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Middleton Holiday Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Middleton holiday rentals

A modern kitchen with white cabinets, a stainless steel refrigerator, and a view of the sea through large windows.

1. Cottages on PEI

Cottages on PEI
2.5 star property
Chelton
9.6 out of 10, Exceptional, (146 reviews)
The price is NZ$244
includes taxes & fees
28 Oct - 29 Oct
Cottages on PEI
A two-story house with a large lawn and a tree with pink flowers.

2. Bridge View near Confederation Bridge and Beaches

Bridge View near Confederation Bridge and Beaches
Borden-Carleton
9.8 out of 10, Exceptional, (6 reviews)
"Clean and convenient. The host was so kind."
United States
Sarah E.
The price is NZ$270
includes taxes & fees
1 Nov - 2 Nov
Bridge View near Confederation Bridge and Beaches
A two-story house with a red roof, surrounded by lush greenery and a well-maintained lawn.

3. Garden View near Confederation Bridge and beaches

Garden View near Confederation Bridge and beaches
Borden-Carleton
8.4 out of 10, Very good, (6 reviews)
"Excellent location. The views from the backyard of the Confederation Bridge were wonderful. Easy drive to Summerside and Charlottestown, and of course Anne of Green Gables! PEI is strikingly beautiful.Host was very friendly and responsive. "Garden View" was very clean and modern. "
United States
Cheryl H.
The price is NZ$349
includes taxes & fees
1 Nov - 2 Nov
Garden View near Confederation Bridge and beaches
An aerial view of a residential area with multiple detached houses, a swimming pool, and a large green field.

4. Hidden Acres Cottages

Hidden Acres Cottages
3.5 star property
Cavendish
9.0 out of 10, Wonderful, (351 reviews)
"Friendly staff, Great location."
Canada
Edward
The price is NZ$229
includes taxes & fees
3 Oct - 4 Oct
Hidden Acres Cottages
A sauna with wooden benches and a stone wall in the center.

5. Cavendish Lodge & Cottages

Cavendish Lodge & Cottages
3.5 star property
Bayview
9.2 out of 10, Wonderful, (161 reviews)
"Great place to stay."
Canada
Shawn
Cavendish Lodge & Cottages
A marina with various boats docked, a pier, and a building with a Canadian flag.

6. Downtown Summerside Jewel

Downtown Summerside Jewel
Summerside, PE
9.4 out of 10, Exceptional, (34 reviews)
"Very clean. Well located. Super host."
Canada
Bruce
The price is NZ$277
includes taxes & fees
7 Oct - 8 Oct
Downtown Summerside Jewel
A single-story house with a covered porch, a red exterior, and a Canadian flag.

7. Spacious 3 BR Cottage, Quiet and Peaceful Inn The Woods Cottages PEI - Cottage 1

Spacious 3 BR Cottage, Quiet and Peaceful Inn The Woods Cottages PEI - Cottage 1
Kensington
10.0 out of 10, Exceptional, (21 reviews)
"Had a great stay. Place was quaint and clean. Easy check in and out. "
United States
Natalie S.
The price is NZ$345
includes taxes & fees
30 Oct - 31 Oct
Spacious 3 BR Cottage, Quiet and Peaceful Inn The Woods Cottages PEI - Cottage 1
A wooden boardwalk through a forest with tall trees and ferns.

8. SUMMERSIDE GEM

SUMMERSIDE GEM
Summerside
9.6 out of 10, Exceptional, (89 reviews)
"Great spot, well equipped and comfortable."
United States
Julie R.
The price is NZ$306
includes taxes & fees
7 Oct - 8 Oct
SUMMERSIDE GEM
A cozy cabin-style room with a wooden ceiling, a large window with curtains, a grey sofa with 'IN THE WOODS' cushions, a wooden coffee table, and a small wooden side table.

