A welcome sign at Cradle of Hockey, Long Pond, Windsor, Nova Scotia.

Windsor Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Windsor holiday rentals

1. Gateway to Annapolis Valley | Windsor Studio Suite

Gateway to Annapolis Valley | Windsor Studio Suite
Windsor
9.4 out of 10, Exceptional, (3 reviews)
"Great location"
United States
Heather H.
The price is AU$241
includes taxes & fees
16 Aug - 17 Aug
Gateway to Annapolis Valley | Windsor Studio Suite

2. Stylish Windsor Suite Near Wineries & Fundy Coast

Stylish Windsor Suite Near Wineries & Fundy Coast
Windsor
The price is AU$324
includes taxes & fees
19 Aug - 20 Aug
Stylish Windsor Suite Near Wineries & Fundy Coast

3. Micro Boutique Living Wolfville

Micro Boutique Living Wolfville
3.5 star property
Wolfville
9.0 out of 10, Wonderful, (1,221 reviews)
"Great stay."
Canada
Kimberly
The price is AU$187
includes taxes & fees
16 Aug - 17 Aug
Micro Boutique Living Wolfville

4. In Town and Close to Acadia - Apt.# 3 Ground Level

In Town and Close to Acadia - Apt.# 3 Ground Level
Wolfville
9.6 out of 10, Exceptional, (7 reviews)
"Check in and check out were very easy. The location was great. And the apartment was clean and well-maintained. "
United States
Ashley L.
The price is AU$599
includes taxes & fees
31 Aug - 1 Sept
In Town and Close to Acadia - Apt.# 3 Ground Level

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

Studio-like Comfort in Wolfville’s Beating Heart
Wolfville
9.8 out of 10, Exceptional, (44 reviews)
"Center of Wolfville, a short walk to shops on Main St. Clean and comfortable."
Canada
David
The price is AU$295
includes taxes & fees
9 Aug - 10 Aug
Studio-like Comfort in Wolfville’s Beating Heart

6. Suite 203 - 470 Main

Suite 203 - 470 Main
Wolfville
10.0 out of 10, Exceptional, (8 reviews)
"Perfect downtown spot, wish we had longer!"
United States
Kirby D.
The price is AU$643
includes taxes & fees
20 Aug - 21 Aug
Suite 203 - 470 Main

7. 4 Wolfville's DT Core | Two Queen Bds+ Sofa Bed

4 Wolfville's DT Core | Two Queen Bds+ Sofa Bed
Wolfville
9.4 out of 10, Exceptional, (26 reviews)
"Excellent location with everything right at your front door. The apartment was even better than expected; very spacious and beautifully decorated. Host was very communicative and responsive. Parking and checkin were a breeze."
Canada
Danielle
The price is AU$451
includes taxes & fees
3 Aug - 4 Aug
4 Wolfville's DT Core | Two Queen Bds+ Sofa Bed

8. Alligator Suite - downtown Wolfville

Alligator Suite - downtown Wolfville
Wolfville
9.2 out of 10, Wonderful, (7 reviews)
"Loved it Great location! Sweet place Parking worked out just fine Was surprised at first but turned out great"
Canada
Anna
The price is AU$281
includes taxes & fees
17 Aug - 18 Aug
Alligator Suite - downtown Wolfville

9. Upper Unit 1067 Rawding

Upper Unit 1067 Rawding
Port Williams
9.6 out of 10, Exceptional, (16 reviews)
"Very comfy beds & bedding. Relaxing stay so would highly recommend. "
United Kingdom
Janette M.
The price is AU$503
includes taxes & fees
3 Aug - 4 Aug
Upper Unit 1067 Rawding

10. In Town - Summer St. Private Suite

In Town - Summer St. Private Suite
Wolfville
8.6 out of 10, Excellent, (7 reviews)
"Clean, good location "
Canada
Patrick
The price is AU$305
includes taxes & fees
13 Aug - 14 Aug
In Town - Summer St. Private Suite

