Windsor Holiday Rentals from AU$183: Search Short-Term Rentals

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

Beutiful 3 bedroom upper unit of duplex home : This holiday home rental outside of Windsor is located by the ocean, and has a patio, a private garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

Check prices for these dates

Tonight

Tomorrow

Next weekend

In two weeks

Holiday Rentals in Windsor

Relax on the balcony overlooking a serene body of water with a scenic view of the surrounding landscape.

"Awesome stay"

includes taxes & fees

20 July - 21 July

Cozy retreat with a bed, pillows, and a throw blanket, surrounded by rustic wooden accents.

includes taxes & fees

20 July - 21 July

Enjoy outdoor dining and cooking on the deck, surrounded by trees and a serene lake view.

"Cabin is in a very quiet area, but still close to all stores/shopping you may need. Nice quiet lake."

includes taxes & fees

21 July - 22 July

Enjoy cooking in this well-equipped kitchen with a dining table and stainless steel appliances.

"It was amazing time ! "

Cozy retreat with a bed and wall-mounted light fixture.

includes taxes & fees

26 July - 27 July

Relax on the balcony with two comfortable sofas and a small table, taking in the serene views of the surrounding forest.

"Loved the sound of the loons on the lake, cozy accommodations and the beautiful scenery. Nice place, 10/10 "

includes taxes & fees

13 Aug - 14 Aug

Enjoy a serene beach scene with a sandy shore and calm waters.

"We had a great time!"

Relax on the deck with a table, two chairs, and a sofa, surrounded by trees.

"Excellent location and excellent host. Comfortable accommodations. "

Enjoy a serene view of the water from this deck, surrounded by trees and a distant shoreline.

"We liked this place, calm, beautiful nature!"

includes taxes & fees

20 July - 21 July

Stroll out to the covered porch, supported by white columns, and take in the serene surroundings.

"Location is perfect. Parking is easy. Close to shops, grocery, wineries, etc."

includes taxes & fees

20 July - 21 July

Stunning two-story home with a gabled roof, surrounded by a lush garden and vibrant greenery.

"Great overnight rental!"

includes taxes & fees

20 July - 21 July

Relax on the deck with a view of the surrounding landscape and water.

"This location is very comfortable - a home away from home. Loved the ocean view and the beautiful esthetic throughout the inn."

Stunning two-story residence with a deck and garden.

"Great location and accomodations. Will stay again."

includes taxes & fees

28 July - 29 July

Relax on the balcony with a wicker sofa and armchair, taking in the serene views of the surrounding forest.

includes taxes & fees

18 Aug - 19 Aug

Efficient kitchen with microwave, coffee maker, and stove, perfect for cooking and meal prep.

"i have really enjoyed the property it was clean and was exactly what we were looking for...the location for our golfing 4 days was great...it could use a bbq. the tv system is deplorable no news and barely any sports"

includes taxes & fees

27 July - 28 July

Relax in style with lounge chairs and a small table on this outdoor deck.

"Beautiful and clean spot, equipped with everything you need. "

Relax in a tranquil outdoor space with a wooden deck, wicker chairs, and a view of the surrounding forest.

includes taxes & fees

13 Aug - 14 Aug

Cozy space with a fireplace, bookshelf, and comfortable chair.

"Loved everything. All amenities provided. Very comfortable and clean. Would definitely go back! "

Relax in a cozy cabin with a swing bed suspended from a sturdy frame, surrounded by nature.

includes taxes & fees

20 July - 21 July

Relax in a spacious bathroom with a bathtub, wooden bench, and table with a lamp.

"Great stay. Will definitely be back!"

includes taxes & fees

20 July - 21 July

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Windsor Hotel Reviews

The Breeze Motel

10/10 Excellent

"Great place to stay if wanting to tour around Wolfville. Beach views are beautiful! Unit was clean and sufficient!"

Acadia University

10/10 Excellent

"This is a pretty solid choice for affordable summer travel accommodations with one big issue. It's a standard single dorm room with a bed, desk and wardrobe. There's a shared bathroom - two of them - and we were there with very few other people so there was no issue with waiting. There is a kitchenette with a fridge/freezer which we used to freshen up our cooler ice packs. What's the issue? There's no air conditioning and no fans. And when we were there Nova Scotia was in the grips of a heat wave. We went out and bought a fan from a local hardware store so we could sleep. The good news is we were there only one night and we are now up one portable fan. That said, parking was right by the building and the downtown strip was within walking distance (5-10 min). It's a great option, but book when the temperature isn't in the 30s, bring your own fan or prepare to sweat."