9. Cozy 2 BR Cottage close to Cavendish Inn The Woods Cottages PEI - Cottage 2

Cozy 2 BR Cottage close to Cavendish Inn The Woods Cottages PEI - Cottage 2
Kensington
9.2 out of 10, Wonderful, (26 reviews)
"Overall clean and cozy , shower was tight and I think there is a skunk living close by as we could smell skunk all weekend … Communication was great with the host, Check in smooth… Close to everything Great for temporary stays"
Canada
michelle
The price is NZ$313
includes taxes & fees
25 Oct - 26 Oct
Cozy 2 BR Cottage close to Cavendish Inn The Woods Cottages PEI - Cottage 2
A spacious kitchen with a wooden staircase, a dining area with a wooden table and chairs, and a view of the outdoors through large windows.

10. Avonlea Forest Hill Cottages

Avonlea Forest Hill Cottages
3.0 star property
Cavendish
9.0 out of 10, Wonderful, (33 reviews)
"Great stay!"
Canada
Steven
The price is NZ$257
includes taxes & fees
19 Oct - 20 Oct
Avonlea Forest Hill Cottages
A cozy living area with a wooden ceiling, a large wooden dining table with red chairs, a gray sofa, and a stone fireplace.

11. Avonlea Cottages

Avonlea Cottages
3.5 star property
Cavendish
8.4 out of 10, Very good, (264 reviews)
"Was great"
Canada
Sean
The price is NZ$239
includes taxes & fees
4 Oct - 5 Oct
Avonlea Cottages
A wooden barrel-shaped structure with a door and windows, a bench outside, and a stone pathway.

12. Cavendish Bosom Buddies Cottage Resort

Cavendish Bosom Buddies Cottage Resort
3.0 star property
Cavendish
9.4 out of 10, Exceptional, (212 reviews)
"Great stay!"
Canada
Shannon
The price is NZ$202
includes taxes & fees
19 Oct - 20 Oct
Cavendish Bosom Buddies Cottage Resort
A wooden cabin with a hot tub, large windows, and a welcome sign.

13. Rest Ashored in Anne's land!- Hot tub, Kayaks Centrally located, stunning views.

Rest Ashored in Anne's land!- Hot tub, Kayaks Centrally located, stunning views.
Kensington
9.8 out of 10, Exceptional, (31 reviews)
"The hot tub was perfect. Traveling in early spring we knew the weather could be cold or rainy. Having the hot tub to come back to was a relaxing and enjoyable end to our days."
Canada
Annette A.
The price is NZ$356
includes taxes & fees
11 Oct - 12 Oct
Rest Ashored in Anne's land!- Hot tub, Kayaks Centrally located, stunning views.
A coastal landscape with rocky cliffs and a sandy beach.

14. Wavie Waters Cottage! - King bed, Kayaks, Centrally located, stunning views.

Wavie Waters Cottage! - King bed, Kayaks, Centrally located, stunning views.
Kensington
10.0 out of 10, Exceptional, (47 reviews)
"way through Waters is a little piece of paradise 360 water views! really close to food and gas but out on its own in a pristine beautiful environment!"
United States
Rosanne R.
The price is NZ$350
includes taxes & fees
5 Oct - 6 Oct
Wavie Waters Cottage! - King bed, Kayaks, Centrally located, stunning views.
A portable grill on a wooden deck with a clear sky in the background.

15. Wood Duck Cottage

Wood Duck Cottage
3.5 star property
Cavendish
9.4 out of 10, Exceptional, (11 reviews)
"My family really enjoyed this cottage! Its very roomy, and close to everything. The cottage was very clean, modern, and felt like we were right at home! * Our only negative would be that the wifi was extremely slow so it was hard to connect the TV streaming services and use our phones. We will definitely be back! Our favorite spot we've stayed in cavendish yet!"
Canada
Tasha
The price is NZ$255
includes taxes & fees
10 Oct - 11 Oct
Wood Duck Cottage
A hot tub with a view of a house and trees.

16. Valley Pearl Suite | 2 BDRM sleeps 6, full kitchen

Valley Pearl Suite | 2 BDRM sleeps 6, full kitchen
Victoria
9.4 out of 10, Exceptional, (3 reviews)
"Great spot in a beautiful village. Easy walk anywhere you want to go."
United States
Thomas J.
The price is NZ$489
includes taxes & fees
1 Nov - 2 Nov
Valley Pearl Suite | 2 BDRM sleeps 6, full kitchen
A dining area with a wooden table and chairs, a sliding glass door leading to a deck, and a view of the outdoors.

