Holiday houses in Winsloe South

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Top-rated holiday rentals in Winsloe South

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite

A modern two-story home features a spacious balcony with glass railing and outdoor seating. Lush green grass surrounds the property, while trees provide natural landscaping. The structure showcases an angled roof, integrating natural materials for a seamless connection with the environment.

Guesthouse in Downtown Charlottetown

4.89 out of 5 average rating, 209 reviews

Wharfside - Waterfront + Downtown + Victoria Park

Unwind in this newly built main level suite overlooking the Charlottetown Harbour and the picturesque Victoria Park and just a short stroll to downtown shops & restaurants. Modern architecture at its finest, this loft has spared no expense. Floor to ceiling windows look out to sailboats and sunsets. Appointed with the luxury traveller in mind, this home is equipped with high end appliances, marble countertops, luxury linens and a king size bed for a truly restful sleep and stay. License #4000033

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Guest favourite

Aerial view showcases the cottage nestled within a vibrant forest, surrounded by trees and greenery. The nearby Brackley Bay glistens in the distance, offering a serene backdrop to the property. The expansive area around the cottage features landscaped outdoors, enhancing the sense of privacy and nature.

Cottage in Brackley Beach

4.93 out of 5 average rating, 81 reviews

Nestled Woods by Brackley Beach

Nestled in the woods by Brackley Bay, & close to Brackley Beach; comfortably relax amongst the trees. Minutes away from; world famous Brackley Beach, Brackley drive-in, Shirley's (Best burgers!), Dunes Cafe, Richards Seafood, Dalvay by the Sea and Charlottetown airport. Enjoy a private deck with a Webber bbq, upper deck off your master bedroom, & 1.5 bathrooms, with a 3 bedroom cottage-home of your own! *The basement is a separately rented unit, with a soundproof ceiling & separate entrance.*

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Superhost

Tiny home in Crapaud

5.0 out of 5 average rating, 7 reviews

The Oat Bin - accessible silo cabin with hot tub

Hawthorne Creek Silos: a unique retreat where agriculture meets hospitality. We’ve transformed three authentic grain tanks into stunning, luxury silos. Nestled in nature, each silo combines rugged heritage with boutique sophistication—offering a private, immersive getaway you won't find elsewhere. Private hot tubs, barrel sauna, loft with king bed and field views: reclaim your time, reconnect with nature, and experience country living, redefined. The Barley Bin, The Oat Bin, and The Wheat Bin

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Guest favourite

A large waterfront home is positioned on lush green grass, with scenic views of the water. The building features a neutral exterior and a sloped roof, framed by a clear sky. A driveway leads toward the house, enhancing accessibility.

Home in Marshfield

4.95 out of 5 average rating, 61 reviews

Beau View River House

Welcome to our beautiful waterfront property located just 10 minutes from downtown Charlottetown and 15 minutes to PEI's world renowned North Shore beaches! With 4 bedrooms and 3 baths, our large and private countryside rental has everything you need for a relaxing vacation with family and friends. Enjoy the spacious outdoors playing lawn games, having a campfire or relaxing on the deck. Spend your time indoors in our cozy, open concept living area or playing pool or ping pong in the game room.

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Top Guest favourite

The chalet's exterior is framed by trees, illuminated by soft lights from large windows. A rustic wooden facade complements the surrounding natural landscape, with a rocky foreground made up of earthy tones. The setting conveys a sense of privacy amidst nature.

Chalet in Brookvale

4.97 out of 5 average rating, 97 reviews

Loma Chalet - Nature Hideaway & Hot Tub

Located metres from the Mark Arendz Provincial Park. Enjoy ski-out Alpine and Nordic trails (winter) and extensive mountain bike trails (spring through fall). Nestled on 8 acres of forest for ultimate privacy. This four seasons chalet features: fully loaded kitchen, 3 bedrooms, bathroom, laundry, wood stove, fire pit and patio and new hot tub. Off-grid feel with all the amenities - perfect those looking to relax in nature. AWD/Snowmobile/Hike or assisted check-in required for winter access.

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Top Guest favourite

A neighborhood scene features a vibrant rainbow arching over several houses, creating a colorful contrast against a cloudy sky. Power lines traverse the image, with wet pavement reflecting the greenery surrounding the homes.

Apartment in Charlottetown

4.87 out of 5 average rating, 263 reviews

Charlottetown brand-new suite

This brand-new basement suite is modern and stylish. Our location is ideal for tourists. 5 minutes from airport. 15 minutes drive to downtown Charlottetown where guests can explore historic sites. 15 minutes drive to Brackley Beach, one of the largest and popular beach in PEI. This newly built basement suite is fully furnished with modern amenities, offering guests a comfortable and convenient stay. We take pride in providing guests with a clean and welcoming environment.

