Vacation rentals in Head of Hillsborough

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Top-rated vacation rentals in Head of Hillsborough

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Top guest favorite
An aerial view showcases the dome-shaped eco-dome nestled among snow-covered trees. The white geometry contrasts with the surrounding evergreen forest, while the roof's skylight is visible. A pathway leads to the dome, inviting guests to explore the natural winter landscape.
Home in Montague
4.95 out of 5 average rating, 176 reviews

Oceanfront Luxury Glamping Dome

Nestled in the woods of PEI’s south-eastern shore, and overlooking the Murray Islands is the Maytree Eco-Dome, a unique 26ft luxury accommodation complete with a kitchen, bathroom, private bedroom, and lounge with views of the water. Maytree offers direct access to your own private beach, and is the perfect location for kayaking, hiking, or having a beachside bonfire. Whether you are looking for a rejuvenating retreat, or an anchor for an Eastern PEI adventure. PEI Tourism License #1300747 Our all season eco-dome is complete with a modern kitchenette, full bathroom, jacuzzi, and other amenities needed for an enjoyable stay. Full access to the eco-dome, patio, and surrounding forest, with private beach access. My husband, Ken, and I and our son, Hugh, live on the property down at the end of Sunset Beach Rd. We are happy to help if you need anything during your stay. The preferred way of contact is through texting at the number provided. We're tucked away just a few kilometres outside of Murray River, a charming fishing village offering a variety of places to eat & views to discover. We recommend having a car while visiting Prince Edward Island. There is limited public transport available in Eastern PEI.

Guest favorite
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
4.88 out of 5 average rating, 176 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

Top guest favorite
A wooden deck is visible alongside the Cardigan river, featuring a hot tub and grill. A path made of pavers leads to the deck, framed by greenery and young trees, while a sign labeled 'The Owen' stands prominently.
Dome in Cardigan
4.99 out of 5 average rating, 176 reviews

Shoreline Retreat River front luxury geo-dome

Relax and enjoy the beautiful Cardigan river from the comfort of your own 2 bed, full kitchen & full bath luxury dome with private deck and hot tub and hammock . Wifi and smart TV included. Close to Confederation trails, liquor store, restaurants, golf courses and grocery stores. Beach access, clam digging etc ( water shoes recommended due to shells) Central fire pit to enjoy evening s’mores. Access to laundry facilities on site for weekly rentals. PEI tourism establishment licence # 1300740

Top guest favorite
An outdoor space is featured with a fire table, surrounded by comfortable seating. Glittering lights hang in the background, and a hot tub is visible nearby, highlighting an inviting atmosphere for relaxation.
Home in East Royalty
4.96 out of 5 average rating, 139 reviews

Jim’s Retreat w stone fireplace & 6 person 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.

Top guest favorite
A modern chef's kitchen features dark cabinetry with glass accents and a large island with four upholstered bar stools. A stainless steel gas stove, hood, and refrigerator are prominently displayed, alongside essential appliances, and a mix of natural and ambient lighting enhances the space.
Condo in Downtown Charlottetown
4.95 out of 5 average rating, 210 reviews

Downtown Luxury Award Winning Private Condo

Featured in PEI LIVING magazine, our historic 130 year old Thomas Alley House was completely renovated in 2018. Our suite is 1200sqft and features a full chef's kitchen complete with gas stove, 2 bedrooms and 2 bathrooms. Quartz throughout. The master bath has heated floors and his/her walk in glass shower. The 2nd bathroom features a full 6' soaker tub. Furniture is by LazyBoy. 2 fireplaces. Parking. This is "the" address in downtown Charlottetown. Tourism PEI license #1201041

Top guest favorite
A charming cabin nestled among trees is approached by a stone pathway. The surrounding greenery, featuring shrubs and tall trees, creates a serene environment. Soft sunlight filters through the leaves, illuminating the cabin's exterior, which is complemented by a tranquil natural setting.
Cabin in Belfast
4.99 out of 5 average rating, 142 reviews

Miracles on Polly - Memory Lane Cabin

Inspired by Mother Goose, or the figures one holds dear. A place for her to rest after a long fairy tale journey. A place to remember and cherish her mementos and treasures she has collected along the way. A cabin and space that embraces both creativity and comfort. Filled with antiques and refurbished furniture, pianos, and organs. This is our third cabin we have installed on our four acre property. There is an exclusive 6 person hot tub off the veranda and the sauna is only steps away.

