Birthplace of hockey

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
26 Jun - 28 Jun
In two months
7 Aug - 9 Aug
In three months
4 Sept - 6 Sept
In four months
2 Oct - 4 Oct

Our top choices for Windsor holiday rentals

Property grounds

Cozy Loft Bunkie | Sleeps 4 | BBQ + Fire Pit

Cozy Loft Bunkie | Sleeps 4 | BBQ + Fire Pit
Mount Uniacke
10.0 out of 10, Exceptional, (4 reviews)
"Bunkies are super clean. Washrooms are easy to access! Definitely recommend!"
Canada
Samantha
The price is HK$647
HK$1,118 total
includes taxes & fees
15 Jun - 16 Jun
Cozy Loft Bunkie | Sleeps 4 | BBQ + Fire Pit
Terrace/patio

Pet-Friendly Cabin | Sleeps 2 | Private Fire Pit

Pet-Friendly Cabin | Sleeps 2 | Private Fire Pit
Mount Uniacke
10.0 out of 10, Exceptional, (1 review)
"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
Andree
The price is HK$582
HK$1,044 total
includes taxes & fees
16 Jun - 17 Jun
Pet-Friendly Cabin | Sleeps 2 | Private Fire Pit
Interior

Romantic Nature Stay | Accessible Cabin for 2

Romantic Nature Stay | Accessible Cabin for 2
Mount Uniacke
The price is HK$588
HK$1,050 total
includes taxes & fees
16 Jun - 17 Jun
Romantic Nature Stay | Accessible Cabin for 2
Exterior

Family Bunkie | Sleeps 4 | Forest Views + Loft

Family Bunkie | Sleeps 4 | Forest Views + Loft
Mount Uniacke
10.0 out of 10, Exceptional, (1 review)
"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$647
HK$1,118 total
includes taxes & fees
15 Jun - 16 Jun
Family Bunkie | Sleeps 4 | Forest Views + Loft
Fireplace, DVD player, books

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, (10 reviews)
"Great peaceful comfortable cabin. Family loved it. Host was very helpful and responsive. "
Canada
Rany I.
The price is HK$1,400
HK$2,554 total
includes taxes & fees
28 Jun - 29 Jun
Cozy, stylish, and surrounded by nature; Sojourn Hideaway is the perfect getaway
Exterior

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$892
HK$1,196 total
includes taxes & fees
15 Jun - 16 Jun
Flamingo Suite (Downtown Wolfville)
Water view

Micro Boutique Living Wolfville

Micro Boutique Living Wolfville
3.5 star property
Wolfville
9.0 out of 10, Wonderful, (1,135 reviews)
"Great place 3rd stay Will definitely be back next time!"
Canada
Robin
The price is HK$1,003
HK$1,143 total
includes taxes & fees
6 Jul - 7 Jul
Micro Boutique Living Wolfville
Terrace/patio

Cozy 2-Bed Apartment in Town

Cozy 2-Bed Apartment in Town
Wolfville
8.8 out of 10, Excellent, (5 reviews)
"Downtown. Good location"
Canada
Rena
The price is HK$611
HK$1,488 total
includes taxes & fees
15 Jun - 16 Jun
Cozy 2-Bed Apartment in Town
Property grounds

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
10.0 out of 10, Exceptional, (5 reviews)
"Gréât location "
United States
Julie N.
The price is HK$857
HK$1,814 total
includes taxes & fees
15 Jun - 16 Jun
5 Apt. # 5 at 10 Summer Street Suites - Very Close to Acadia and in Town
Shower, hair dryer, towels, soap

Studio-like Comfort in Wolfville’s Beating Heart

Studio-like Comfort in Wolfville’s Beating Heart
Wolfville
9.8 out of 10, Exceptional, (38 reviews)
"Great location, clean, responsive host. Will stay again! "
Canada
stacey h.
The price is HK$863
HK$1,737 total
includes taxes & fees
1 Jul - 2 Jul
Studio-like Comfort in Wolfville’s Beating Heart
Property grounds

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, (23 reviews)
"We really enjoyed our stay here. The apartment was clean and spacious and we really loved the mix of new and old in the decor. It's a very pretty space with a lot of light. It's just a few steps from a trendy little street full of shops and restaurants. And just a couple blocks from the Saturday farmers market. It was a perfect home base for exploring the Annapolis valley."
Canada
Bobbie-Joe
The price is HK$1,094
HK$2,486 total
includes taxes & fees
6 Jul - 7 Jul
4 Wolfville's DT Core | Two Queen Bds+ Sofa Bed
Property grounds

