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, (12 reviews)
"Great location"
United States
Heather H.
The price is CA $134
CA $212 total
includes taxes & fees
Nov 5 - Nov 6
Gateway to Annapolis Valley | Windsor Studio Suite

2. Charming Windsor Suite | Walk to Shops & Dining

Charming Windsor Suite | Walk to Shops & Dining
Windsor
The price is CA $99
CA $178 total
includes taxes & fees
Dec 1 - Dec 2
Charming Windsor Suite | Walk to Shops & Dining

3. Stylish Windsor Suite Near Wineries & Fundy Coast

Stylish Windsor Suite Near Wineries & Fundy Coast
Windsor
9.8 out of 10, Exceptional, (7 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 $131
CA $208 total
includes taxes & fees
Nov 10 - Nov 11
Stylish Windsor Suite Near Wineries & Fundy Coast

4. Micro Boutique Living Wolfville

Micro Boutique Living Wolfville
3.5 star property
Wolfville
9.0 out of 10, Wonderful, (1,337 reviews)
"We had a wonderful stay in Wolfville! The room was comfortable, clean, and welcoming, and the location made it easy to explore the area. We really enjoyed our time here and appreciated the overall experience. We would happily stay here again and recommend it to anyone visiting Wolfville!"
Canada
Ernesto
The price is CA $189
CA $215 total
includes taxes & fees
Nov 11 - Nov 12
Micro Boutique Living Wolfville

5. StELLA – The Star Dome | Celestial Vineyard Escape

StELLA – The Star Dome | Celestial Vineyard Escape
Windsor
The price is CA $172
CA $304 total
includes taxes & fees
Nov 8 - Nov 9
StELLA – The Star Dome | Celestial Vineyard Escape

6. CIELO – The Sky Dome | A Peaceful Vineyard Escape

CIELO – The Sky Dome | A Peaceful Vineyard Escape
Windsor
The price is CA $153
CA $282 total
includes taxes & fees
Nov 5 - Nov 6
CIELO – The Sky Dome | A Peaceful Vineyard Escape

7. LUNA – The Moon Dome | A Romantic Vineyard Escape

LUNA – The Moon Dome | A Romantic Vineyard Escape
Windsor
The price is CA $153
CA $282 total
includes taxes & fees
Nov 5 - Nov 6
LUNA – The Moon Dome | A Romantic Vineyard Escape

8. VINO – The Wine Dome | Vineyard Retreat

VINO – The Wine Dome | Vineyard Retreat
Windsor
10.0 out of 10, Exceptional, (1 review)
"What an awesome experience! Amenities provided were great…basic toiletries, cooking spices, ample towels, and a very comfy, warm bed. Location was awesome since it was adjacent to Bent Ridge Winery/Brewery/Cidery. When we arrived around 3p, we visited the Bent Ridge restaurant for cider/beer flights, the Brie appy and pizzas (very, very good). Once we had our fill, we checked into the glamping dome and then returned back to Bent Ridge for dinner and live music- what an amazing first day in...
United States
Dean Bradley W.
The price is CA $178
CA $313 total
includes taxes & fees
Nov 9 - Nov 10
VINO – The Wine Dome | Vineyard Retreat

9. In Town - Summer St. Private Suite

In Town - Summer St. Private Suite
Wolfville
9.4 out of 10, Exceptional, (13 reviews)
"Had a great stay. Communication with the host was clear and easy to follow. Location is excellent for access to shops/restaurants. Our only ‘complaint’ was the bathroom is very cold! But other than that it was a very nice place to stay"
Canada
David
The price is CA $100
CA $230 total
includes taxes & fees
Nov 5 - Nov 6
In Town - Summer St. Private Suite

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

Studio-like Comfort in Wolfville’s Beating Heart
Wolfville
9.8 out of 10, Exceptional, (50 reviews)
"From check in to check out the staff was amazing and we will return Great job"
Canada
Corey
The price is CA $101
CA $231 total
includes taxes & fees
Nov 5 - Nov 6
Studio-like Comfort in Wolfville’s Beating Heart

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

Cozy Loft Bunkie | Sleeps 4 | BBQ + Fire Pit
Mount Uniacke
10.0 out of 10, Exceptional, (9 reviews)
"My family and I loved our stay in bunkie land!! Charmen was very welcoming and got us everything we needed. Our bunkie was small (as expected) but had all necessities and more. We made smores on the BBQ, bathrooms were entirely new and easily accessible and the hot tub was a must!! Such a cozy stay, would have definitely stayed longer ! Highly recommend!"
Canada
Victoria
The price is CA $116
CA $187 total
includes taxes & fees
Dec 1 - Dec 2
Cozy Loft Bunkie | Sleeps 4 | BBQ + Fire Pit

12. 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 CA $104
CA $174 total
includes taxes & fees
Dec 1 - Dec 2
Pet-Friendly Cabin | Sleeps 2 | Private Fire Pit

13. 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, (38 reviews)
"The location was excellent and clean and roomy. The people upstairs were a little noisy upstairs the last night but other than that, our stay was great."
United States
Colette P.
The price is CA $116
CA $260 total
includes taxes & fees
Nov 29 - Nov 30
In the Heart of Town - Private Ground Level Unit

14. Wolfville at your Doorstep

Wolfville at your Doorstep
Wolfville
9.6 out of 10, Exceptional, (33 reviews)
"Great place to stay.The excellent location, clean space and laundry facilities made our stay very enjoyable."
Canada
Mary Helen B.
The price is CA $101
CA $243 total
includes taxes & fees
Nov 23 - Nov 24
Wolfville at your Doorstep

15. 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, (5 reviews)
"Enjoyed my stay."
United States
Harry G.
The price is CA $167
CA $273 total
includes taxes & fees
Nov 24 - Nov 25
Suite 201 - Spacious One Bedroom Apartment-Style Suite in Hybrid Hotel Wolfville

16. Flamingo Suite (Downtown Wolfville)

Flamingo Suite (Downtown Wolfville)
Wolfville
9.2 out of 10, Wonderful, (7 reviews)
"Easy process and great location."
Canada
Jacob
The price is CA $201
CA $250 total
includes taxes & fees
Nov 5 - Nov 6
Flamingo Suite (Downtown Wolfville)

17. 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 $116
CA $263 total
includes taxes & fees
Nov 5 - Nov 6
Sunken Escapes Kenny's (Unit 5)

18. Bespoke Lake Cottage

Bespoke Lake Cottage
Kings County
9.2 out of 10, Wonderful, (12 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 $105
CA $311 total
includes taxes & fees
Nov 5 - Nov 6
Bespoke Lake Cottage

19. Gaspereau Suite -Jacuzzi, KngBd, DT

Gaspereau Suite -Jacuzzi, KngBd, DT
Wolfville
8.4 out of 10, Very good, (19 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 $178
CA $222 total
includes taxes & fees
Nov 5 - Nov 6
Gaspereau Suite -Jacuzzi, KngBd, DT

20. 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, (34 reviews)
"Great location. Very clean."
Canada
Sarah
The price is CA $136
CA $344 total
includes taxes & fees
Nov 5 - Nov 6
4 Wolfville's DT Core | Two Queen Bds+ Sofa Bed
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.