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

Windsor Holiday Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

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

Gateway to Annapolis Valley | Windsor Studio Suite
Windsor
9.8 out of 10, Exceptional, (8 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$814
HK$1,326 total
includes taxes & fees
28 Sept - 29 Sept
Gateway to Annapolis Valley | Windsor Studio Suite
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

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$699
HK$1,195 total
includes taxes & fees
5 Oct - 6 Oct
Stylish Windsor Suite Near Wineries & Fundy Coast
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

Micro Boutique Living Wolfville
3.5 star property
Wolfville
9.0 out of 10, Wonderful, (1,330 reviews)
"Location is perfect"
Canada
Kelly
The price is HK$1,048
HK$1,195 total
includes taxes & fees
18 Oct - 19 Oct
Micro Boutique Living Wolfville
A cabin with a deck, two red Adirondack chairs, and a fire pit.

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

Cozy Loft Bunkie | Sleeps 4 | BBQ + Fire Pit
Mount Uniacke
10.0 out of 10, Exceptional, (7 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$641
HK$1,107 total
includes taxes & fees
4 Oct - 5 Oct
Cozy Loft Bunkie | Sleeps 4 | BBQ + Fire Pit
A wooden cabin with a balcony, surrounded by trees and snow.

5. 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$641
HK$1,107 total
includes taxes & fees
18 Oct - 19 Oct
Family Bunkie | Sleeps 4 | Forest Views + Loft
A double-decker bus in a vineyard with a red telephone booth.

6. 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, (30 reviews)
"Great location. Very clean."
Canada
Sarah
The price is HK$1,088
HK$2,335 total
includes taxes & fees
19 Oct - 20 Oct
4 Wolfville's DT Core | Two Queen Bds+ Sofa Bed
A two-story house with a balcony, a patio with chairs and potted plants, and a large window.

7. Gaspereau Suite -Jacuzzi, KngBd, DT

Gaspereau Suite -Jacuzzi, KngBd, DT
Wolfville
8.4 out of 10, Very good, (18 reviews)
"Such a quaint central location. We loved sitting outdoors and enjoying the tranquility and peaceful surroundings within walking distance of downtown Wolfville. We highly recommend this location. Beautiful and tranquil."
Canada
William
The price is HK$1,432
HK$1,809 total
includes taxes & fees
11 Oct - 12 Oct
Gaspereau Suite -Jacuzzi, KngBd, DT
A lakeside view with trees, a dock, and a grassy area.

8. Lakeside Cottage Retreat-Your Year Round Getaway

Lakeside Cottage Retreat-Your Year Round Getaway
Windsor
9.4 out of 10, Exceptional, (3 reviews)
"The cottage is located on a beautiful lake. It was great for our short stay."
Canada
Kathryn
The price is HK$1,722
HK$2,140 total
includes taxes & fees
30 Sept - 1 Oct
Lakeside Cottage Retreat-Your Year Round Getaway
A hallway with a bench, a rug, and a door leading to another room.

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

Downtown Wolfville Wine Country | 3rd Floor View 2BR & 3 Queen Beds
Wolfville
9.0 out of 10, Wonderful, (2 reviews)
"It was a great stay in a great location!"
United States
Craig M.
The price is HK$1,331
HK$2,656 total
includes taxes & fees
4 Oct - 5 Oct
Downtown Wolfville Wine Country | 3rd Floor View 2BR & 3 Queen Beds
A double-decker bus in a vineyard with a red telephone booth.

10. 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, (8 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 HK$1,409
HK$2,751 total
includes taxes & fees
28 Sept - 29 Sept
In Town and Close to Acadia - Apt.# 3 Ground Level
A modern kitchen with a central island, pendant lighting, and stainless steel appliances.

11. Suite 204- Two Bedroom apartment-style Suite w Balcony in Hybrid Hotel Wolfville

Suite 204- Two Bedroom apartment-style Suite w Balcony in Hybrid Hotel Wolfville
Wolfville
10.0 out of 10, Exceptional, (4 reviews)
"Super clean. Easy to find, host had great communication"
United States
Nadia D.
The price is HK$1,276
HK$2,020 total
includes taxes & fees
28 Oct - 29 Oct
Suite 204- Two Bedroom apartment-style Suite w Balcony in Hybrid Hotel Wolfville
A double-decker bus in a vineyard with a red telephone booth.

