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
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Windsor holiday rentals

Living area

1. Stylish Windsor Suite Near Wineries & Fundy Coast

Stylish Windsor Suite Near Wineries & Fundy Coast
Windsor
9.6 out of 10, Exceptional, (4 reviews)
"The place was very clean and well kept. Check in was super easy and Dan is very good with all the instructions and communication. Will come back for sure."
Canada
Lucie
The price is HK$813
HK$1,261 total
includes taxes & fees
29 Sept - 30 Sept
Stylish Windsor Suite Near Wineries & Fundy Coast
Room

2. Gateway to Annapolis Valley | Windsor Studio Suite

Gateway to Annapolis Valley | Windsor Studio Suite
Windsor
9.8 out of 10, Exceptional, (7 reviews)
"Comfortable, remodeled apartment with full kitchen and all necessary amenities. Host Dan, was very communicative and made the stay a breeze. Convenient location to the local vineyards"
United States
Michael
The price is HK$818
HK$1,267 total
includes taxes & fees
29 Sept - 30 Sept
Gateway to Annapolis Valley | Windsor Studio Suite
Room

3. Sunken Escapes ZEEK (Unit 6)

Sunken Escapes ZEEK (Unit 6)
Sunken Lake
9.0 out of 10, Wonderful, (2 reviews)
"Was difficult to access check in website as there is no service at the site…eventually got enough bars to get the code for the door! Super cute cottage, very clean. Lovely site. Would definitely visit again."
Canada
Angela
The price is HK$847
HK$1,664 total
includes taxes & fees
12 Oct - 13 Oct
Sunken Escapes ZEEK (Unit 6)
Interior

4. Romantic Nature Stay | Accessible Cabin for 2

Romantic Nature Stay | Accessible Cabin for 2
Mount Uniacke
10.0 out of 10, Exceptional, (3 reviews)
"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!!"
Canada
Edith
The price is HK$593
HK$1,058 total
includes taxes & fees
5 Oct - 6 Oct
Romantic Nature Stay | Accessible Cabin for 2
Property grounds

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

Cozy Loft Bunkie | Sleeps 4 | BBQ + Fire Pit
Mount Uniacke
10.0 out of 10, Exceptional, (6 reviews)
"A beautiful property! The owners are very kind and helpful. A perfect getaway location, so peaceful and clean! "
Canada
Jeannette
The price is HK$652
HK$1,126 total
includes taxes & fees
6 Oct - 7 Oct
Cozy Loft Bunkie | Sleeps 4 | BBQ + Fire Pit
Terrace/patio

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

Sakura Valley Studio Suite #4 / Private Entrance in beautiful Annapolis Valley
North Alton
10.0 out of 10, Exceptional, (2 reviews)
"Nice, new and clean place."
Canada
Donald
The price is HK$610
HK$1,004 total
includes taxes & fees
16 Sept - 17 Sept
Sakura Valley Studio Suite #4 / Private Entrance in beautiful Annapolis Valley
Property grounds

7. In Town - Summer St. Private Suite

In Town - Summer St. Private Suite
Wolfville
9.2 out of 10, Wonderful, (11 reviews)
"Clean, good location "
Canada
Patrick
The price is HK$833
HK$1,715 total
includes taxes & fees
22 Sept - 23 Sept
In Town - Summer St. Private Suite
Exterior

8. Flamingo Suite (Downtown Wolfville)

Flamingo Suite (Downtown Wolfville)
Wolfville
8.8 out of 10, Excellent, (5 reviews)
"We had an excellent stay. The room was clean, the host was responsive, and the location was ideal for visiting the downtown."
Canada
Barbara D.
The price is HK$1,137
HK$1,483 total
includes taxes & fees
4 Oct - 5 Oct
Flamingo Suite (Downtown Wolfville)
Room

9. 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 HK$752
HK$1,605 total
includes taxes & fees
28 Sept - 29 Sept
Studio-like Comfort in Wolfville’s Beating Heart
Property grounds

10. Bespoke Lake Cottage

Bespoke Lake Cottage
Kings County
9.4 out of 10, Exceptional, (10 reviews)
"We have a lovely stay - our only complaint is that we didn't book for long enough! The cottage is very charming and very clean. Bed is comfortable and kitchen had all equipment needed for food prep. "
Canada
Lily S.
The price is HK$770
HK$2,077 total
includes taxes & fees
4 Oct - 5 Oct
Bespoke Lake Cottage
Property grounds

