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Windermere Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Windermere vacation rentals

A bedroom with a bed, a chair, a desk, and a door.

1. Sakura Valley Studio Suite #4 / Private Entrance in beautiful Annapolis Valley

Sakura Valley Studio Suite #4 / Private Entrance in beautiful Annapolis Valley
North Alton
10.0 out of 10, Exceptional, (6 reviews)
"The host was incredible; quick responses and happy to accommodate special requests. Will be staying here again for sure!"
Canada
Gillian
$117 nightly
The price is $133
Oct 19 - Oct 20
Total with taxes and fees
Sakura Valley Studio Suite #4 / Private Entrance in beautiful Annapolis Valley
A coastal property with a large house, a driveway, and a grassy area.

2. Unit 1: Oceanfront 1BR / Pet-Friendly Escape

Unit 1: Oceanfront 1BR / Pet-Friendly Escape
Centreville
8.4 out of 10, Very good, (27 reviews)
"The location and peaceful was was exactly what was needed."
Canada
Tiffany E.
$113 nightly
The price is $129
Oct 25 - Oct 26
Total with taxes and fees
Unit 1: Oceanfront 1BR / Pet-Friendly Escape
A wooden deck with two hammock swings overlooking a lake.

3. Bespoke Lake Cottage

Bespoke Lake Cottage
Kings County
9.2 out of 10, Wonderful, (11 reviews)
"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. "
Canada
Lily S.
$206 nightly
The price is $235
Nov 1 - Nov 2
Total with taxes and fees
Bespoke Lake Cottage
A cabin with a wooden exterior, a balcony, and a grill area.

4. 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
$174 nightly
The price is $197
Nov 4 - Nov 5
Total with taxes and fees
Sunken Escapes Kenny's (Unit 5)
An outdoor grill area with a table and chairs, surrounded by trees.

5. Sakura Valley Studio Suite #7 / Private Entrance in beautiful Annapolis Valley

Sakura Valley Studio Suite #7 / Private Entrance in beautiful Annapolis Valley
North Alton
10.0 out of 10, Exceptional, (2 reviews)
"First, the host is FANTASTIC! This was my first non-hotel experience and she made it a great one! Extremely helpful! The unit was super clean and very nice for its size! Exactlyas show!, No smells at all! I would highly recommend your stay here! I will be booking a different unit next time just to experience more of these beautiful units!"
Canada
Lori
$123 nightly
The price is $140
Oct 24 - Oct 25
Total with taxes and fees
Sakura Valley Studio Suite #7 / Private Entrance in beautiful Annapolis Valley
A two-story building with a balcony and multiple windows.

6. Sakura Valley Studio Suite #2 / Private Entrance in beautiful Annapolis Valley

Sakura Valley Studio Suite #2 / Private Entrance in beautiful Annapolis Valley
North Alton
10.0 out of 10, Exceptional, (4 reviews)
"The property was clean and very well put together, very new and modern would definitely stay there again"
Canada
Ryan
$117 nightly
The price is $133
Oct 21 - Oct 22
Total with taxes and fees
Sakura Valley Studio Suite #2 / Private Entrance in beautiful Annapolis Valley
A single bed with a beige quilt, a white pillow, a wooden nightstand with a clock, a lamp, and a framed picture.

7. Sakura Valley Studio Suite #9 / Private Entrance in beautiful Annapolis Valley

Sakura Valley Studio Suite #9 / Private Entrance in beautiful Annapolis Valley
North Alton
10.0 out of 10, Exceptional, (2 reviews)
"Very clean and simple place for a reasonable price."
Canada
Ella Marie a.
$116 nightly
The price is $133
Oct 24 - Oct 25
Total with taxes and fees
Sakura Valley Studio Suite #9 / Private Entrance in beautiful Annapolis Valley
A wooden deck with a grill and picnic table, overlooking a lake with trees and a dock.