Top guest favorite
A warm-toned exterior of a two-story guesthouse is showcased, featuring large windows and a balcony with red chairs. Lush green grass and wild vegetation surround the building, complementing the welcoming design and inviting presence amidst the natural landscape.
Guesthouse in Morell
5 out of 5 average rating, 21 reviews

Dune Vista Cottage

Exceptional views throughout; Bright natural light; soaring vaulted ceilings; sleeps up to six (6) people. The decks offer views of the sand dunes, ocean, and harbour or the gardens. The main level has a modern chef's kitchen, informal dining, two living areas with pullout sofa beds, one queen, and the other double. The full laundry and a bathroom with a shower are located on this level. The upper-level bedroom has a queen-sized bed, 38-inch TV, a loft and deck with panoramic ocean views.

Guest favorite
A bright living area features a comfortable couch, two accent chairs, and a mounted flatscreen television. Natural light floods in through large windows, offering views of the surrounding greenery. Soft curtains frame the windows, and side tables with lamps complete the cozy setting.
Cottage in Saint Peters Bay
4.98 out of 5 average rating, 108 reviews

Shacks Rentals - Open year round (Cottage #3 of 3)

Three Cabins on site - Search 'SHACKS RENTALS' to find all listings! Also, visit lumbershacks. com to find Airbnb links for all three cabins. This bright and cozy newly constructed cottage has everything you will need to enjoy a relaxing stay. The location is only a short walk from central St. Peter’s Bay and one of the most beautiful sections of the Confederation Trail. St. Peter’s not only has beautiful scenery and walking trails but is also home to local shops and delicious food!

Top guest favorite
The charming cottage exterior is clad in light wood shingles, with two large front windows framed by decorative shutters. A welcoming front porch features two black adirondack chairs and pink flower pots, complemented by a landscaped pathway leading to the entrance.
Home in Morell
4.94 out of 5 average rating, 18 reviews

Big Sea Beach House

July and August SUNDAY check in. Forget your worries in this comfortable and serene space. Brand new private 3 bedroom cottage, surrounded by trees in a oceanside subdivision in Morell. Listen to the ocean while sipping your morning coffee, stroll to a world class beach ( St. Peter's Harbour Rd Beach) and enjoy your vacation relaxing in our large screened sunroom. July and Aug Sunday check in 7 night min.. Off season 3 night min, and please contact to request preferred dates.

Top guest favorite
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
4.85 out of 5 average rating, 226 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.

Top guest favorite
A single-story cottage is situated on a spacious green lawn, surrounded by trees. A wooden deck with steps leads to the entrance. A fire pit is visible on the ground nearby, creating a welcoming outdoor space.
Cottage in Mount Stewart
4.95 out of 5 average rating, 64 reviews

Cheerful 1 Bedroom cottages with stunning views

This one bedroom cottage has everything you are looking for when you are vacationing on PEI. You are surrounded by beauty and nature everywhere you look. This will be your place to unwind and relax at the end of a long day exploring the Island. You will be five minutes away from the beautiful Dalvay beach. It is a short 10-15 minutes drive to amazing golf courses, and only 20 minutes way from Charlottetown. You will not be disappointed! Licence number # 2203275

Top guest favorite
A charming waterfront cottage is shown set against a clear blue sky. The exterior features a grey facade with a metal roof and a spacious wooden deck. Surrounding the cottage, a green lawn is dotted with trees, enhancing the natural setting.
Cottage in York
4.95 out of 5 average rating, 189 reviews

Steel Away (Cottage)

We now have a fully renovated, waterfront cottage available for weekend getaways or extended escapes. An open concept complete with a Queen bed and two twins bunks, kitchen, bathroom, deck and private hot tub. Located at the end of Queens Point on Tracadie Bay, guests can enjoy all the Island has to offer from our central location, or get away from it all and enjoy the Off Season star filled nights from the comfort of a hot tub.

Popular amenities for Head of Hillsborough vacation rentals