Wolfville at your Doorstep

Wolfville at your Doorstep
Wolfville
9.6 out of 10, Exceptional, (30 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$585
HK$1,459 total
includes taxes & fees
18 Jun - 19 Jun
Wolfville at your Doorstep
Property grounds

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, (33 reviews)
"Great location "
Canada
Megan
The price is HK$1,023
HK$2,029 total
includes taxes & fees
26 Jun - 27 Jun
In the Heart of Town - Private Ground Level Unit
Fridge, microwave, oven, stovetop

Suite 202 - 470 Main

Suite 202 - 470 Main
Wolfville
10.0 out of 10, Exceptional, (4 reviews)
"Great location "
United States
Julie N.
The price is HK$1,344
HK$2,212 total
includes taxes & fees
16 Jun - 17 Jun
Suite 202 - 470 Main
Fridge, microwave, oven, stovetop

Suite 201 - 470 Main

Suite 201 - 470 Main
Wolfville
10.0 out of 10, Exceptional, (1 review)
"Enjoyed my stay."
United States
Harry G.
The price is HK$1,456
HK$2,277 total
includes taxes & fees
5 Jul - 6 Jul
Suite 201 - 470 Main
Fridge, microwave, oven, stovetop

Suite 203 - 470 Main

Suite 203 - 470 Main
Wolfville
10.0 out of 10, Exceptional, (8 reviews)
"We thoroughly enjoyed our stay. Our unit was well equipped, very clean and very comfortable. Highly recommend !! "
Canada
Valerie
The price is HK$1,445
HK$2,340 total
includes taxes & fees
16 Jun - 17 Jun
Suite 203 - 470 Main
Terrace/patio

Gaspereau Suite -Jacuzzi, KngBd, DT

Gaspereau Suite -Jacuzzi, KngBd, DT
Wolfville
8.2 out of 10, Very good, (16 reviews)
"Yes!Everything was perfect "
United States
Elizabeth W.
The price is HK$1,506
HK$1,954 total
includes taxes & fees
25 Jun - 26 Jun
Gaspereau Suite -Jacuzzi, KngBd, DT
Terrace/patio

Sunken Escapes Kenny's (Unit 5)

Sunken Escapes Kenny's (Unit 5)
Sunken Lake
10.0 out of 10, Exceptional, (5 reviews)
"Loved the sound of the loons on the lake, cozy accommodations and the beautiful scenery. Nice place, 10/10 "
Canada
Constance
The price is HK$741
HK$1,696 total
includes taxes & fees
16 Jun - 17 Jun
Sunken Escapes Kenny's (Unit 5)
Interior

Sunken Escapes #3 Kit's Retreat

Sunken Escapes #3 Kit's Retreat
Kings County
8.0 out of 10, Very good, (2 reviews)
"We came for the marathon and brought our granddaughter. The property exceeded expectations; it was clean comfortable and a joy to stay in. We had a great time and will definitely be back again if we stay in the area."
Canada
Jason T.
The price is HK$970
HK$2,014 total
includes taxes & fees
17 Jun - 18 Jun
Sunken Escapes #3 Kit's Retreat
Terrace/patio

Leland’s Lakehouse

Leland’s Lakehouse
Kings County
9.0 out of 10, Wonderful, (6 reviews)
"The cabin is in a fantastic location looking over the lake, the interior was very clean and looks great. Convinent location for getting to vineyards and wolfvile. I would highly recommend this place for anyone to stay at. "
Canada
Max D.
The price is HK$1,059
HK$2,495 total
includes taxes & fees
15 Jun - 16 Jun
Leland’s Lakehouse
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

Old Orchard Inn

Old Orchard Inn

6/10 Okay
"Potato chip on floor when we arrived, hand held shower head not working, no place to hang towels, tv not working for half our stay and response from front desk after three calls was that a work order had been submitted.. in positive side food was very good, wait staff (Mateo) very friendly and attentive and property very attractive."
Ronald 2-night trip
Posted 3 hours ago
Old Orchard 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
  • 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?

Leland’s Lakehouse: This holiday home rental outside of Windsor offers a fireplace, a balcony and a BBQ to help you feel perfectly comfortable 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 Shand House Museum 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.