcia N.
HISTORIC, RENOVATED BARN w/ Mt. SUNAPEE VIEW, SLEEPS 22+, Minutes to Lake / Mt.

Harbor House: Sleeps 20, Fireplace, 2 TVs, 2 kitchens, walk to restaurants/bars

Sunapee
9.6 out of 10, Exceptional, (27)
"This space was great for our large family attending a nearby wedding. The large table and living space was exactly what we were hoping for. All bedrooms were comfortable and adequate. "
United States
Judy H.
Harbor House: Sleeps 20, Fireplace, 2 TVs, 2 kitchens, walk to restaurants/bars

Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.

Peterborough
9.8 out of 10, Exceptional, (28)
"My stay was what I wanted – quiet and time to study and pray. The town has many beautiful brick buildings and quaint shops for shopping. I thoroughly enjoyed my stay."
United States
Betty D.
The price is NZ$283
includes taxes & fees
18 Nov - 19 Nov
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.

Spacious Estate With Mtn Views! Private Setting, Great Family Home!!

Peterborough
10.0 out of 10, Exceptional, (71)
"There house is large and comfortable. Wayne was very helpful and accommodating. Highly recommend. "
United States
James T.
Spacious Estate With Mtn Views! Private Setting, Great Family Home!!

"Big Sky" Retreat Atop Sunapee / Ski + Lake Life

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 NZ$1,924
includes taxes & fees
19 Nov - 20 Nov
"Big Sky" Retreat Atop Sunapee / Ski + Lake Life

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

Newport
10.0 out of 10, Exceptional, (16)
"Will definitely be back"
United States
Lester T.
Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River

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

Newbury
10.0 out of 10, Exceptional, (16)
"My family and I stayed for a ski weekend up at Mount Sunapee. The house was perfect for our needs and just a quick 5 minutes from the mountain. The hosts had thought of everything and we had a great experience! We will be back!"
United States
Anne Marie R.
The price is NZ$801
includes taxes & fees
16 Nov - 17 Nov
Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee

Lake & Mountain Home - Walking distance to Sunapee Harbor

Sunapee
10.0 out of 10, Exceptional, (39)
"Gary’s Vrbo was perfect for our thanksgiving stay! Had plenty of room, kitchen was well stocked, and the fireplace was great!"
United States
Jenna B.
Lake & Mountain Home - Walking distance to Sunapee Harbor

SPACIOUS Custom 5 Bed Home Minutes to Mt.Sunapee! Garage, Hot Tub, Game Room!

Newbury
10.0 out of 10, Exceptional, (24)
"Great place to stay for a golf trip and boating on lake sunapee. Place is beautiful! "
United States
Tom M.
SPACIOUS Custom 5 Bed Home Minutes to Mt.Sunapee! Garage, Hot Tub, Game Room!

Peaceful Mountain View Retreat

Hancock
9.6 out of 10, Exceptional, (15)
"Perfect ski getaway. We loved Crotched Mountain and the peaceful retreat when we returned back to the property. "
United States
ANTHONY
Peaceful Mountain View Retreat

Sunapee Sunset Cottage | Grill | Fire Pit

2.0 star property
Newbury
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

Charming Lake Sunapee & Mt. Sunapee Ski Cabin

Newbury
9.6 out of 10, Exceptional, (23)
"This was a great location to Mt. Sunapee! Kitchen had everything we needed, beds were comfortable, and house was warm. Could use TV instructions, as remotes did not function. We enjoyed 4 nights, pretty low maintenance family, spent most of our time snowboarding. We brought our dog, and she loved it as she found a toy and we forgot to pack her one!"
United States
Diane R.
Charming Lake Sunapee & Mt. Sunapee Ski Cabin
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 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 NZ$283 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.