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Guest favourite

A ranch-style house is depicted against a backdrop of trees, showcasing an expansive front lawn. The exterior features a smooth surface with a prominent arch window at the center, flanked by symmetric landscaping and entrance doors. Cloudy skies create a serene atmosphere.

Home in Milton Station

5.0 out of 5 average rating, 10 reviews

Cozy/Private Home away from Home

Glengyle Lane is a serene one level ranch style centrally located in Milton, PEI. This very peaceful spacious property is close to many seasonal attractions such as Brackley Beach, Cavendish Beach, many golf courses, UPEI (MacLauchlan Arena), airport and other popular places within a short drive. Open concept with comfy seating, fully stocked kitchen, large back deck/yard space including a fire pit and a lovely front veranda to relax with a book and enjoy PEI sunsets.

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Guest favourite

A comfortable outdoor seating area features a spacious sectional sofa with neutral cushions. A dog is resting on the sofa. The wooden deck is partially covered with a patterned outdoor rug, and lush greenery surrounds the area, providing a serene atmosphere.

Home in Charlottetown

4.93 out of 5 average rating, 56 reviews

Modern, Spacious and Bright!

Book us for short term or long term stays! Perfect for vacationing and backyard entertaining, only 15 minutes to North Shore beaches. Close to Andrews hockey school and UPEI. Bright and spacious 3 bedroom, 2.5 bath ,1,500 square foot back-split home in the heart of Charlottetown. This home has a large master bedroom with en-suite and 2 large additional bedrooms. Parking included. Rental is for main level of home only. PEI Tourism License # 1201083

LocationFamilyBackyard

Top Guest favourite

An outdoor deck features a cozy seating arrangement with four black chairs surrounding a central fire pit. A table stands in the background, with expansive grassy hills visible beyond the deck. A clear blue sky provides a bright backdrop.

Home in North Wiltshire

4.98 out of 5 average rating, 46 reviews

Eco-friendly, 4-bedroom Passively Built Home

Experience the quintessential Island life with your family at our eco-friendly and sustainable home in Brookfield. Nestled on a grassy hill, our family home has everything you need for an ideal PEI vacation. You'll be just 20 minutes away from both Charlottetown, Summerside and stunning beaches. Our home was built with care and love, and is waiting to welcome you. It's conveniently located, making it easy to plan your visit and explore the island.

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Superhost

A modern cottage is depicted with large windows and a patio area. Red outdoor chairs are arranged around a circular table on a concrete patio, surrounded by neatly maintained grass and small trees. Additional cottages are visible in the background.

Cabin in Charlottetown

4.73 out of 5 average rating, 135 reviews

Brand New - Modern Cozy 1 Bedroom Cottage

Escape to comfort at Royalty Maples Motel & Cottages in Charlottetown. Our modern 1-bedroom cottages feature a private bedroom with Queen bed, full kitchen, bathroom, living area with sofa bed, Wi-Fi, smart TV, air conditioning, and free parking. Enjoy a quiet setting just minutes from downtown, beaches, golf, restaurants, shopping, and PEI attractions. Dog-friendly units available (max 1 pet). BBQ rentals available seasonally.

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Top Guest favourite

A two-story house with a distinctive blue exterior is presented. The structure features a central entrance with a covered porch, flanked by evenly spaced windows. A well-maintained lawn and neatly trimmed bushes surround the front, leading to a paved driveway that accommodates two vehicles.

Apartment in Stratford

4.94 out of 5 average rating, 196 reviews

Keppoch Sunshine

Welcome to our home where you can wake up with a view of the water! We offer a spacious (1000 sq feet), bright and comfortable one bedroom apartment with its own separate entrance and is the perfect mix of quietness, privacy and convenience. We are located on the Keppoch Road in Stratford within minutes of downtown Charlottetown and the airport. Our home can be your ‘home away from home’ to enjoy your Island stay.

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Top Guest favourite

A comfortable blue sofa with decorative pillows is positioned opposite a wooden coffee table. A painting of coastal cottages is displayed on the wall above the sofa, while soft light from a floor lamp and natural light from the window create a cozy atmosphere.

Bungalow in Oyster Bed Bridge

4.93 out of 5 average rating, 323 reviews

The Robin Cottage - Stargazing!

The Robin cottage is set back from the road with 3 other cottages. Fully equipped with all the extras! Our cottages are conveniently located in the populair north shore area. 20 min away from Charlottetown and Cavendish, and only 5 min away from Brackley Beach. Each tip of the island is easily reached within an 1.5 hours. This is the perfect place to gather your family for a get-a-way and to explore the island!

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