Holiday Rentals Windsor from £96: Find Short-Term Rentals & Holiday Accommodations

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

2 bedroom residential home in Kentville : This holiday home rental outside of Windsor is located by the ocean, and offers a private garden, WiFi and a Smart TV to help you feel perfectly comfortable in your new surroundings.

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In two weeks

In two months

In three months

In four months

Our top choices for Windsor holiday rentals

A bedroom with a bed, a nightstand, a chair, a window with curtains, a wall-mounted mirror, and a framed picture.

1. Gateway to Annapolis Valley | Windsor Studio Suite

Windsor

Michael

includes taxes & fees

13 Oct - 14 Oct

A corner room with a TV, a clock, a sofa, a lamp, and a view of buildings through the window.

2. Stylish Windsor Suite Near Wineries & Fundy Coast

Windsor

Lucie

includes taxes & fees

19 Oct - 20 Oct

A bedroom with a large bed, white pillows, and a view of a body of water through a sliding glass door.

3. Micro Boutique Living Wolfville

Wolfville

Kelly

includes taxes & fees

27 Oct - 28 Oct

4. Good place to call home for a week or so

Ellershouse

includes taxes & fees

9 Oct - 10 Oct

A spacious indoor area with a wooden floor, a dining table with chairs, and a kitchen area visible through an open door.

5. New Lakefront Luxury Cottage w/ Hot Tub

Mount Uniacke

includes taxes & fees

1 Nov - 2 Nov

A cabin with a deck, two red Adirondack chairs, and a fire pit.

6. Cozy Loft Bunkie | Sleeps 4 | BBQ + Fire Pit

Mount Uniacke

Jeannette

includes taxes & fees

1 Nov - 2 Nov

A cabin with a porch, outdoor seating, and string lights.

7. Pet-Friendly Cabin | Sleeps 2 | Private Fire Pit

Mount Uniacke

Charie

includes taxes & fees

1 Nov - 2 Nov

A room with a large window overlooking a lake, wicker furniture, and a view of trees and a dock.

8. Elite Lakehouse w/ Hot Tub & Sauna

Mount Uniacke

includes taxes & fees

1 Nov - 2 Nov

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Top Windsor Hotel Reviews

Slumber Inn

10/10 Excellent

"Staff were very sweet - room was clean and had a great breakfast. Would be nice to see rooms with two double beds"

Farmhouse Inn B&B

8/10 Good

"Our host was very hospitable and accommodating to our needs and requests. The room was a little chilly when we arrived but that was quickly and efficiently addressed by the provision of a space heater. Wifi was strong. The three course served breakfast was tasty and provided a good start to our day. The only drawback to the location was the noise when there was traffic on the road. It was quiet at night for sleeping but noticeable once vehicles were travelling on the road in front of the establishment. It is a good location for accessing Cape Split to explore the area."

Beautiful Oceanfront Home on the Minas Basin

10/10 Excellent

"Wow!!!!We have just spent the most WONDERFUL 3 nights in Cheverie, Nova Scotia at the All Tides Inn. From the moment we parked and instantly checked out the view we knew that we had chosen the right property for our shore vacation. Spotlessly clean, well and thoughtfully stocked immenities, comfortable and the best location.... we cannot possibly recommend this rental more! Excellent for a couple, 2 couples, a family with or without pets - it's just simply perfect! There is a list of touristy options, restaurants, wineries to keep you as busy (or not) as you want. All Tides Inn is just absolutely FANTASTIC!! Love it"

Pet-Friendly Cabin | Sleeps 2 | Private Fire Pit

10/10 Excellent

"We stayed the weekend at the bunkies. It was great! The bunkies are so cute! They are so clean and everything you need for a peaceful time. The bathrooms are so nice and clean. We used the hot tub and we had a nice fire. I certainly would recommend this place. The hosts Danny and Charmane are wonderful, very friendly. We will be back!"

Gateway to Annapolis Valley | Windsor Studio Suite

10/10 Excellent

"Well appointed and equipped with everything we needed. Cafes and bars in walking distance and supermarkets short drive. Parking convenient behind the property. Excellent communication from Dan on all aspects. Would definitely recommend for anyone exploring the area."

Family Bunkie | Sleeps 4 | Forest Views + Loft

10/10 Excellent

"Made our summer vacation perfect! My boyfriend doesn’t really care for cabins he prefers tent camping but said he wants to come back here and I agree it was a relaxing place, so quiet and cozy I was sad to go back home. The host was so nice and welcoming. All I can say is thank you so much I’m so excited to come back I loved my time at bunkie land!"

Romantic Nature Stay | Accessible Cabin for 2

10/10 Excellent

"Parfait. Danny et Charmen sont des gens serviables et aidant. Tout roule super bien. Mon conjoint est en fauteuil roulant et nous pouvons dire que la cabane et les salles de bain etsient vraiment accessibles. Un gros bravo! De tres beaux efforts. Endroit paisible et si beau. Nous reviendrons!!"

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, apart-hotels, 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 £96 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.

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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?

2 bedroom residential home in Kentville: This holiday home rental outside of Windsor is located by the ocean, and offers a private garden, WiFi and a Smart TV to help you feel perfectly comfortable in your new surroundings.

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 Trecothic Creek and Windsor Railway 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.

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Our top choices for Windsor holiday rentals

1. Gateway to Annapolis Valley | Windsor Studio Suite

2. Stylish Windsor Suite Near Wineries & Fundy Coast

3. Micro Boutique Living Wolfville

4. Good place to call home for a week or so

5. New Lakefront Luxury Cottage w/ Hot Tub

6. Cozy Loft Bunkie | Sleeps 4 | BBQ + Fire Pit

7. Pet-Friendly Cabin | Sleeps 2 | Private Fire Pit

8. Elite Lakehouse w/ Hot Tub & Sauna

9. Lakeside Cottage Retreat-Your Year Round Getaway

10. Family Bunkie | Sleeps 4 | Forest Views + Loft

11. Romantic Nature Stay | Accessible Cabin for 2

12. In the Heart of Town - Private Ground Level Unit

13. Studio-like Comfort in Wolfville’s Beating Heart

14. In Town - Summer St. Private Suite

15. Alligator Suite - downtown Wolfville

16. Suite 202- Two Bedroom apartment-style Suite w Balcony in Hybrid Hotel Wolfville

17. Downtown Wolfville Wine Country | 3rd Floor View 2BR & 3 Queen Beds

18. Suite 304- Two Bedroom apartment-style Suite w Balcony in Hybrid Hotel Wolfville

19. Suite 303 - Two Bedroom apartment-style Suite in Hybrid Hotel Wolfville

20. Wolfville at your Doorstep

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Top Windsor Hotel Reviews

Slumber Inn

Find out more about Windsor

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