Windsor Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Windsor Vacation Homes

Gaspereau Suite - 2 Seat Jacuzzi, KingBd, Downtown
Relax in a spacious bathroom with a bathtub, wooden bench, and table with a lamp.

Gaspereau Suite - 2 Seat Jacuzzi, KingBd, Downtown

9.2 out of 10, Wonderful, (10)
"Great stay. Will definitely be back!"
The price is CA $235
CA $274 total
includes taxes & fees
Aug 13 - Aug 14
Gaspereau Suite - 2 Seat Jacuzzi, KingBd, Downtown
Beautiful Oceanfront Home on the Minas Basin
Relax on the deck with a view of the surrounding landscape and water.

Beautiful Oceanfront Home on the Minas Basin

10.0 out of 10, Exceptional, (31)
"Such an amazing stay! The view was incredible and the house was gorgeous. Hosts were also awesome and great communicators. Would highly recommend!"
Beautiful Oceanfront Home on the Minas Basin
Charming 2-bedroom Retreat with AC, WiFi in the Heart of the Annapolis Valley
Terrace/patio

Charming 2-bedroom Retreat with AC, WiFi in the Heart of the Annapolis Valley

Charming 2-bedroom Retreat with AC, WiFi in the Heart of the Annapolis Valley
Beautiful 2 bedroom residential home in Kentville
Efficient kitchen with microwave, coffee maker, and stove, perfect for cooking and meal prep.

Beautiful 2 bedroom residential home in Kentville

7.8 out of 10, Good, (6)
"i have really enjoyed the property it was clean and was exactly what we were looking for...the location for our golfing 4 days was great...it could use a bbq. the tv system is deplorable no news and barely any sports"
The price is CA $180
CA $311 total
includes taxes & fees
Aug 17 - Aug 18
Beautiful 2 bedroom residential home in Kentville
3 Bedroom House- Refined Elegance
Enjoy a spacious open-plan living space with a kitchen, dining area, and living room, featuring a refrigerator, large island, and comfortable sofa.

3 Bedroom House- Refined Elegance

10.0 out of 10, Exceptional, (2)
"Clean and great amenities. "
The price is CA $395
CA $602 total
includes taxes & fees
Aug 13 - Aug 14
3 Bedroom House- Refined Elegance
Upper Unit 1067 Rawding
Enjoy meals in this kitchen with a view, featuring a large window overlooking the outdoors.

Upper Unit 1067 Rawding

9.6 out of 10, Exceptional, (9)
"Very clean, very nice amenities. Perfect for our weekend trip."
Upper Unit 1067 Rawding
Treeside Retreat with Hot tub
Enjoy cooking in this well-equipped kitchen with a dining table and stainless steel appliances.

Treeside Retreat with Hot tub

10.0 out of 10, Exceptional, (39)
"It was amazing time ! "
The price is CA $361
CA $580 total
includes taxes & fees
Aug 24 - Aug 25
Treeside Retreat with Hot tub
CAIA Lakeside Retreat- Sunken Lake, NS
Enjoy a serene view of the water from this deck, surrounded by trees and a distant shoreline.

CAIA Lakeside Retreat- Sunken Lake, NS

9.4 out of 10, Exceptional, (9)
"My wife and dogs loved this property which is right in the center of Wolfville. I would definitely stay here again."
The price is CA $236
CA $462 total
includes taxes & fees
Aug 11 - Aug 12
CAIA Lakeside Retreat- Sunken Lake, NS
Darling downtown micro suite!
Stunning two-story home with a gabled roof, surrounded by a lush garden and vibrant greenery.

Darling downtown micro suite!

8.6 out of 10, Excellent, (4)
"Great overnight rental!"
The price is CA $155
CA $208 total
includes taxes & fees
Aug 18 - Aug 19
Darling downtown micro suite!
Leland’s Lakehouse
Relax on the deck overlooking the serene lake surrounded by dense forest.

