Holiday houses in Bailieboro

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Top-rated holiday rentals in Bailieboro

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Top Guest favourite
Guest suite in Grafton
5.0 out of 5 average rating, 155 reviews

The Eh Frame - Nordic Spa Retreat - Daybreak Suite

The Eh Frame is a 3-story, Scandinavian-inspired luxury cabin with two fully separate units: the Sunrise and Sunset Suites. Your group will have exclusive access to the Sunrise Suite (everything shown in the photos), including two bedrooms, a patio, a private spa, and a fire pit. The front unit, Sunset Suite, is a separate rental. A full firewall runs through the center of the home, ensuring privacy and comfort for all guests. Located just minutes away from Whispering Springs and Ste. Annes Spa.

Top Guest favourite
Cottage in Trent Lakes
4.99 out of 5 average rating, 166 reviews

Panoramic Lake Views Inside & Out, Cozy & Relaxing

Enjoy panoramic views of Lower Buckhorn Lake with the family! Relax perched in the hot tub atop the rocks of the Canadian Shield, nestled among the tall pines. This newly updated waterfront cottage features 3 bedrooms & an open concept living space. Over 280 feet of waterfront for you to enjoy the sunrise & sunsets & fish off the dock! Get cozy on the couch, play games, or watch movies. Take a stroll around the island. Hi speed Wi-fi to work or play. 6 minutes to town, less than 2 hrs from GTA.

Top Guest favourite
An outdoor stone wall shower is positioned next to a wooden deck, leading to a private pond. The deck features a covered area with dining furniture. Lush greenery surrounds the space, and sunlight illuminates the scene under a clear blue sky.
Shipping container in Clarington
4.98 out of 5 average rating, 117 reviews

Rustic Ridge

Rustic Ridge Tiny Cabin - Cozy Escape on Private Pond **Cabin will have to be winterized when temperature drops meaning no running water and outdoor shower, jugs of water will be supplied to rinse after sauna, bottled water in dispenser also provided.*** Welcome to Rustic Ridge Tiny Cabin, a unique shipping container retreat on the back of our property. Nestled by a private pond with a fountain, this serene cabin is the perfect escape for nature lovers and those looking to unwind in comfort.

Top Guest favourite
A spacious deck is shown with a wooden table and several chairs, offering a scenic view of the surrounding landscape. A barbecue grill is positioned near double glass doors that open to the interior. The setting is complemented by the gentle curve of the horizon.
Farm stay in Campbellcroft
4.99 out of 5 average rating, 255 reviews

Ganaraska Forest Getaway

Reconnect with nature at this unforgettable escape. Come and explore the Ganaraska Forest, Farm Life and Relaxation. Go mountain biking, hiking or head to Rice Lake and go fishing and boating. Enjoy living on a horse farm in the rolling hills of Northumberland County. Tour Prince Edward County for a Wine Tour. Enjoy Historic Port Hope. Go to the Cobourg Beach. Minutes from Canadian Tire Motorsport. Room to park your trailers. In the Winter ski Brimacombe or Snow Shoe on our private trails.

Top Guest favourite
Cottage in Cobourg
4.98 out of 5 average rating, 363 reviews

Couples Forest Retreat: Hot Tub, Sauna, Fireplace

Escape to a historic estate wellness retreat. Described by Narcity Canada as “Like Living in the Holiday” Praised as a couple's getaway, near Ste. Anne's Spa. Follow us @coachhouse_cobourg Step into a 150-year-old coach house nestled on a stunning 5-acre Victorian estate. This beautifully restored guest house combines historic charm with modern comforts, offering a private hot tub, sauna, a cozy fireplace, and a serene escape minutes from Cobourg’s vibrant downtown and pristine beaches.

Top Guest favourite
The tiny house cabin features a rustic wooden exterior, nestled among trees. A raised deck with a small table and chairs is visible at the entrance, inviting guests to enjoy the surrounding forest. Large windows allow natural light to fill the space.
Tiny home in Millbrook
4.99 out of 5 average rating, 105 reviews

Pinecrest Forest Cabin

Relax in the solitude of the forest and the luxury of a fully-equipped tiny house that sits in a forest connected to trails on conservation lands. Reconnect with each other or yourself during quiet days among the trees and peaceful nights under the stars. Recharge with nature at this unforgettable forest escape from the city. Cyclists, hikers and skiers appreciate the beauty of Millbrook Valley trails accessed directly from the property. Water lovers visit nearby beaches rivers, lakes.