17. Montgomery Cavendish Cottages

Montgomery Cavendish Cottages
3.5 star property
Cavendish
9.8 out of 10, Exceptional, (60 reviews)
"Extremely clean and in close proximity to main attractions."
Canada
Lucy
Montgomery Cavendish Cottages
A large house with a lawn and a body of water in the background.

18. Explore Anne's Land at Four Winds Cottage

Explore Anne's Land at Four Winds Cottage
Park Corner
10.0 out of 10, Exceptional, (1 review)
"My y family stayed here for almost a week. 4 adults and a 2 year young grandson. It is mind boggling that they(owner and trusted contractor/property manager)were able to transform a former woodshed and utility shed into a fully functional tiny home. There is likely going to be an updated picture in the dictionary for the words “cozy” and “inviting”!!!! The superhost’s attention to detail was brought to the forefront with phenomenal firsthand interaction with the property manager, any and all...
United States
Mike F.
The price is NZ$834
includes taxes & fees
6 Oct - 7 Oct
Explore Anne's Land at Four Winds Cottage
A covered porch with a stone accent wall, a dining table with chairs, and a 'No Smoking' sign on the door.

19. Hidden Gem 3 BR Cottage w/ Forest View Inn The Woods Cottages PEI - Cottage 3

Hidden Gem 3 BR Cottage w/ Forest View Inn The Woods Cottages PEI - Cottage 3
Kensington
9.6 out of 10, Exceptional, (22 reviews)
"Great location in the woods. Quiet and relaxing. The cabin had everything we needed and more. Les and Tammy were friendly and helpful with any questions we had. The location is off the beaten path but easy to get to. The entire property is very well maintained. This was one of the special parts of our first trip to PEI. We will definitely return."
Canada
Linda
The price is NZ$367
includes taxes & fees
1 Nov - 2 Nov
Hidden Gem 3 BR Cottage w/ Forest View Inn The Woods Cottages PEI - Cottage 3
An aerial view of a coastal area with sandbanks and a narrow strip of land with a rocky shoreline.

20. Bent Brook Beach House - Private, pet friendly, beach access, central location

Bent Brook Beach House - Private, pet friendly, beach access, central location
Murray Corner
9.8 out of 10, Exceptional, (10 reviews)
"Beautiful property. Extremely clean and hosts ensure that every little thing is taken care of. Thank you very much Carrie!"
Canada
Denys M.
The price is NZ$647
includes taxes & fees
28 Oct - 29 Oct
Bent Brook Beach House - Private, pet friendly, beach access, central location
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 Middleton Hotel Reviews

Loyalist Country Inn & Conference Centre

Loyalist Country Inn & Conference Centre

8/10 Good
"Met our needs"
Laura 1-night trip
Posted 2 hours ago
Loyalist Country Inn & Conference Centre

Find out more about Middleton

Everything you need to know about Middleton 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 Middleton 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 Middleton holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Middleton holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middleton. 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 Middleton 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 Middleton holiday rentals we have selected for you start as low as NZ$202 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Middleton rentals

At Expedia, we put the best Middleton 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 Middleton 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 Middleton 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 Middleton. 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 Middleton?

Yes, there are holiday rentals close to the most popular sights in Middleton, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Middleton has to offer?

Water Front 6BR Oasis w/ Hot Tub & Views, Near Victoria-by-the-Sea: This holiday home rental outside of Middleton offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of Access to hot tub in this rental home to help you unwind.

What’s there to see and do in Middleton?

Explore the area and family-friendly sights such as Haunted Mansion, or get out into nature at a spot like Chelton Beach Provincial Park. Port Borden Front Range Lighthouse and Anne of Green Gables Museum are a couple of places you'll find in the wider area.

What’s a holiday rental in Middleton like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Middleton. Holiday rentals offer extras such as patios, hot tubs and fire pits so your stay will be comfortable. If you're concerned about a sanitised environment, a holiday rental can offer a sense of privacy away from shared hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a great choice for families.