8. Archie's Lakeside Cabin

Archie's Lakeside Cabin
Kings County
7.4 out of 10, Good, (9 reviews)
"Great stay!"
Canada
Ashwin K.
$227 nightly
The price is $258
Oct 19 - Oct 20
Total with taxes and fees
Archie's Lakeside Cabin
A kitchenette with a stainless steel refrigerator, a coffee maker on the counter, and a flat-screen TV mounted on the wall.

9. Sakura Valley Studio Suite #3 / Private Entrance in beautiful Annapolis Valley

Sakura Valley Studio Suite #3 / Private Entrance in beautiful Annapolis Valley
North Alton
9.0 out of 10, Wonderful, (6 reviews)
"So glad we chose to stay at Sakura Valley! Highly recommend! The host is lovely and accommodating, the suite was very clean, beds comfortable. Location is great! It feels secluded but is close to the highway. I would definitely stay again."
Canada
Nadia
$114 nightly
The price is $129
Oct 19 - Oct 20
Total with taxes and fees
Sakura Valley Studio Suite #3 / Private Entrance in beautiful Annapolis Valley
A two-story building with a balcony and multiple windows.

10. Sakura Valley Studio Suite #1 / Private Entrance in beautiful Annapolis Valley

Sakura Valley Studio Suite #1 / Private Entrance in beautiful Annapolis Valley
North Alton
10.0 out of 10, Exceptional, (10 reviews)
"Absolutely stunning facility ! Would recommend 100% would stay again. The hosts were amazing. Loved that it was very scent free ! Everything was spotless. High end and had the best sleep of my whole trip"
Canada
Amanda
$127 nightly
The price is $144
Oct 25 - Oct 26
Total with taxes and fees
Sakura Valley Studio Suite #1 / Private Entrance in beautiful Annapolis Valley
A wooden bedside table with a lamp, a small potted plant, and a bed with white bedding.

11. Sakura Valley Studio Suite #6 / Private Entrance in beautiful Annapolis Valley

Sakura Valley Studio Suite #6 / Private Entrance in beautiful Annapolis Valley
North Alton
9.6 out of 10, Exceptional, (4 reviews)
"Great little spot. Tracy was very kind and accomadating. Would 100% recommend."
Canada
Byron
$133 nightly
The price is $152
Oct 24 - Oct 25
Total with taxes and fees
Sakura Valley Studio Suite #6 / Private Entrance in beautiful Annapolis Valley
A wooden deck with a bench, overlooking a lake surrounded by trees.

12. Leland’s Lakehouse

Leland’s Lakehouse
Kings County
9.4 out of 10, Exceptional, (8 reviews)
"Private and quiet Cozy and cute Place was well maintained Easy to find Very clean Super close to the lake Wonderful hot tub"
Canada
Nicole C.
$224 nightly
The price is $255
Nov 1 - Nov 2
Total with taxes and fees
Leland’s Lakehouse
A wooden dock extending into a calm lake, surrounded by rocks and greenery.

13. 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
$215 nightly
The price is $244
Nov 1 - Nov 2
Total with taxes and fees
CAIA Lakeside Retreat- Sunken Lake, NS
An outdoor patio with a grill, two chairs, and a table.

14. Sakura Valley Studio Suite #8 / Private Entrance in beautiful Annapolis Valley

Sakura Valley Studio Suite #8 / Private Entrance in beautiful Annapolis Valley
North Alton
$123 nightly
The price is $140
Oct 25 - Oct 26
Total with taxes and fees
Sakura Valley Studio Suite #8 / Private Entrance in beautiful Annapolis Valley
A bathroom with a wooden cabinet, a mirror, a ship's wheel decoration, and a welcome sign.

15. Sakura Valley Studio Suite #10 / Private Entrance in beautiful Annapolis Valley

Sakura Valley Studio Suite #10 / Private Entrance in beautiful Annapolis Valley
North Alton
$130 nightly
The price is $148
Oct 24 - Oct 25
Total with taxes and fees
Sakura Valley Studio Suite #10 / Private Entrance in beautiful Annapolis Valley
A wooden cabin bathroom with a shower, a small sink, and a wooden stool.

