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Middleton Vacation Rentals

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Check prices for these dates

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

Our top choices for Middleton vacation 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)
"Super spot to stay. Loved the walks on the beach and sun set"
Canada
Clarence
$119 nightly
The price is $137
Oct 4 - Oct 5
Total with taxes and fees
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.
$132 nightly
The price is $152
Nov 1 - Nov 2
Total with taxes and fees
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.
$172 nightly
The price is $198
Nov 1 - Nov 2
Total with taxes and fees
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
$112 nightly
The price is $128
Oct 4 - Oct 5
Total with taxes and fees
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
$136 nightly
The price is $156
Oct 11 - Oct 12
Total with taxes and fees
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.
$171 nightly
The price is $197
Oct 25 - Oct 26
Total with taxes and fees
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.
$150 nightly
The price is $172
Oct 11 - Oct 12
Total with taxes and fees
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
$153 nightly
The price is $176
Oct 15 - Oct 16
Total with taxes and fees
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
$115 nightly
The price is $132
Oct 18 - Oct 19
Total with taxes and fees
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
$117 nightly
The price is $135
Oct 4 - Oct 5
Total with taxes and fees
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
$99 nightly
The price is $114
Oct 13 - Oct 14
Total with taxes and fees
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.
$177 nightly
The price is $204
Oct 4 - Oct 5
Total with taxes and fees
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.
$202 nightly
The price is $232
Oct 14 - Oct 15
Total with taxes and fees
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
$126 nightly
The price is $145
Oct 9 - Oct 10
Total with taxes and fees
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.
$238 nightly
The price is $280
Nov 1 - Nov 2
Total with taxes and fees
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.
$410 nightly
The price is $471
Oct 6 - Oct 7
Total with taxes and fees
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
$180 nightly
The price is $207
Nov 1 - Nov 2
Total with taxes and fees
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.
$293 nightly
The price is $337
Oct 15 - Oct 16
Total with taxes and fees
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 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 Middleton 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 Middleton vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Middleton vacation 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 low season months. For more hustle and bustle, you may prefer to visit Middleton 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 $114 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 Middleton rentals

At Expedia, we put the best Middleton 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 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 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 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 vacation rentals in Middleton?

Yes, you can find vacation rentals close to popular attractions in Middleton, or you can go with a secluded option if you want a relaxing place to stay.

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

Water Front 6BR Oasis w/ Hot Tub & Views, Near Victoria-by-the-Sea: Visitors like this Middleton vacation home rental. It offers a patio, a garden, and a barbecue grill 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 you can cook with friends or family. Make the most of the 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 larger area.

What’s a vacation rental in Middleton like?

A vacation rental is a private property where you can stay for a couple of days or more in Middleton. Vacation rentals feature amenities like laundry facilities and kitchens so you'll feel right at home. If you're concerned about cleanliness, vacation rentals can provide a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a popular choice for family trips.