Windsor Holiday Rentals

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Check prices for these dates

Tonight
12 Dec - 13 Dec
Tomorrow
13 Dec - 14 Dec
This weekend
12 Dec - 14 Dec
Next weekend
19 Dec - 21 Dec

Our top choices for Windsor holiday rentals

Water view
Micro Boutique Living Wolfville

Apartment in Wolfville

Micro Boutique Living Wolfville
3.5 star property
9.0 out of 10, Wonderful, (1097)
"Loved staying here💕"
Canada
Deborah
The price is HK$1,066
HK$1,216 total
includes taxes & fees
16 Dec - 17 Dec
Micro Boutique Living Wolfville
Interior
Falls Lake Burrow - Private Cottage with Screened-in Hot Tub

Cottage in Windsor

Falls Lake Burrow - Private Cottage with Screened-in Hot Tub
10.0 out of 10, Exceptional, (40)
"Property is very well maintained, quiet and surrounded by nature. It’s a truly beautiful spot to spend a few relaxing days. "
Canada
Chris A.
Falls Lake Burrow - Private Cottage with Screened-in Hot Tub
Living area
Wolfville at your Doorstep

Apartment in Wolfville

Wolfville at your Doorstep
9.6 out of 10, Exceptional, (25)
"The place was clean and walkable to restaurants, shopping, the rink and the school. Mike would answer any questions I had very quickly. It was a great stay. "
Canada
Bonnie
The price is HK$609
HK$1,325 total
includes taxes & fees
15 Dec - 16 Dec
Wolfville at your Doorstep
Smart TV, books
Cottage by the lake - cozy escape

Cottage in Mount Uniacke

Cottage by the lake - cozy escape
9.8 out of 10, Exceptional, (7)
"Beautiful clean place with all the comforts of home! The host is an excellent communicator and had everything you could want for family fun! It was so serene and peaceful, and we highly recommend it!! Thank you Joelle for a wonderful stay at your beautiful treasure on the lake!"
United States
penny p.
Cottage by the lake - cozy escape
Fridge, microwave, oven, stovetop
Treeside Retreat with Hot tub

Holiday Home in Windsor

Treeside Retreat with Hot tub
10.0 out of 10, Exceptional, (45)
"Had a great vacation with our kiddos. They loved the private lake and cozy atmosphere. "
Canada
Kira W.
Treeside Retreat with Hot tub
Smart TV, fireplace, books, stereo
Beautiful Oceanfront Home on the Minas Basin

Holiday Home in Newport

Beautiful Oceanfront Home on the Minas Basin
10.0 out of 10, Exceptional, (44)
"A beautiful retreat, the view was incredible. We watched the tide coming in and out, an amazing sight!Our host was superhelpful- highly recommend this place"
Canada
amanda s.
The price is HK$1,016
HK$1,839 total
includes taxes & fees
13 Dec - 14 Dec
Beautiful Oceanfront Home on the Minas Basin
Smart TV
Beautiful Downtown Core Apt. Located on Main Street, Kentville

Apartment in Kentville

Beautiful Downtown Core Apt. Located on Main Street, Kentville
9.4 out of 10, Exceptional, (11)
"Excellent location and excellent host. Comfortable accommodations. "
Canada
Katherine I.
Beautiful Downtown Core Apt. Located on Main Street, Kentville
Terrace/patio
Leland’s Lakehouse

Holiday Home in Kings County

Leland’s Lakehouse
9.6 out of 10, Exceptional, (4)
"The cabin is in a fantastic location looking over the lake, the interior was very clean and looks great. Convinent location for getting to vineyards and wolfvile. I would highly recommend this place for anyone to stay at. "
Canada
Max D.
Leland’s Lakehouse
Property grounds
Chalet Drive - Lakefront Cottage

Cottage in Windsor

Chalet Drive - Lakefront Cottage
9.6 out of 10, Exceptional, (8)
"Great place. Very well stocked with everything that was needed. Beautiful place"
Canada
Jean G.
Chalet Drive - Lakefront Cottage
Living area
4 Wolfville's DT Core | Two Queen Bds+ Sofa Bed

Apartment in Wolfville

4 Wolfville's DT Core | Two Queen Bds+ Sofa Bed
9.4 out of 10, Exceptional, (18)
"Ease of check in and check out, very clean and location was perfect. "
Canada
Stacy T.
The price is HK$762
HK$1,730 total
includes taxes & fees
11 Jan - 12 Jan 2026
4 Wolfville's DT Core | Two Queen Bds+ Sofa Bed
Terrace/patio
Lakeside Retreat with Hot Tub