16. Sunken Escapes ZEEK (Unit 6)

Sunken Escapes ZEEK (Unit 6)
Sunken Lake
9.4 out of 10, Exceptional, (3 reviews)
"Beautifully crafted cabins. We used the accessible cabin for the most part. It had everything we needed for a tranquil adventure. The host went above and beyond to accomodate our needs. Much thanks."
Canada
Toni M.
$136 nightly
The price is $155
Nov 4 - Nov 5
Total with taxes and fees
Sunken Escapes ZEEK (Unit 6)
A bedroom with a large bed, white pillows, and a view of a body of water through a sliding glass door.

17. Micro Boutique Living Wolfville

Micro Boutique Living Wolfville
3.5 star property
Wolfville
9.0 out of 10, Wonderful, (1,335 reviews)
"Location is perfect"
Canada
Kelly
$134 nightly
The price is $152
Oct 27 - Oct 28
Total with taxes and fees
Micro Boutique Living Wolfville
A cozy, circular tent-style accommodation with a kitchenette, a sofa, and a dining area, surrounded by a forest.

18. Sunken Escapes #3 Kit's Retreat

Sunken Escapes #3 Kit's Retreat
Kings County
8.0 out of 10, Very good, (2 reviews)
"We came for the marathon and brought our granddaughter. The property exceeded expectations; it was clean comfortable and a joy to stay in. We had a great time and will definitely be back again if we stay in the area."
Canada
Jason T.
$198 nightly
The price is $225
Nov 8 - Nov 9
Total with taxes and fees
Sunken Escapes #3 Kit's Retreat
A view through a window of a lake with a forested shoreline and a clear sky.

19. Sunken Escapes Bunny Cabin #10

Sunken Escapes Bunny Cabin #10
Sunken Lake
8.0 out of 10, Very good, (2 reviews)
"It was great. I know having the bathroom and showers in different spot was different but still loved it. In touch with nature. A great place to stay. Room was cozy. My cat liked it. Knowing about the other spaces will make us want to choose one of them. This is what I needed and quiet place plus comfortable bed. Would stay again."
Canada
Monica S.
$116 nightly
The price is $131
Nov 4 - Nov 5
Total with taxes and fees
Sunken Escapes Bunny Cabin #10
A view through a window of a lake with a forested shoreline and a clear sky.

20. Sunken Escapes Glamping Unit #2

Sunken Escapes Glamping Unit #2
Sunken Lake
$174 nightly
The price is $197
Nov 3 - Nov 4
Total with taxes and fees
Sunken Escapes Glamping Unit #2
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 Windermere Hotel Reviews

Old Orchard Inn

Old Orchard Inn

10/10 Excellent
"All went great, with the exception of a very congested reception area."
Helen 1-night trip
Posted 4 hours ago
Old Orchard Inn

Find out more about Windermere

Everything you need to know about Windermere vacation rentals

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

Windermere vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windermere. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Windermere in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $129 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Windermere rentals

At Expedia, we put the best Windermere vacation 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 Windermere 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 Windermere vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windermere. 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

Can I find vacation rentals in Windermere?

Yes, we have vacation rentals near well known local attractions in Windermere, or you can go with a secluded option if you want a relaxing place to stay.

What are some of the best vacation home rentals in Windermere?

Foot of the Mountain Farmhouse-great location for exploring the valley!: You might want to consider this vacation home rental near Windermere, which is located in the mountains and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

What can I see and do in Windermere?

While exploring the area, visit family-friendly sights like Lockhart and Ryan Memorial Park, or get outside and enjoy nature at Kentville Bird Sanctuary. Valley Drive-In and Black Rock Lighthouse are a couple of places you'll find in the larger area.

What are vacation rentals like in Windermere?

Vacation rentals are privately owned accommodations you can stay in for several days or more in Windermere. Vacation rentals provide amenities such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of security away from public hotel elevators and busy concierge desks while still allowing you to travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular option for a small group gathering.