Windsor Holiday Rentals

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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 corner room with a TV, a clock, a sofa, a lamp, and a view of buildings through the window.

1. 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 NZ$266
includes taxes & fees
10 Nov - 11 Nov
Stylish Windsor Suite Near Wineries & Fundy Coast
A bedroom with a bed, a chair, a small table, a mirror, and a window with curtains.

2. Charming Windsor Suite | Walk to Shops & Dining

Charming Windsor Suite | Walk to Shops & Dining
Windsor
The price is NZ$276
includes taxes & fees
8 Dec - 9 Dec
Charming Windsor Suite | Walk to Shops & Dining
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, (1,337 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 NZ$248
includes taxes & fees
10 Nov - 11 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.

4. 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 NZ$441
includes taxes & fees
10 Nov - 11 Nov
VINO – The Wine Dome | Vineyard Retreat
Room

5. 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 NZ$453
includes taxes & fees
13 Nov - 14 Nov
Good place to call home for a week or so
A geodesic dome structure with a wooden deck and a view of the surrounding landscape.

6. StELLA – The Star Dome | Celestial Vineyard Escape

StELLA – The Star Dome | Celestial Vineyard Escape
Windsor
The price is NZ$441
includes taxes & fees
10 Nov - 11 Nov
StELLA – The Star Dome | Celestial Vineyard Escape
A modern interior with a large window, a fireplace, a television, and a sofa.

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

CIELO – The Sky Dome | A Peaceful Vineyard Escape
Windsor
The price is NZ$441
includes taxes & fees
10 Nov - 11 Nov
CIELO – The Sky Dome | A Peaceful Vineyard Escape
A modern living room with a curved ceiling, a black sofa, a coffee table, and a flat-screen TV.

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

LUNA – The Moon Dome | A Romantic Vineyard Escape
Windsor
The price is NZ$441
includes taxes & fees
10 Nov - 11 Nov
LUNA – The Moon Dome | A Romantic Vineyard Escape
A two-story house with a porch, a wooden door, and a number '5' sign.

9. 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 NZ$318
includes taxes & fees
10 Nov - 11 Nov
Flamingo Suite (Downtown 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 NZ$469
includes taxes & fees
10 Nov - 11 Nov
Downtown Wolfville Wine Country | 3rd Floor View 2BR & 3 Queen Beds
A modern kitchen with a central island, stainless steel appliances, and pendant lighting.

11. 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 NZ$394
includes taxes & fees
10 Nov - 11 Nov
Suite 302- One Bedroom apartment-style Suite w Balcony in Hybrid Hotel Wolfville
A modern kitchen with stainless steel appliances, wooden cabinets, and pendant lighting.

12. 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.
The price is NZ$429
includes taxes & fees
9 Dec - 10 Dec
Suite 304- Two Bedroom apartment-style Suite w Balcony in Hybrid Hotel Wolfville
A two-story house with a balcony, a patio with chairs and potted plants, and a large window.

13. 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 NZ$300
includes taxes & fees
10 Nov - 11 Nov
Gaspereau Suite -Jacuzzi, KngBd, DT
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.

14. 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 NZ$287
includes taxes & fees
18 Nov - 19 Nov
Studio-like Comfort in Wolfville’s Beating Heart
A living room with a round coffee table, a TV mounted on the wall, and a dining area with a small table and chairs.

15. 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 NZ$269
includes taxes & fees
11 Nov - 12 Nov
In Town - Summer St. Private Suite
A living room with a sofa set, a coffee table, a floor lamp, and a chandelier.

16. Wolfville at your Doorstep

Wolfville at your Doorstep
Wolfville
9.6 out of 10, Exceptional, (34 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 NZ$307
includes taxes & fees
11 Nov - 12 Nov
Wolfville at your Doorstep
A modern kitchen with a central island, stainless steel appliances, and pendant lighting.

17. 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 NZ$465
includes taxes & fees
24 Nov - 25 Nov
Suite 202- Two Bedroom apartment-style Suite w Balcony in Hybrid Hotel Wolfville
A spacious living room with a dark wood floor, a grey sofa, a coffee table, and a television on a wooden cabinet.

18. 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 NZ$319
includes taxes & fees
29 Nov - 30 Nov
In the Heart of Town - Private Ground Level Unit
A living room with two sofas, a coffee table, and a large plant.

19. 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 NZ$400
includes taxes & fees
10 Nov - 11 Nov
4 Wolfville's DT Core | Two Queen Bds+ Sofa Bed
A cabin with a deck, two red Adirondack chairs, and a fire pit.

20. 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 NZ$239
includes taxes & fees
10 Nov - 11 Nov
Cozy Loft Bunkie | Sleeps 4 | BBQ + Fire Pit
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

A building labeled 'The August House' with outdoor seating and string lights.
The August House

The August House

The August House
Windsor

10/10 Excellent

Nicely restored property with all that is needed except for a TV in the room but I expect this is on purpose to get you out of there. Location is good (walkable to pubs / restaurants) amenities are well thought out and a few little unexpected surprises. All in all the owners have done a great job with restoring a very old house!
Australia
Mark
Reviewed September 1, 2026
The August House

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, 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 NZ$221 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.