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

Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Windsor vacation 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
$146 nightly
The price is $167
Oct 7 - Oct 8
Total with taxes and fees
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
$133 nightly
The price is $152
Oct 7 - Oct 8
Total with taxes and fees
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
$133 nightly
The price is $152
Oct 18 - Oct 19
Total with taxes and fees
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
$129 nightly
The price is $147
Oct 5 - Oct 6
Total with taxes and fees
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.
$123 nightly
The price is $141
Oct 6 - Oct 7
Total with taxes and fees
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
$269 nightly
The price is $306
Oct 19 - Oct 20
Total with taxes and fees
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
$191 nightly
The price is $217
Oct 6 - Oct 7
Total with taxes and fees
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
$250 nightly
The price is $285
Oct 4 - Oct 5
Total with taxes and fees
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
9.4 out of 10, Exceptional, (3 reviews)
"It was a great stay in a great location!"
United States
Craig M.
$310 nightly
The price is $353
Oct 4 - Oct 5
Total with taxes and fees
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.
$354 nightly
The price is $403
Oct 2 - Oct 3
Total with taxes and fees
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.
$249 nightly
The price is $277
Oct 28 - Oct 29
Total with taxes and fees
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.
$196 nightly
The price is $223
Oct 4 - Oct 5
Total with taxes and fees
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.
$250 nightly
The price is $278
Oct 26 - Oct 27
Total with taxes and fees
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.
$340 nightly
The price is $380
Oct 20 - Oct 21
Total with taxes and fees
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
$214 nightly
The price is $243
Oct 19 - Oct 20
Total with taxes and fees
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
$169 nightly
The price is $192
Oct 4 - Oct 5
Total with taxes and fees
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
$116 nightly
The price is $132
Oct 6 - Oct 7
Total with taxes and fees
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.
$209 nightly
The price is $238
Oct 26 - Oct 27
Total with taxes and fees
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
$115 nightly
The price is $131
Oct 6 - Oct 7
Total with taxes and fees
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)
$230 nightly
The price is $263
Oct 1 - Oct 2
Total with taxes and fees
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

The August House

The August House

10/10 Excellent
"Superb amenities and stay ."
Eric 1-night trip
Posted 3 hours ago
The August House

Find out more about Windsor

Everything you need to know about Windsor vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windsor vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windsor. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Windsor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $122 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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.