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

Windsor Holiday Rentals

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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 NZ$257
includes taxes & fees
19 Aug - 20 Aug
Gateway to Annapolis Valley | Windsor Studio Suite

2. Stylish Windsor Suite Near Wineries & Fundy Coast

Stylish Windsor Suite Near Wineries & Fundy Coast
Windsor
10.0 out of 10, Exceptional, (1 review)
"The accommodation was impeccably clean and well appointed with everything a traveller would require. Lots of coffee, close distance to amenities, shops, restaurants and more. I would certainly return and hopefully, stay longer !"
Canada
Karen
The price is NZ$311
includes taxes & fees
19 Aug - 20 Aug
Stylish Windsor Suite Near Wineries & Fundy Coast

3. Sakura Valley Studio Suite #4 / Private Entrance in beautiful Annapolis Valley

Sakura Valley Studio Suite #4 / Private Entrance in beautiful Annapolis Valley
North Alton
The price is NZ$189
includes taxes & fees
12 Aug - 13 Aug
Sakura Valley Studio Suite #4 / Private Entrance in beautiful Annapolis Valley

4. Sakura Valley Studio Suite #9 / Private Entrance in beautiful Annapolis Valley

Sakura Valley Studio Suite #9 / Private Entrance in beautiful Annapolis Valley
North Alton
The price is NZ$201
includes taxes & fees
13 Aug - 14 Aug
Sakura Valley Studio Suite #9 / Private Entrance in beautiful Annapolis Valley

5. Sakura Valley Studio Suite #3 / Private Entrance in beautiful Annapolis Valley

Sakura Valley Studio Suite #3 / Private Entrance in beautiful Annapolis Valley
North Alton
10.0 out of 10, Exceptional, (2 reviews)
"So glad we chose to stay at Sakura Valley! Highly recommend! The host is lovely and accommodating, the suite was very clean, beds comfortable. Location is great! It feels secluded but is close to the highway. I would definitely stay again."
Canada
Nadia
The price is NZ$195
includes taxes & fees
23 Aug - 24 Aug
Sakura Valley Studio Suite #3 / Private Entrance in beautiful Annapolis Valley

6. Sakura Valley Studio Suite #1 / Private Entrance in beautiful Annapolis Valley

Sakura Valley Studio Suite #1 / Private Entrance in beautiful Annapolis Valley
North Alton
10.0 out of 10, Exceptional, (3 reviews)
"really great spot. clean. just what you need. complimentary snacks which i pprecited. would definitely stay again."
Canada
Bianca
The price is NZ$235
includes taxes & fees
12 Aug - 13 Aug
Sakura Valley Studio Suite #1 / Private Entrance in beautiful Annapolis Valley

7. Sakura Valley Studio Suite #2 / Private Entrance in beautiful Annapolis Valley

Sakura Valley Studio Suite #2 / Private Entrance in beautiful Annapolis Valley
North Alton
10.0 out of 10, Exceptional, (1 review)
"👍"
Canada
Christopher
The price is NZ$180
includes taxes & fees
19 Aug - 20 Aug
Sakura Valley Studio Suite #2 / Private Entrance in beautiful Annapolis Valley

8. 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 NZ$243
includes taxes & fees
1 Sept - 2 Sept
Cozy Loft Bunkie | Sleeps 4 | BBQ + Fire Pit

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

Pet-Friendly Cabin | Sleeps 2 | Private Fire Pit
Mount Uniacke
10.0 out of 10, Exceptional, (2 reviews)
"They were excellent for couples and families. Great hosts and wonderful facilities. The couple that own it are very sweet and kind. I have nothing negative to say, I just wanna go back to paradise!"
Canada
Anonymous traveller
The price is NZ$243
includes taxes & fees
1 Sept - 2 Sept
Pet-Friendly Cabin | Sleeps 2 | Private Fire Pit