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. "
The price is CA $237
CA $435 total
includes taxes & fees
Sep 3 - Sep 4
Leland’s Lakehouse
Bespoke Lake Cottage
Cozy living area with a fireplace, large window, and comfortable seating options.

Bespoke Lake Cottage

9.6 out of 10, Exceptional, (7)
"We have a lovely stay - our only complaint is that we didn't book for long enough! The cottage is very charming and very clean. Bed is comfortable and kitchen had all equipment needed for food prep. "
The price is CA $230
CA $408 total
includes taxes & fees
Sep 1 - Sep 2
Bespoke Lake Cottage
Sunken Escapes #3 Kit's Retreat
1 bedroom, WiFi

Sunken Escapes #3 Kit's Retreat

The price is CA $188
CA $372 total
includes taxes & fees
Sep 3 - Sep 4
Sunken Escapes #3 Kit's Retreat
Elegant 3 Bedroom House
Relax in a spacious living area with a sofa set and flat-screen TV, or enjoy a meal at the dining table with a view of the outdoors.

Elegant 3 Bedroom House

The price is CA $395
CA $602 total
includes taxes & fees
Aug 11 - Aug 12
Elegant 3 Bedroom House
Beutiful 3 bedroom upper unit of duplex home
Enjoy al fresco dining on this deck with a grill and comfortable seating for four.

Beutiful 3 bedroom upper unit of duplex home

9.4 out of 10, Exceptional, (3)
"We were in Kentville for u15AAA Atlantic Baseball…it was around 4 minutes to the field. Great location for that!"
Beutiful 3 bedroom upper unit of duplex home
Beautiful, private oceanfront cottage on the Bay of Fundy
Surrounded by vibrant purple lupine flowers and lush greenery, this garden offers a serene escape.

Beautiful, private oceanfront cottage on the Bay of Fundy

9.8 out of 10, Exceptional, (52)
"Property is very nice. Neighbors were very friendly. "
Beautiful, private oceanfront cottage on the Bay of Fundy
Lakeside Retreat with Hot Tub
Relax by the fire pit in a serene forest setting, surrounded by trees and a cozy cabin.

Lakeside Retreat with Hot Tub

9.2 out of 10, Wonderful, (22)
"Our family of five had a great stay at this cottage in the country and thoroughly enjoyed the hot tub. Would definitely stay here again!"
The price is CA $438
CA $681 total
includes taxes & fees
Aug 28 - Aug 29
Lakeside Retreat with Hot Tub
High end cozy retreat ideal for large families with wood stove & large firepit
Enjoy cooking in this well-equipped kitchen with a large island, appliances, and ample counter space.

High end cozy retreat ideal for large families with wood stove & large firepit

9.8 out of 10, Exceptional, (87)
"Very comfy house . Wonderful location by the lake, perfect for family get together"
High end cozy retreat ideal for large families with wood stove & large firepit
Perfect little house to enjoy
Enjoy meals in the kitchen with a dining table and chairs, microwave, and stove.

Perfect little house to enjoy

The price is CA $239
CA $376 total
includes taxes & fees
Aug 10 - Aug 11
Perfect little house to enjoy
Lower Unit 1067 Rawding
Enjoy cooking in this well-equipped kitchen with a refrigerator, microwave, and oven.

Lower Unit 1067 Rawding

10.0 out of 10, Exceptional, (5)
"Clean, close to town, overall a great place to stay with family or friends "
Lower Unit 1067 Rawding
Little Yellow House In The Heart Of The Valley 🏠
Exterior

Little Yellow House In The Heart Of The Valley 🏠

7.4 out of 10, Good, (3)
"I had such a wonderful stay here! The hosts were extremely friendly and easy to communicate with. The location was great, and just a short drive away from anything needed. House was well equipped with everything necessary. Would definitely recommend, and would stay again! "
Little Yellow House In The Heart Of The Valley 🏠
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windsor Hotel Reviews

Old Orchard Inn & Spa

Old Orchard Inn & Spa

10/10 Excellent
"Food is great"
Richard 1-night trip
Posted 10 hours ago
Old Orchard Inn & Spa