Windsor Holiday Rentals

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Our top choices for Windsor holiday rentals

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

Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Peterborough
9.8 out of 10, Exceptional, (33 reviews)
"Fully equipped kitchen, comfortable open floor plan, easy walk to downtown and very hospitable—thank you—we’d like to stay here again next year!"
United States
Mark
The price is AU$229
includes taxes & fees
16 Mar - 17 Mar
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.

Cozy & Bright Guest Suite

Cozy & Bright Guest Suite
Peterborough
The price is AU$305
includes taxes & fees
10 Mar - 11 Mar
Cozy & Bright Guest Suite

Quiet Cabin rental near Pat's Peak - Seacoast

Quiet Cabin rental near Pat's Peak - Seacoast
Henniker
10.0 out of 10, Exceptional, (2 reviews)
"Adorable place! Excellent job removing snow during a storm. We will definitely return!"
United States
Meg V.
The price is AU$306
includes taxes & fees
10 Mar - 11 Mar
Quiet Cabin rental near Pat's Peak - Seacoast

Relaxing Hot Tub Getaway

Relaxing Hot Tub Getaway
Antrim
9.4 out of 10, Exceptional, (16 reviews)
"We wanted a place where we could eat and spend time together while still having space for everyone else to stretch out and this hit all the right buttons. Family weekend to visit our grandson, a student at nearby NEC, After a 3 hour drive up from the Cape, followed by an afternoon at the mall and restocking his dorm room, the hot tub was just what the doctor ordered!Rebecca is a wonderful host, very responsive, friendly, and helpful!"
United States
Jean C.
The price is AU$367
includes taxes & fees
11 Mar - 12 Mar
Relaxing Hot Tub Getaway

Private Hot Tub Suite

Private Hot Tub Suite
Antrim
9.0 out of 10, Wonderful, (10 reviews)
"Host was communicative and helpful with some specific questions we had. The apartment was in a cute older house, nicely updated and set up for guests. Everything was nicely labeled to be easy to find. The hot tub was great as well!"
United States
Sarah H.
The price is AU$367
includes taxes & fees
12 Mar - 13 Mar
Private Hot Tub Suite

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

Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River
Newport
9.8 out of 10, Exceptional, (21 reviews)
"The tree house was just as pictured, beautiful inside and we had great views of the River. It was a great trip and we look forward to coming back!"
United States
Kimberly R.
The price is AU$528
includes taxes & fees
10 Mar - 11 Mar
Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River

Peaceful Family Friendly Private Lake Waterfront Home 8 Min to Skiing & Hiking

Peaceful Family Friendly Private Lake Waterfront Home 8 Min to Skiing & Hiking
Bennington
10.0 out of 10, Exceptional, (11 reviews)
"Good 2-bedroom cabin close to Crotched skiing/boarding. Scenic frozen lake views. Cozy beds. Nice!"
United States
Matthew
The price is AU$520
includes taxes & fees
10 Mar - 11 Mar
Peaceful Family Friendly Private Lake Waterfront Home 8 Min to Skiing & Hiking

Brook Road Condo

Brook Road Condo
Goshen
8.8 out of 10, Excellent, (14 reviews)
"Location was great"
United States
Andrew P.
The price is AU$465
includes taxes & fees
15 Mar - 16 Mar
Brook Road Condo

Modern Downtown 12ppl Hot Tub Fire Pit Games

Modern Downtown 12ppl Hot Tub Fire Pit Games
Keene
9.6 out of 10, Exceptional, (22 reviews)
"Good location for some event staff to stay while we were hosting a conference in town. Simple check-in/out. Would rent again."
United States
Jack P.
The price is AU$430
includes taxes & fees
12 Mar - 13 Mar
Modern Downtown 12ppl Hot Tub Fire Pit Games

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

Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee
Newbury
10.0 out of 10, Exceptional, (18 reviews)
"We loved our weekend experience at the Hideaway! "
United States
Benjamin M.
The price is AU$639
includes taxes & fees
10 Mar - 11 Mar
Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee

Chic Farmhouse Decor | Deck w/View

Chic Farmhouse Decor | Deck w/View
Sunapee
10.0 out of 10, Exceptional, (55 reviews)
"Loved our stay and will definitely return!"
United States
Jenifer S.
The price is AU$632
includes taxes & fees
15 Mar - 16 Mar
Chic Farmhouse Decor | Deck w/View

Owl's Nest Treehouse

Owl's Nest Treehouse
Alstead
10.0 out of 10, Exceptional, (19 reviews)
"We loved our stay at The Owls Nest! The location was very private, and everything was exceptionally clean. Perfect for a quick weekend getaway to relax. Would highly recommend for a couple looking to enjoy a quiet weekend. "
United States
Samantha R.
The price is AU$482
includes taxes & fees
11 Mar - 12 Mar
Owl's Nest Treehouse

Charming 16x16 pine cabin in delightful Greenfield New Hampshire with WiFi

Charming 16x16 pine cabin in delightful Greenfield New Hampshire with WiFi
Greenfield
10.0 out of 10, Exceptional, (13 reviews)
"Charming location and beautiful setting. "
United States
Cherie G.
The price is AU$345
includes taxes & fees
15 Mar - 16 Mar
Charming 16x16 pine cabin in delightful Greenfield New Hampshire with WiFi

Unique Treehouse Near Mt Sunapee

Unique Treehouse Near Mt Sunapee
Newbury
10.0 out of 10, Exceptional, (28 reviews)
"Great stay. Had a wonderful time."
United States
Chris P.
The price is AU$644
includes taxes & fees
10 Mar - 11 Mar
Unique Treehouse Near Mt Sunapee

Brook Road Cabin

Brook Road Cabin
Goshen
9.8 out of 10, Exceptional, (17 reviews)
"Would go back!"
United States
Elizabeth C.
The price is AU$479
includes taxes & fees
15 Mar - 16 Mar
Brook Road Cabin

Spring Ski vacation bookings are here and NH Maple Weekend!

Spring Ski vacation bookings are here and NH Maple Weekend!
Sutton
10.0 out of 10, Exceptional, (19 reviews)
"Perfect house for our stay!"
United States
Shelley R.
The price is AU$558
includes taxes & fees
10 Mar - 11 Mar
Spring Ski vacation bookings are here and NH Maple Weekend!

Ski Minutes Away & Pool Onsite

Ski Minutes Away & Pool Onsite
Henniker
10.0 out of 10, Exceptional, (9 reviews)
"A lovely place to stay while visiting the area for the weekend. Key pad check in was seamless, and communication with the host was top notch. Would recommend and stay here again!"
United States
Sarah A.
The price is AU$716
includes taxes & fees
10 Mar - 11 Mar
Ski Minutes Away & Pool Onsite

Room 10 - Queen Room

Room 10 - Queen Room
Francestown
10.0 out of 10, Exceptional, (1 review)
"Easy access to skiing Crotched mountain, great breakfast and dinner! Lovely people!"
United States
j l.
The price is AU$282
includes taxes & fees
16 Mar - 17 Mar
Room 10 - Queen Room

Brook Road Condo

Brook Road Condo
3.0 star property
Goshen
8.8 out of 10, Excellent, (3 reviews)
"Convenient location, quiet and rural. Accommodations were clean and neat. Nice to have full kitchen for meal prep and snacks."
United States
Margaret
The price is AU$426
includes taxes & fees
15 Mar - 16 Mar
Brook Road Condo

@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee

@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee
Sunapee
10.0 out of 10, Exceptional, (20 reviews)
"Great home. The hosts were accessible and responded quickly to questions. Definitely will stay there again!"
United States
Ellen V.
The price is AU$632
includes taxes & fees
30 Mar - 31 Mar
@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee
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$229 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?

HISTORIC, RENOVATED BARN w/ Mt. SUNAPEE VIEW, SLEEPS 22+, Minutes to Lake / Mt.: This holiday home rental outside of Windsor is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a library.

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.