The Inn at Grand Pre Winery

10/10 Excellent

"Outstanding. Grand Pré Winery has mastered the impressive balance of being a top notch, well established, high end winery while still maintaining the ambiance, humbleness, pride and a genuine personal touch of a what can see is a quiet & real deal true family run passion. By staying in the Inn, we felt welcomed into the winery famiy for the time we were there. The old farm house has been so elegantly renovated to warm and comfotable living spaces while keeping that feeling of a good old fashion farm house. Of special not, Amanda, who provided our tour and tasting was incredibly delightful and so knowledgeable who showed such passion and pride at being part of the Grand Pré team. For that matter all staff were freindly, welcoming and just there at the right times making sure our stay or visits on the winery grounds were absolutely perfect. We met a quiet lovely lady working dilligently in the gardens as early as 7am every morning like clockwork and spent the morning tending to the gardens making sure theywere just right. When complementing this soft spoken woman on her hard work and beautiful gardens, we learned that she was in fact the wife of husband/wife team owners. So imlressive. The depth and breath of this well established winery offers an incredible range of exquisite wines whether it be of the White, Red, Rosé sparkling, ice wine and even some Cider surprises that you wont want to miss. A definie must do when visiting the Anapolis valley NS."

Treeside Retreat with Hot tub

10/10 Excellent

"This treeside cabin in the woods was absolutely perfect in every sense. The property and everything provided was top notch and it has spoiled us for future stays. I can’t say enough about this home. The beds and pillows were so comfy that we found out where they were from and ordered the same. The hot tub was wonderful. I would definitely recommend staying here and we will return! Thanks Brendan. The only downside was that we had to leave. "

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$183 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

Are there holiday rentals in Windsor?

Yes, there are holiday rentals in Windsor close to Windsor Hockey Heritage Centre, or you can select a more secluded option if you're looking for a relaxing stay. Windsor is known for its architecture and museums. Make sure you have time to check out the festivals and riverfront during your trip.

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

Beutiful 3 bedroom upper unit of duplex home: This holiday home rental outside of Windsor is located by the ocean, and has a patio, a private garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

What can I see and do in Windsor?

Cultural attractions include West Hants Historical Society and Haliburton House Museum, whereas Windsor Hockey Heritage Centre is just one of the family-friendly sights. Other places in town to visit include Fort Edward National Historic Site and Mermaid Theatre of Nova Scotia.

What are holiday rentals like in Windsor?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windsor. Holiday rentals offer extras such as WiFi and washers and dryers so you'll feel right at home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of seclusion away from public hotel lifts and busy concierge desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for family gatherings.

Members save 10% or more on over 100,000 hotels worldwide when you’re signed in

Windsor Holiday Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Holiday Rentals in Windsor

Micro Boutique Living Wolfville

Micro Boutique Living Wolfville

Sunken Escapes Bunny Cabin #10

Sunken Escapes Bunny Cabin #10

Archie's Lakeside Cabin

Archie's Lakeside Cabin

Treeside Retreat with Hot tub

Treeside Retreat with Hot tub

Sunken Escapes Fox Cabin #8

Sunken Escapes Fox Cabin #8

Sunken Escapes Kenny's (Unit 5)

Sunken Escapes Kenny's (Unit 5)

Cottage at Evangeline Beach & near Local Wineries

Cottage at Evangeline Beach & near Local Wineries

Beautiful Downtown Core Apt. Located on Main Street, Kentville

Beautiful Downtown Core Apt. Located on Main Street, Kentville

CAIA Lakeside Retreat- Sunken Lake, NS

CAIA Lakeside Retreat- Sunken Lake, NS

In the Heart of Town - Private Ground Level Unit

In the Heart of Town - Private Ground Level Unit

Darling downtown micro suite!

Darling downtown micro suite!

Beautiful Oceanfront Home on the Minas Basin

Beautiful Oceanfront Home on the Minas Basin

Wolfville at your Doorstep

Wolfville at your Doorstep

Sunken Escapes Glamping Unit 4

Sunken Escapes Glamping Unit 4

Beautiful 2 bedroom residential home in Kentville

Beautiful 2 bedroom residential home in Kentville

Chalet Drive - Lakefront Cottage

Chalet Drive - Lakefront Cottage

Sunken Escapes Glamping Unit #2

Sunken Escapes Glamping Unit #2

Bright, central location. Walking to all amenities.

Bright, central location. Walking to all amenities.

Sunken Escapes ZEEK (Unit 6)

Sunken Escapes ZEEK (Unit 6)

Gaspereau Suite - 2 Seat Jacuzzi, KingBd, Downtown

Gaspereau Suite - 2 Seat Jacuzzi, KingBd, Downtown

Top Windsor Hotel Reviews

The Breeze Motel

Find out more about Windsor

Find out more about Windsor

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Trending destinations on Expedia.com.au

Frequently asked questions