12. 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, (37 reviews)
"Location is excellent right in the heart of Wolfville as youcan park your car and walk to a lot of places such as restaurants, winery and tourist information center (if you decide to do the Magic wine bus)"
United States
Susan S.
The price is HK$819
HK$1,711 total
includes taxes & fees
4 Oct - 5 Oct
In the Heart of Town - Private Ground Level Unit
A modern kitchen with a central island, stainless steel appliances, and pendant lighting.

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

Suite 202- Two Bedroom apartment-style Suite w Balcony in Hybrid Hotel Wolfville
Wolfville
10.0 out of 10, Exceptional, (6 reviews)
"Great location "
United States
Julie N.
The price is HK$1,331
HK$2,083 total
includes taxes & fees
26 Oct - 27 Oct
Suite 202- Two Bedroom apartment-style Suite w Balcony in Hybrid Hotel Wolfville
A modern kitchen with stainless steel appliances, wooden cabinets, and pendant lighting.

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

Suite 304- Two Bedroom apartment-style Suite w Balcony in Hybrid Hotel Wolfville
Wolfville
10.0 out of 10, Exceptional, (7 reviews)
"This was an amazing property for a short stay in Wolfville. It was comfortable and in the perfect spot to explore the local area. We will be definetly use this place again when we visit Wolfville next."
United States
Stuart C.
The price is HK$1,653
HK$2,450 total
includes taxes & fees
28 Sept - 29 Sept
Suite 304- Two Bedroom apartment-style Suite w Balcony in Hybrid Hotel Wolfville
A cabin with a wooden exterior, a balcony, and a grill area.

15. Sunken Escapes Kenny's (Unit 5)

Sunken Escapes Kenny's (Unit 5)
Sunken Lake
10.0 out of 10, Exceptional, (7 reviews)
"Very peaceful and relaxed. Close to amenities"
Canada
Murray
The price is HK$926
HK$1,876 total
includes taxes & fees
13 Oct - 14 Oct
Sunken Escapes Kenny's (Unit 5)
A two-story house with a porch, a wooden door, and a number '5' sign.

16. Cactus Suite (Downtown Wolfville)

Cactus Suite (Downtown Wolfville)
Wolfville
9.0 out of 10, Wonderful, (6 reviews)
"Very quaintly decorated loft. Walking distance to everything downtown and beyond and very nicely equipped. "
Canada
Darryl
The price is HK$1,161
HK$1,500 total
includes taxes & fees
1 Oct - 2 Oct
Cactus Suite (Downtown Wolfville)
A log cabin interior with a large window, a red door, and a gray sofa.

17. 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$582
HK$1,040 total
includes taxes & fees
18 Oct - 19 Oct
Romantic Nature Stay | Accessible Cabin for 2
A double-decker bus in a vineyard with a red telephone booth.

18. 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$910
HK$1,815 total
includes taxes & fees
28 Sept - 29 Sept
6 Charming Private 1-Bedroom Apartment in the Heart of Wolfville
A cabin with a porch, outdoor seating, and string lights.

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

Pet-Friendly Cabin | Sleeps 2 | Private Fire Pit
Mount Uniacke
9.8 out of 10, Exceptional, (7 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$577
HK$1,034 total
includes taxes & fees
18 Oct - 19 Oct
Pet-Friendly Cabin | Sleeps 2 | Private Fire Pit
A covered porch with a wooden deck, a black door, and a view of the street.

20. Cozy 2-Bed Apartment in Town

Cozy 2-Bed Apartment in Town
Wolfville
9.4 out of 10, Exceptional, (8 reviews)
"Great location"
Canada
Claude F.
The price is HK$1,059
HK$1,985 total
includes taxes & fees
30 Sept - 1 Oct
Cozy 2-Bed Apartment in Town
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

Slumber Inn

Slumber Inn

8/10 Good
"Lovely stay and great staff"
Mary 2-night trip
Posted 1 hour ago
Slumber Inn

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
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  • 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 Mermaid Theatre of Nova Scotia, 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 Fort Edward National Historic Site.

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.