10. Micro Boutique Living Wolfville

Micro Boutique Living Wolfville
3.5 star property
Wolfville
9.0 out of 10, Wonderful, (1,244 reviews)
"Great stay."
Canada
Kimberly
The price is NZ$224
includes taxes & fees
16 Aug - 17 Aug
Micro Boutique Living Wolfville

11. Romantic Nature Stay | Accessible Cabin for 2

Romantic Nature Stay | Accessible Cabin for 2
Mount Uniacke
10.0 out of 10, Exceptional, (2 reviews)
"That looked like a part of heaven to us. Every thing was more than our expectations. At the top of a mountainous region, quiet and peaceful, with great amenities and hosts. Danny and Cherman did their best to provide what is needed for an exciting stay. Happy of this unique experience."
Canada
Morteza
The price is NZ$232
includes taxes & fees
8 Sept - 9 Sept
Romantic Nature Stay | Accessible Cabin for 2

12. 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 NZ$256
includes taxes & fees
8 Sept - 9 Sept
Family Bunkie | Sleeps 4 | Forest Views + Loft

13. Cozy, stylish, and surrounded by nature; Sojourn Hideaway is the perfect getaway

Cozy, stylish, and surrounded by nature; Sojourn Hideaway is the perfect getaway
Windsor
9.8 out of 10, Exceptional, (14 reviews)
"Great place to stay if you want a nice quiet retreat. Very clean and cozy. Great kitchen and we loved the woodstove amd record player. "
Canada
Steffen R.
The price is NZ$462
includes taxes & fees
3 Sept - 4 Sept
Cozy, stylish, and surrounded by nature; Sojourn Hideaway is the perfect getaway

14. 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 NZ$362
includes taxes & fees
27 Aug - 28 Aug
In Town - Summer St. Private Suite

15. Lakeside Cottage Retreat-Your Year Round Getaway

Lakeside Cottage Retreat-Your Year Round Getaway
Windsor
10.0 out of 10, Exceptional, (2 reviews)
"Great cottage on the lake. Canoe and paddle boat provided for your leisure. Great for families or a quiet getaway. Will be staying at this property again."
United States
Alane B.
The price is NZ$556
includes taxes & fees
1 Sept - 2 Sept
Lakeside Cottage Retreat-Your Year Round Getaway

16. 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 NZ$344
includes taxes & fees
9 Sept - 10 Sept
Studio-like Comfort in Wolfville’s Beating Heart

17. Sunken Escapes Kenny's (Unit 5)

Sunken Escapes Kenny's (Unit 5)
Sunken Lake
10.0 out of 10, Exceptional, (6 reviews)
"Very peaceful and relaxed. Close to amenities"
Canada
Murray
The price is NZ$478
includes taxes & fees
9 Sept - 10 Sept
Sunken Escapes Kenny's (Unit 5)

18. Lower Unit 1067 Rawding

Lower Unit 1067 Rawding
Port Williams
10.0 out of 10, Exceptional, (5 reviews)
"The neiborhood was very quiet. It was a peaceful and relaxing stay. The home was very nice and met our needs."
United States
Stacy H.
The price is NZ$474
includes taxes & fees
24 Aug - 25 Aug
Lower Unit 1067 Rawding

19. 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 NZ$376
includes taxes & fees
27 Aug - 28 Aug
In the Heart of Town - Private Ground Level Unit

20. Wolfville at your Doorstep

Wolfville at your Doorstep
Wolfville
9.6 out of 10, Exceptional, (31 reviews)
"The location was great, within walking distance of restaurants and downtown. Any communication with the owners had quick responses. Parking was provided and convenient. I would recommend this property and would stay again without hesitation."
Canada
SHELLEY
The price is NZ$386
includes taxes & fees
25 Aug - 26 Aug
Wolfville at your Doorstep
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$224 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

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?

Beautiful Oceanfront Home on the Minas Basin: This holiday home rental outside of Windsor is located by the ocean, and has a fireplace, a balcony and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You can relax into your holiday with a garden and a selection of games.

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.