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

Windsor Vacation Rentals

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Our top choices for Windsor vacation rentals

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 CA $143
CA $235 total
includes taxes & fees
Sep 28 - Sep 29
Gateway to Annapolis Valley | Windsor Studio Suite

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 CA $140
CA $231 total
includes taxes & fees
Oct 1 - Oct 2
Stylish Windsor Suite Near Wineries & Fundy Coast

3. 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 CA $116
CA $200 total
includes taxes & fees
Oct 14 - Oct 15
Cozy Loft Bunkie | Sleeps 4 | BBQ + Fire Pit

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

Pet-Friendly Cabin | Sleeps 2 | Private Fire Pit
Mount Uniacke
9.8 out of 10, Exceptional, (6 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 CA $104
CA $186 total
includes taxes & fees
Oct 14 - Oct 15
Pet-Friendly Cabin | Sleeps 2 | Private Fire Pit

5. 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 CA $137
CA $374 total
includes taxes & fees
Oct 4 - Oct 5
Bespoke Lake Cottage

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, (4 reviews)
"Nice, new and clean place."
Canada
Donald
The price is CA $117
CA $188 total
includes taxes & fees
Sep 20 - Sep 21
Sakura Valley Studio Suite #4 / Private Entrance in beautiful Annapolis Valley

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 CA $148
CA $302 total
includes taxes & fees
Sep 22 - Sep 23
In Town - Summer St. Private Suite

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 CA $209
CA $270 total
includes taxes & fees
Sep 22 - Sep 23
Alligator Suite - downtown Wolfville

9. 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 CA $139
CA $308 total
includes taxes & fees
Oct 12 - Oct 13
Sunken Escapes Kenny's (Unit 5)

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

Studio-like Comfort in Wolfville’s Beating Heart
Wolfville
9.8 out of 10, Exceptional, (45 reviews)
"Center of Wolfville, a short walk to shops on Main St. Clean and comfortable."
Canada
David
The price is CA $118
CA $263 total
includes taxes & fees
Sep 28 - Sep 29
Studio-like Comfort in Wolfville’s Beating Heart

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 CA $148
CA $314 total
includes taxes & fees
Oct 4 - Oct 5
In the Heart of Town - Private Ground Level Unit

12. 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 CA $164
CA $335 total
includes taxes & fees
Sep 28 - Sep 29
5 Apt. # 5 at 10 Summer Street Suites - Very Close to Acadia and in Town

13. 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 CA $131
CA $368 total
includes taxes & fees
Sep 21 - Sep 22
Archie's Lakeside Cabin

14. 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 CA $148
CA $297 total
includes taxes & fees
Oct 6 - Oct 7
Wolfville at your Doorstep

15. Suite 302- One Bedroom apartment-style Suite w Balcony in Hybrid Hotel Wolfville

Suite 302- One Bedroom apartment-style Suite w Balcony in Hybrid Hotel Wolfville
Wolfville
9.0 out of 10, Wonderful, (2 reviews)
"The Gaspereau suite was clean & beautiful! We loved that it was right downtown Wolfville. "
Canada
Brenda
The price is CA $268
CA $398 total
includes taxes & fees
Oct 13 - Oct 14
Suite 302- One Bedroom apartment-style Suite w Balcony in Hybrid Hotel Wolfville

16. 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 CA $196
CA $445 total
includes taxes & fees
Sep 27 - Sep 28
4 Wolfville's DT Core | Two Queen Bds+ Sofa Bed

17. Suite 201 - Spacious One Bedroom Apartment-Style Suite in Hybrid Hotel Wolfville

Suite 201 - Spacious One Bedroom Apartment-Style Suite in Hybrid Hotel Wolfville
Wolfville
10.0 out of 10, Exceptional, (3 reviews)
"Enjoyed my stay."
United States
Harry G.
The price is CA $288
CA $445 total
includes taxes & fees
Oct 8 - Oct 9
Suite 201 - Spacious One Bedroom Apartment-Style Suite in Hybrid Hotel Wolfville

18. 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 CA $258
CA $334 total
includes taxes & fees
Oct 11 - Oct 12
Gaspereau Suite -Jacuzzi, KngBd, DT

19. 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 CA $189
CA $442 total
includes taxes & fees
Oct 12 - Oct 13
Leland’s Lakehouse

20. 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 CA $147
CA $377 total
includes taxes & fees
Oct 12 - Oct 13
CAIA Lakeside Retreat- Sunken Lake, NS
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Windsor. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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Frequently asked questions

Are there vacation rentals in Windsor?

Yes, we give you a choice of vacation rentals in Windsor close to Windsor Hockey Heritage Centre, or you can choose a secluded option if you'd like a relaxing place to 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's the top vacation rental in Windsor?

2 bedroom residential home in Kentville: Visitors like this Windsor vacation home rental. It is located by the ocean and offers a private yard, 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 vacation rentals like in Windsor?

Vacation rentals are private properties you can stay in for several days or more in Windsor. Vacation rentals provide amenities such as patios, hot tubs, and fire pits so you'll have everything you want. If you're concerned about a sanitized environment, vacation rentals can provide a sense of privacy away from public hotel elevators and busy lobbies while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great choice for a small group gathering.