Windsor Holiday Rentals from AU$179: Search Short-Term Rentals

Q: 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.

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In two weeks

In two months

In three months

In four months

Our top choices for Windsor holiday 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

Windsor

Heather H.

includes taxes & fees

4 Nov - 5 Nov

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

Windsor

includes taxes & fees

1 Dec - 2 Dec

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

3. Stylish Windsor Suite Near Wineries & Fundy Coast

Windsor

Lucie

includes taxes & fees

16 Nov - 17 Nov

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

4. Micro Boutique Living Wolfville

Wolfville

Ernesto

includes taxes & fees

15 Nov - 16 Nov

A geodesic dome structure with a wooden deck and a view of the surrounding landscape.

5. StELLA – The Star Dome | Celestial Vineyard Escape

Windsor

includes taxes & fees

4 Nov - 5 Nov

A modern interior with a large window, a fireplace, a television, and a sofa.

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

Windsor

includes taxes & fees

4 Nov - 5 Nov

A modern living room with a curved ceiling, a black sofa, a coffee table, and a flat-screen TV.

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

Windsor

includes taxes & fees

4 Nov - 5 Nov

A modern bedroom with a geometric ceiling design, a bed with a grey quilt, and a small table with a chair.

8. VINO – The Wine Dome | Vineyard Retreat

Windsor

"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...

Dean Bradley W.

includes taxes & fees

4 Nov - 5 Nov

A living room with a round coffee table, a TV mounted on the wall, and a dining area with a small table and chairs.

9. In Town - Summer St. Private Suite

Wolfville

David

includes taxes & fees

4 Nov - 5 Nov

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.

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

Wolfville

Corey

includes taxes & fees

4 Nov - 5 Nov

A cabin with a deck, two red Adirondack chairs, and a fire pit.

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

Mount Uniacke

Victoria

includes taxes & fees

1 Dec - 2 Dec

A cabin with a porch, outdoor seating, and string lights.

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

Mount Uniacke

Charie

includes taxes & fees

4 Nov - 5 Nov

A spacious living room with a dark wood floor, a grey sofa, a coffee table, and a television on a wooden cabinet.

13. In the Heart of Town - Private Ground Level Unit

Wolfville

Colette P.

includes taxes & fees

29 Nov - 30 Nov

A living room with a sofa set, a coffee table, a floor lamp, and a chandelier.

14. Wolfville at your Doorstep

Wolfville

Mary Helen B.

includes taxes & fees

23 Nov - 24 Nov

A modern kitchen with a large island, pendant lights, and a view to the outside.

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

Wolfville

Harry G.

includes taxes & fees

24 Nov - 25 Nov

A two-story house with a porch, a wooden door, and a number '5' sign.

16. Flamingo Suite (Downtown Wolfville)

Wolfville

Jacob

includes taxes & fees

12 Nov - 13 Nov

A cabin with a wooden exterior, a balcony, and a grill area.

17. Sunken Escapes Kenny's (Unit 5)

Sunken Lake

Murray

includes taxes & fees

29 Nov - 30 Nov

A cabin with a wooden deck, a small pond, and a gazebo.

18. Bespoke Lake Cottage

Kings County

Lily S.

includes taxes & fees

4 Nov - 5 Nov

A two-story house with a balcony, a patio with chairs and potted plants, and a large window.

19. Gaspereau Suite -Jacuzzi, KngBd, DT

Wolfville

William

includes taxes & fees

4 Nov - 5 Nov

A living room with two sofas, a coffee table, and a large plant.

20. 4 Wolfville's DT Core | Two Queen Bds+ Sofa Bed

Wolfville

Sarah

includes taxes & fees

16 Nov - 17 Nov

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Top Windsor Hotel Reviews

Old Orchard Inn

10/10 Excellent

"."

Cozy Loft Bunkie | Sleeps 4 | BBQ + Fire Pit

10/10 Excellent

"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!"

Beautiful Oceanfront Home on the Minas Basin

10/10 Excellent

"Wow!!!!We have just spent the most WONDERFUL 3 nights in Cheverie, Nova Scotia at the All Tides Inn. From the moment we parked and instantly checked out the view we knew that we had chosen the right property for our shore vacation. Spotlessly clean, well and thoughtfully stocked immenities, comfortable and the best location.... we cannot possibly recommend this rental more! Excellent for a couple, 2 couples, a family with or without pets - it's just simply perfect! There is a list of touristy options, restaurants, wineries to keep you as busy (or not) as you want. All Tides Inn is just absolutely FANTASTIC!! Love it"

Pet-Friendly Cabin | Sleeps 2 | Private Fire Pit

10/10 Excellent

"We stayed the weekend at the bunkies. It was great! The bunkies are so cute! They are so clean and everything you need for a peaceful time. The bathrooms are so nice and clean. We used the hot tub and we had a nice fire. I certainly would recommend this place. The hosts Danny and Charmane are wonderful, very friendly. We will be back!"

Family Bunkie | Sleeps 4 | Forest Views + Loft

10/10 Excellent

"Made our summer vacation perfect! My boyfriend doesn’t really care for cabins he prefers tent camping but said he wants to come back here and I agree it was a relaxing place, so quiet and cozy I was sad to go back home. The host was so nice and welcoming. All I can say is thank you so much I’m so excited to come back I loved my time at bunkie land!"

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 favourite 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 depend 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 AU$179 per night. Entering your travel dates in the search wizard might find you 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.

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Check prices for these dates

Our top choices for Windsor holiday rentals

1. Gateway to Annapolis Valley | Windsor Studio Suite

2. Charming Windsor Suite | Walk to Shops & Dining

3. Stylish Windsor Suite Near Wineries & Fundy Coast

4. Micro Boutique Living Wolfville

5. StELLA – The Star Dome | Celestial Vineyard Escape

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

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

8. VINO – The Wine Dome | Vineyard Retreat

9. In Town - Summer St. Private Suite

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

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

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

13. In the Heart of Town - Private Ground Level Unit

14. Wolfville at your Doorstep

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

16. Flamingo Suite (Downtown Wolfville)

17. Sunken Escapes Kenny's (Unit 5)

18. Bespoke Lake Cottage

19. Gaspereau Suite -Jacuzzi, KngBd, DT

20. 4 Wolfville's DT Core | Two Queen Bds+ Sofa Bed

Find holiday rentals that suit your style

Top Windsor Hotel Reviews

Old Orchard Inn

The Stella Rose B&B

The Breeze Motel

Farmhouse Inn B&B

Gateway to Annapolis Valley | Windsor Studio Suite

Cozy Loft Bunkie | Sleeps 4 | BBQ + Fire Pit

Beautiful Oceanfront Home on the Minas Basin

Pet-Friendly Cabin | Sleeps 2 | Private Fire Pit

Family Bunkie | Sleeps 4 | Forest Views + Loft

Find out more about Windsor

Frequently asked questions

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