11. Suite 202 - 470 Main

Suite 202 - 470 Main
Wolfville
10.0 out of 10, Exceptional, (5 reviews)
"Great location "
United States
Julie N.
Suite 202 - 470 Main

12. Suite 304 - 470 Main

Suite 304 - 470 Main
Wolfville
10.0 out of 10, Exceptional, (6 reviews)
"Excellent place, handy to everything. Would definitely stay again"
Canada
lynn c.
The price is AU$657
includes taxes & fees
14 Aug - 15 Aug
Suite 304 - 470 Main

13. Gaspereau Suite -Jacuzzi, KngBd, DT

Gaspereau Suite -Jacuzzi, KngBd, DT
Wolfville
8.4 out of 10, Very good, (17 reviews)
"Yes!Everything was perfect "
United States
Elizabeth W.
The price is AU$359
includes taxes & fees
5 Aug - 6 Aug
Gaspereau Suite -Jacuzzi, KngBd, DT

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

Cozy Loft Bunkie | Sleeps 4 | BBQ + Fire Pit
Mount Uniacke
10.0 out of 10, Exceptional, (5 reviews)
"A beautiful property! The owners are very kind and helpful. A perfect getaway location, so peaceful and clean! "
Canada
Jeannette
The price is AU$208
includes taxes & fees
1 Sept - 2 Sept
Cozy Loft Bunkie | Sleeps 4 | BBQ + Fire Pit

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

In the Heart of Town - Private Ground Level Unit
Wolfville
9.0 out of 10, Wonderful, (35 reviews)
"Great parking, awesome home. Great stay."
United States
Cathy C.
The price is AU$324
includes taxes & fees
23 Aug - 24 Aug
In the Heart of Town - Private Ground Level Unit

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

Family Bunkie | Sleeps 4 | Forest Views + Loft
Mount Uniacke
10.0 out of 10, Exceptional, (2 reviews)
"We enjoyed our worry free stay. The hosts were very Kind and helpful. It was very clean,cozy and comfortable!"
Canada
Melanie M.
The price is AU$213
includes taxes & fees
1 Sept - 2 Sept
Family Bunkie | Sleeps 4 | Forest Views + Loft

17. 5 Apt. # 5 at 10 Summer Street Suites - Very Close to Acadia and in Town

5 Apt. # 5 at 10 Summer Street Suites - Very Close to Acadia and in Town
Wolfville
9.8 out of 10, Exceptional, (6 reviews)
"Gréât location "
United States
Julie N.
The price is AU$376
includes taxes & fees
24 Aug - 25 Aug
5 Apt. # 5 at 10 Summer Street Suites - Very Close to Acadia and in Town

18. Gaspereau Heritage House - Annapolis Valley

Gaspereau Heritage House - Annapolis Valley
Wolfville
Gaspereau Heritage House - Annapolis Valley

19. Sunken Escapes Kenny's (Unit 5)

Sunken Escapes Kenny's (Unit 5)
Sunken Lake
10.0 out of 10, Exceptional, (5 reviews)
"Very peaceful and relaxed. Close to amenities"
Canada
Murray
The price is AU$386
includes taxes & fees
2 Sept - 3 Sept
Sunken Escapes Kenny's (Unit 5)

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

Downtown Wolfville Wine Country | 3rd Floor View 2BR & 3 Queen Beds
Wolfville
The price is AU$441
includes taxes & fees
3 Aug - 4 Aug
Downtown Wolfville Wine Country | 3rd Floor View 2BR & 3 Queen Beds
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.
Save an average of 15% on thousands of hotels when you're signed in

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$187 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?

CAIA Lakeside Retreat- Sunken Lake, NS: This holiday home rental outside of Windsor is located on a lake, and has a balcony, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

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 Mermaid Theatre of Nova Scotia and Trecothic Creek and Windsor Railway.

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.