Vacation rentals in Winsloe South

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

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

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.*

Jim’s retreat stone fireplace/seasonal hot tub!

Just minutes to downtown restaurants and shopping and only 10 minutes to Brackley beach! Also Relax in this new luxurious home while you curl up by the fireplace with a book or enjoy the large back deck with fireplace table or have a relaxing soak in the duel jet hot tub. Please NOTE: Hot Tub seasonal (May 15 to November 15) This "Entire" private home includes a full kitchen, cooking utensils, pot and pans, linens, towels, luxury bathrobes, High Speed Internet, tea, coffee, spices and games.

Cozy Waterfront Cottage on Winter Bay, PEI

Your perfect PEI getaway! This cozy 2-bedroom cottage sits right on Winter Bay - just steps from the water for kayaking, and relaxing seaside days. Start your mornings with coffee overlooking the bay, soak in the peaceful surroundings, and unwind in a quiet family-friendly setting. Just a short 5-minute drive brings you to some of PEI’s most stunning shorelines. Whether you’re planning a family vacation or a beach-filled adventure, this is a place you’ll want to come back to year after year.

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.

Sunset Shadow

Modern yet cozy newly built home centrally located in the heart of PEI. Sunset Shadow offers three bedrooms and two bathrooms, providing comfortable accommodations for families, couples, or small groups. Just 12 km from Summerside, 25 km from Cavendish Beach, and 50 km from Charlottetown, you’ll be close to PEI’s most popular attractions. Perfect for beach trips, golf getaways, or peaceful escapes, with a serene setting beside our sister property, Sunset Hideaway.

Harbour View Haven

The search for the perfect summer escape is over! Come sit by the bonfire, and enjoy the ever-changing sunsets. Nestled on a quiet lane, Harbour View Haven is a beautiful summer home with a stunning water view of the Charlottetown Harbour. With 5 luxurious bedrooms and 6 bathrooms, it provides sleeping space for a total of 14 guests. The space has been thoughtfully designed with a fully equipped kitchen and panoramic view within an open concept living space.

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.

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.

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

The Averim | Close to Brackley beach

Tucked back from Rustico Road, our fully equipped cottage is the perfect PEI home base. Just minutes from Brackley Beach and the National Park, we provide all the extras for a seamless stay. Located in the popular Green Gables Shore area, you’re only 20 minutes from Cavendish and Charlottetown. Centrally situated, you can reach both East Point and West Point in under two hours.