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, (30)
"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 NZ$300
includes taxes & fees
20 Jan - 21 Jan 2026
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.

Brook Road Cabin

Brook Road Cabin
3.5 star property
Goshen
7.8 out of 10, Good, (9)
"In the aftermath of 30+” of snow we dug out and sought a new location with power and hot showers. How blessed we were to find this gem. A point of refuge and some much needed R&R. Cabin was quaint, warm, and comfortable, and the host was attentive and welcoming. Thank you for this port in the storm. 😊"
United States
Jill
Brook Road Cabin

Private Hot Tub Suite

Private Hot Tub Suite
Antrim
9.0 out of 10, Wonderful, (10)
"Stayed 3 nights while visiting relatives. Teen loved the Xbox. Had everything we could possibly need. Would definitely stay again."
United States
Dena S.
The price is NZ$442
includes taxes & fees
4 Jan - 5 Jan 2026
Private Hot Tub Suite

Relaxing Hot Tub Getaway

Relaxing Hot Tub Getaway
Antrim
9.6 out of 10, Exceptional, (15)
"The hot tub was great and the peace and quiet was very nice."
United States
Brian B.
The price is NZ$476
includes taxes & fees
30 Dec - 31 Dec
Relaxing Hot Tub Getaway

Lake Front Family Friendly Escape

Lake Front Family Friendly Escape
Newport
10.0 out of 10, Exceptional, (4)
"Great visit! The house is perfectly outfitted for a relaxing vacation. Super clean and updated. Really enjoyed the warm waters of Crescent Lake!"
United States
Ann R.
The price is NZ$685
includes taxes & fees
13 Jan - 14 Jan 2026
Lake Front Family Friendly Escape

Charming cabin in delightful Greenfield New Hampshire with WiFi access

Charming cabin in delightful Greenfield New Hampshire with WiFi access
Greenfield
9.8 out of 10, Exceptional, (9)
"Its was great clean, quite and comfortable. "
United States
John G.
The price is NZ$451
includes taxes & fees
5 Jan - 6 Jan 2026
Charming cabin in delightful Greenfield New Hampshire with WiFi access

Brook Road Condo

Brook Road Condo
Goshen
8.8 out of 10, Excellent, (14)
"Nice place close to the mountain!"
United States
Kevin N.
The price is NZ$554
includes taxes & fees
25 Dec - 26 Dec
Brook Road Condo

Downtown Hot Tub Escape

Downtown Hot Tub Escape
Keene
9.6 out of 10, Exceptional, (21)
"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 NZ$516
includes taxes & fees
30 Dec - 31 Dec
Downtown Hot Tub Escape

Book your ski vacations for the upcoming season.

Book your ski vacations for the upcoming season.
Sutton
10.0 out of 10, Exceptional, (9)
"House is very clean and comfortable. Kitchen well appointed, Nice location with view of Blaisdell Lake. Several state parks and Lake Sunapee nearby"
United States
Nancy B.
The price is NZ$658
includes taxes & fees
4 Jan - 5 Jan 2026
Book your ski vacations for the upcoming season.

Peaceful Private Lake Waterfront 8 min to skiing kayaks and hiking!

Peaceful Private Lake Waterfront 8 min to skiing kayaks and hiking!
2.0 star property
Bennington
The price is NZ$544
includes taxes & fees
7 Jan - 8 Jan 2026
Peaceful Private Lake Waterfront 8 min to skiing kayaks and hiking!

Room 10 - Queen Room

Room 10 - Queen Room
Francestown
10.0 out of 10, Exceptional, (1)
"Easy access to skiing Crotched mountain, great breakfast and dinner! Lovely people!"
United States
j l.
The price is NZ$362
includes taxes & fees
29 Dec - 30 Dec
Room 10 - Queen Room

Brook Road Condo

Brook Road Condo
3.0 star property
Goshen
8.8 out of 10, Excellent, (3)
"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 NZ$513
includes taxes & fees
22 Jan - 23 Jan 2026
Brook Road Condo

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, (18)
"We loved sitting by and listening to the river. Everything was as described."
United States
Jennifer A.
The price is NZ$687
includes taxes & fees
22 Jan - 23 Jan 2026
Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River

Brook Road Cabin

Brook Road Cabin
Goshen
9.8 out of 10, Exceptional, (17)
"Would go back!"
United States
Elizabeth C.
The price is NZ$554
includes taxes & fees
25 Dec - 26 Dec
Brook Road Cabin

Chic Farmhouse Decor | Deck w/View

Chic Farmhouse Decor | Deck w/View
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 NZ$780
includes taxes & fees
8 Jan - 9 Jan 2026
Chic Farmhouse Decor | Deck w/View

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, (16)
"Loved staying at this quaint cottage, the outside spaces were lovely and it was very clean! Communication with the owner was seamless and they were fantastic to deal with. I would highly recommend a stay here! "
United States
Lisa P.
The price is NZ$769
includes taxes & fees
5 Jan - 6 Jan 2026
Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee

Owl's Nest Treehouse

Owl's Nest Treehouse
Alstead
10.0 out of 10, Exceptional, (14)
"10/10 across the board! The cabin was a great experience. The hot tub was amazing. They have their own store near by with lots of goodies. They were very helpful with any questions we had. Would come here again!"
United States
Adriana
The price is NZ$577
includes taxes & fees
4 Jan - 5 Jan 2026
Owl's Nest Treehouse

Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston

Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston
Stoddard
10.0 out of 10, Exceptional, (1)
"Place was clean, cozy & very relaxing.. accommodating & communicative host provided us with necessary info for great week! Beautiful lake & landscape was great viewing during surprise snowstorm! Our Thanksgiving week was wonderful as we enjoyed lovely, quiet area in spacious 4 bdrm/2 bath home! Will definitely consider returning"
United States
Jeannie M.
The price is NZ$1,035
includes taxes & fees
25 Dec - 26 Dec
Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston

Ski Minutes Away & Pool Onsite

Ski Minutes Away & Pool Onsite
Henniker
10.0 out of 10, Exceptional, (9)
"Perfect location. We are attending a family wedding at Pat's Peak. Enjoyed this very comfortable home! Thank you!"
United States
Maria M.
The price is NZ$865
includes taxes & fees
30 Dec - 31 Dec
Ski Minutes Away & Pool Onsite

16 ppl 2 hot tubs, game room, fire pit

16 ppl 2 hot tubs, game room, fire pit
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 NZ$751
includes taxes & fees
8 Jan - 9 Jan 2026
16 ppl 2 hot tubs, game room, 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 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$451 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.