11. 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, (36 reviews)
"Great parking, awesome home. Great stay."
United States
Cathy C.
The price is HK$833
HK$1,786 total
includes taxes & fees
30 Sept - 1 Oct
In the Heart of Town - Private Ground Level Unit
Property grounds

12. 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 HK$833
HK$1,786 total
includes taxes & fees
7 Oct - 8 Oct
Wolfville at your Doorstep
Terrace/patio

13. Leland’s Lakehouse

Leland’s Lakehouse
Kings County
9.4 out of 10, Exceptional, (8 reviews)
"Private and quiet Cozy and cute Place was well maintained Easy to find Very clean Super close to the lake Wonderful hot tub"
Canada
Nicole C.
The price is HK$1,067
HK$2,404 total
includes taxes & fees
6 Oct - 7 Oct
Leland’s Lakehouse
Exterior

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

Family Bunkie | Sleeps 4 | Forest Views + Loft
Mount Uniacke
10.0 out of 10, Exceptional, (3 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 HK$652
HK$1,126 total
includes taxes & fees
5 Oct - 6 Oct
Family Bunkie | Sleeps 4 | Forest Views + Loft
Interior

15. Archie's Lakeside Cabin

Archie's Lakeside Cabin
Kings County
7.4 out of 10, Good, (9 reviews)
"Great stay!"
Canada
Ashwin K.
The price is HK$741
HK$2,068 total
includes taxes & fees
22 Sept - 23 Sept
Archie's Lakeside Cabin
Property grounds

16. CAIA Lakeside Retreat- Sunken Lake, NS

CAIA Lakeside Retreat- Sunken Lake, NS
Sunken Lake
9.4 out of 10, Exceptional, (16 reviews)
"Pet friendly"
Canada
Lori
The price is HK$830
HK$2,149 total
includes taxes & fees
7 Oct - 8 Oct
CAIA Lakeside Retreat- Sunken Lake, NS
Terrace/patio

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

Pet-Friendly Cabin | Sleeps 2 | Private Fire Pit
Mount Uniacke
9.6 out of 10, Exceptional, (5 reviews)
"Gorgeous location, friendly and supportive hosts, clean room with everything possible in it. Pet friendly. Wonderful hot tub with great view."
United States
Charie
The price is HK$587
HK$1,052 total
includes taxes & fees
6 Oct - 7 Oct
Pet-Friendly Cabin | Sleeps 2 | Private Fire Pit
Exterior

18. 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 HK$519
HK$901 total
includes taxes & fees
22 Sept - 23 Sept
Sakura Valley Studio Suite #2 / Private Entrance in beautiful Annapolis Valley
Room

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

Sakura Valley Studio Suite #9 / Private Entrance in beautiful Annapolis Valley
North Alton
10.0 out of 10, Exceptional, (1 review)
"Logement équipé et propre. Acces facile! Je recommande."
France
Justine
The price is HK$686
HK$1,058 total
includes taxes & fees
16 Sept - 17 Sept
Sakura Valley Studio Suite #9 / Private Entrance in beautiful Annapolis Valley
Property grounds

20. 6 Charming Private 1-Bedroom Apartment in the Heart of Wolfville

6 Charming Private 1-Bedroom Apartment in the Heart of Wolfville
Wolfville
8.6 out of 10, Excellent, (7 reviews)
"It’s a noisy house so pack earplugs Host was great and accommodating when we needed supplies. "
Canada
Julie N.
The price is HK$931
HK$1,911 total
includes taxes & fees
16 Sept - 17 Sept
6 Charming Private 1-Bedroom Apartment in the Heart of Wolfville
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.
View all properties
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

Super 8 by Wyndham Windsor NS

Super 8 by Wyndham Windsor NS

10/10 Excellent
"Very clean, quiet , great location breakfast was very simple coffee, bagels,cereal and pancakes"
lori 1-night trip
Posted less than an hour ago
Super 8 by Wyndham Windsor NS

Find out more about Windsor

Search for holiday rentals in Windsor on Expedia! You can easily find your home rentals, villas, holiday apartments in Windsor using one of the methods below:

  • View our selection of featured holiday rentals in Windsor
  • Use the map to find apartments and other holiday homes in the Windsor neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Windsor while they last

Look no further and take a look at our great range of rental properties in Windsor!

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.