Holiday Rentals in Windsor

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Windsor holiday rentals

A bedroom with a large bed, white pillows, and a view of a body of water through a sliding glass door.

1. 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 €136
includes taxes & fees
22 Nov - 23 Nov
Micro Boutique Living Wolfville
A modern bedroom with a geometric ceiling design, a bed with a grey quilt, and a small table with a chair.

2. 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 €223
includes taxes & fees
14 Nov - 15 Nov
VINO – The Wine Dome | Vineyard Retreat
A bedroom with a large bed, a TV mounted on the wall, a window with a view, and a seating area with two chairs and a small table.

3. 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 €142
includes taxes & fees
30 Nov - 1 Dec
Studio-like Comfort in Wolfville’s Beating Heart
A double-decker bus in a vineyard with a red telephone booth.

4. 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 €167
includes taxes & fees
22 Nov - 23 Nov
In the Heart of Town - Private Ground Level Unit
A modern kitchen with a large island, pendant lights, and a view to the outside.

5. 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 €168
includes taxes & fees
1 Dec - 2 Dec
Suite 201 - Spacious One Bedroom Apartment-Style Suite in Hybrid Hotel Wolfville
Room

6. Good place to call home for a week or so

Good place to call home for a week or so
Ellershouse
10.0 out of 10, Exceptional, (1 review)
The price is €228
includes taxes & fees
14 Nov - 15 Nov
Good place to call home for a week or so
A double-decker bus in a vineyard with a red telephone booth.

7. Wolfville at your Doorstep

Wolfville at your Doorstep
Wolfville
9.6 out of 10, Exceptional, (35 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 €147
includes taxes & fees
29 Nov - 30 Nov
Wolfville at your Doorstep
A double-decker bus in a vineyard with a red telephone booth.

8. 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 €133
includes taxes & fees
13 Dec - 14 Dec
In Town - Summer St. Private Suite
A modern kitchen with a central island, stainless steel appliances, and pendant lighting.

9. 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
9.4 out of 10, Exceptional, (3 reviews)
"Always a pleasure to stay at Hotel Wofville"
Canada
Kelly
The price is €201
includes taxes & fees
14 Nov - 15 Nov
Suite 302- One Bedroom apartment-style Suite w Balcony in Hybrid Hotel Wolfville
A hallway with a patterned rug, a bench, a plant, and a wall-mounted rack.

10. 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.
The price is €241
includes taxes & fees
15 Nov - 16 Nov
Downtown Wolfville Wine Country | 3rd Floor View 2BR & 3 Queen Beds
A kitchen with wooden cabinets, a central island with stools, a microwave, and various potted plants.

11. Alligator Suite - downtown Wolfville

Alligator Suite - downtown Wolfville
Wolfville
8.6 out of 10, Excellent, (9 reviews)
"Excellent location"
Canada
Peter
The price is €167
includes taxes & fees
14 Nov - 15 Nov
Alligator Suite - downtown Wolfville
A modern kitchen with a central island, stainless steel appliances, and pendant lighting.

12. 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 €227
includes taxes & fees
29 Nov - 30 Nov
Suite 202- Two Bedroom apartment-style Suite w Balcony in Hybrid Hotel Wolfville
A cabin with a deck, two red Adirondack chairs, and a fire pit.

13. 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 €122
includes taxes & fees
15 Nov - 16 Nov
Cozy Loft Bunkie | Sleeps 4 | BBQ + Fire Pit
A cabin with a wooden exterior, a balcony, and a grill area.

14. 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 €176
includes taxes & fees
18 Nov - 19 Nov
Sunken Escapes Kenny's (Unit 5)
A double-decker bus in a vineyard with a red telephone booth.

15. 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, (35 reviews)
"Great location. Very clean."
Canada
Sarah
The price is €223
includes taxes & fees
18 Nov - 19 Nov
4 Wolfville's DT Core | Two Queen Bds+ Sofa Bed
A geodesic dome structure with a wooden deck and a view of the surrounding landscape.

16. StELLA – The Star Dome | Celestial Vineyard Escape

StELLA – The Star Dome | Celestial Vineyard Escape
Windsor
The price is €223
includes taxes & fees
14 Nov - 15 Nov
StELLA – The Star Dome | Celestial Vineyard Escape
A modern interior with a large window, a fireplace, a television, and a sofa.

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

CIELO – The Sky Dome | A Peaceful Vineyard Escape
Windsor
The price is €223
includes taxes & fees
19 Nov - 20 Nov
CIELO – The Sky Dome | A Peaceful Vineyard Escape
A wooden dock extending into a calm lake, surrounded by rocks and greenery.

18. CAIA Lakeside Retreat- Sunken Lake, NS

CAIA Lakeside Retreat- Sunken Lake, NS
Sunken Lake
9.4 out of 10, Exceptional, (17 reviews)
"Pet friendly"
Canada
Lori
The price is €217
includes taxes & fees
14 Nov - 15 Nov
CAIA Lakeside Retreat- Sunken Lake, NS
A modern living room with a curved ceiling, a black sofa, a coffee table, and a flat-screen TV.

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

LUNA – The Moon Dome | A Romantic Vineyard Escape
Windsor
The price is €223
includes taxes & fees
14 Nov - 15 Nov
LUNA – The Moon Dome | A Romantic Vineyard Escape
A two-story house with a balcony, a patio with chairs and potted plants, and a large window.

20. 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 €160
includes taxes & fees
15 Nov - 16 Nov
Gaspereau Suite -Jacuzzi, KngBd, DT
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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Find out more about Windsor

Everything you need to know about Windsor holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windsor holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windsor holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windsor holiday rentals we have selected for you start as low as €136 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor holiday 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 holiday.

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.

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 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 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.