Holiday Home in Windsor

Lakeside Retreat with Hot Tub
9.4 out of 10, Exceptional, (27)
"Great stay overall"
United States
Shelley P.
Lakeside Retreat with Hot Tub
Property grounds
High end cozy retreat ideal for large families with wood stove & large firepit

Holiday Home in Smiths Corner

High end cozy retreat ideal for large families with wood stove & large firepit
9.8 out of 10, Exceptional, (88)
"Very comfy house . Wonderful location by the lake, perfect for family get together"
United Kingdom
annie g.
High end cozy retreat ideal for large families with wood stove & large firepit
Property grounds
Destination Lake House - Hot tub

Holiday Home in Windsor

Destination Lake House - Hot tub
10.0 out of 10, Exceptional, (1)
"Great spot"
Canada
Mark M.
The price is HK$2,363
HK$3,909 total
includes taxes & fees
16 Dec - 17 Dec
Destination Lake House - Hot tub
Smart TV
In the Heart of Town - Private Ground Level Unit

Apartment in Wolfville

In the Heart of Town - Private Ground Level Unit
9.4 out of 10, Exceptional, (23)
"Place was great. Clean and well equipped and an awesome location. Will stay again. Thanks."
Canada
David
The price is HK$542
HK$1,248 total
includes taxes & fees
14 Dec - 15 Dec
In the Heart of Town - Private Ground Level Unit
Fridge, microwave, oven, stovetop
Suite 201 - 470 Main

Apartment in Wolfville

Suite 201 - 470 Main
The price is HK$929
HK$1,604 total
includes taxes & fees
5 Jan - 6 Jan 2026
Suite 201 - 470 Main
1 bedroom, iron/ironing board, WiFi, bed sheets
Studio-like Comfort in Wolfville’s Beating Heart

Apartment in Wolfville

Studio-like Comfort in Wolfville’s Beating Heart
10.0 out of 10, Exceptional, (35)
"This property is in the heart of Wolfville and everything is in walking distance. "
Canada
Kim
The price is HK$513
HK$1,151 total
includes taxes & fees
27 Dec - 28 Dec
Studio-like Comfort in Wolfville’s Beating Heart
Fridge, microwave, oven, stovetop
Charming 2-bedroom Retreat in the Heart of the Annapolis Valley

Holiday Home in New Minas

Charming 2-bedroom Retreat in the Heart of the Annapolis Valley
9.0 out of 10, Wonderful, (2)
"Great location, excellent communication with host - exactly what we were hoping for."
Canada
Rob F.
The price is HK$685
HK$1,630 total
includes taxes & fees
19 Dec - 20 Dec
Charming 2-bedroom Retreat in the Heart of the Annapolis Valley
3 bedrooms
Perfect little house to enjoy

Holiday Home in Ellershouse

Perfect little house to enjoy
The price is HK$1,346
HK$2,119 total
includes taxes & fees
13 Dec - 14 Dec
Perfect little house to enjoy
3 bedrooms, iron/ironing board, travel cot, free WiFi
3 bedrooms 5 bed’s upper unit of duplex home

Holiday Home in Kentville

3 bedrooms 5 bed’s upper unit of duplex home
9.2 out of 10, Wonderful, (5)
"We were in Kentville for u15AAA Atlantic Baseball…it was around 4 minutes to the field. Great location for that!"
Canada
Jonathan H.
3 bedrooms 5 bed’s upper unit of duplex home
Fireplace, DVD player, books
Cozy, stylish, and surrounded by nature; Sojourn Hideaway is the perfect getaway

Cabin in Windsor

Cozy, stylish, and surrounded by nature; Sojourn Hideaway is the perfect getaway
9.8 out of 10, Exceptional, (7)
"Excellent place to stay, clean and comfortable. I highly recommend."
Canada
Cathy G.
Cozy, stylish, and surrounded by nature; Sojourn Hideaway is the perfect getaway
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

Super 8 by Wyndham Windsor NS

Super 8 by Wyndham Windsor NS

10/10 Excellent
"Yea"
Paula 2-night trip
Posted 4 days ago
Super 8 by Wyndham Windsor NS

Find out more about Windsor

Search for holiday rentals in Windsor on Expedia! You can easily find your home rentals, villas, holiday apartments in Windsor using one of the methods below:

  • View our selection of featured holiday rentals in Windsor
  • Use the map to find apartments and other holiday homes in the Windsor neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Windsor while they last

Look no further and take a look at our great range of rental properties in Windsor!

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?

Treeside Retreat with Hot tub: This holiday home rental outside of Windsor is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Kick off your shoes and enjoy yourself with a garden and 1 hot tub.

What can I see and do in Windsor?

Cultural attractions include West Hants Historical Society, whereas Windsor Hockey Heritage Centre is just one of the family-friendly sights. Other places in town to visit include Haliburton House Museum 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.