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, 210 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

Tiny home in Crapaud

5 out of 5 average rating, 8 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

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, 82 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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Top Guest favourite

The modern exterior of a two-story home is showcased with a combination of white and wood paneling. Large windows span the upper level, while two garage doors are visible on the ground floor. The home is set against a clear blue sky and expansive green fields.

Home in Kensington

4.98 out of 5 average rating, 109 reviews

Sunset Hideaway

Modern but modest newly built home, located centrally in the heart of PEI. Two bedroom, one bathroom, sleeps six very comfortably due to large sectional and/or air mattress provided. 12 kilometres from Summerside, 25 kilometres from Cavendish beach and 50 kilometres from Charlottetown. Whether you are traveling or visiting with family and friends, looking to explore the beaches, needing a peaceful stay-cation or planning a golfing trip. This is a perfect location for your vacation needs.

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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, 98 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

4.86 out of 5 average rating, 264 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 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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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, 47 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, 136 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 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

4.94 out of 5 average rating, 324 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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Top Guest favourite

A view from the upper level showcases warm pine walls and cathedral ceilings with skylights. The open area below features large windows, allowing natural light to fill the space. A wooden railing provides a clear separation from the living area, enhancing the cozy atmosphere.

Cottage in York

4.97 out of 5 average rating, 164 reviews

WALK to beach - charming cottage in Stanhope

Situated on a quiet private lot -a 10 min walk to the beach, our spacious, air conditioned 3 BR cottage with cathedral ceilings is a place to relax & unwind. All comforts of home with nature as well Stanhope offers: - sandy beach - golfing - fishing wharf - walking & biking trails We are 25 min drive to Charlottetown Tourism PEI - License # 2200387 & also a member of Canada Select

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Top Guest favourite

The cozy sleeping area features a queen-sized bed with a decorative blue and white throw pillow. Soft lighting is provided by bedside lamps on each side. A small microwave is positioned on a nightstand, and a refrigerator is visible in the background.

Guesthouse in Charlottetown

4.98 out of 5 average rating, 132 reviews

A Country Home Inn the City - Cottage

The cottage is a self contained guest house is quaint, rustic cute with a queen sized bed, full kitchen, table, chairs, and full bathroom. On location with our four room inn, this cottage has access to the 2.5 acre yard with volleyball, basketball and soccer nets. Located five minutes from Royalty Crossing Mall and close to grocery stores and shops in Charlottetown.

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