Guest favourite
A vibrant red flower arrangement fills the frame, showcasing numerous blooms. An old-fashioned watering can is positioned slightly to the side, made of metal with a timeworn finish, suggesting a cozy garden setting.
Home in Port Hope
4.94 out of 5 average rating, 306 reviews

1890's COACH-HOUSE - Beach-Shop-DIne - LUX Retreat

GRAB summer! 1890 luxe COACH-HOUSE - lofty private retreat space on a treed lane, lush garden+terraces+hot tub. Airy, south-facing, vaulted, French doors, gourmet kitchen, sumptuous linens, roaring fire, edgy art, bespoke furniture, firepit, AC. Guidebook shares all - WALK to secret beaches, fab food/drink, funky vintage, river trails, theatre, hiking, biking, golf, butter tarts...work or romantic break EXACTLY what's needed - Big skies & soft breezes STAY A while...

Guest favourite
The geodesic dome features a modern white exterior, set against a backdrop of trees. A wooden deck extends from the dome, leading to a covered gazebo, with a pathway of wood chips guiding the approach. Soft sunlight filters through the branches, creating a serene atmosphere.
Dome in Uxbridge
4.86 out of 5 average rating, 138 reviews

The Bubble Glamping Dome

Escape to a luxury geodesic dome on our scenic farm, nestled at the edge of the forest. Fully equipped with heating, cooling, a private washroom, deck, and hot tub, it’s the perfect blend of comfort and nature. Explore the farm, meet our sheep, chickens, and livestock guardian dog, or hike over 100 acres of connected regional forest. Whether you’re relaxing under the stars or adventuring outdoors, this unique glamping retreat promises an unforgettable experience.

Top Guest favourite
A comfortable hammock is positioned beneath a large, shaded canopy on a wooden deck, offering a serene view of the lush landscape. The horizon is visible with a rolling green expanse, complementing the clear blue sky.
Tiny home in Cavan
4.98 out of 5 average rating, 107 reviews

The Little Hilltop Bunkie

Stay off-grid in an Amish built bunkie on top of a hill with the best south facing view in the area! Disconnect from your busy life and enjoy the country side. There is no wifi but cellular reception is good depending on your provider. There is an outhouse with compost toilet near the bunkie. There is no shower or sink. Enjoy the country and let nature do that talking! Pets are very welcome! Enjoy the trails and walk your dog(s) off leash.

Top Guest favourite
A bright living room features large windows that allow natural light to fill the space. Modern furniture includes a dark coffee table and comfortable seating with red armchairs. A decorative plant and a small lamp add to the welcoming atmosphere. Wooden flooring complements the neutral walls.
Farm stay in Cavan
4.96 out of 5 average rating, 155 reviews

Cielo Farm, a home with a view

Cielo Farm is situated high on the picturesque hills of Cavan, Ontario. It is a small working farm with a market garden, laying hens, Muscovy ducks, Nigerian Dwarf dairy goats and two beloved horses. If you are looking for rest relaxation and connecting with nature, this is a perfect location. We are close to Peterborough and several charming small towns and interesting excursions. You can be as quiet or as active as you wish.

Top Guest favourite
Cottage in Bailieboro
4.91 out of 5 average rating, 123 reviews

Majestic Lake Haven ~ Heated Pool~Hot Tub~ Fishing

Like something out of a storybook, this 6-bedroom lakefront retreat offers luxury and total privacy. Set on a sprawling lawn, it features a heated pool, hot tub, private dock for swimming or fishing, plus a BBQ and fireplace for cozy nights under the stars. Inside, you’ll find 1,800 sq. ft. of stylish space with a 52” smart TV, Yard Games, and board games—perfect for relaxing and making memories together.

Guest favourite
A bright and airy interior of the tiny home features high ceilings and large windows. The living area is furnished with a yellow chair and a coffee table, while a television hangs on the wall. An open kitchen area includes a refrigerator and counter space.
Tiny home in Peterborough
4.98 out of 5 average rating, 122 reviews

Tiny House Haven

This memorable place is anything but ordinary. A fully equipped Tiny Home nestled in a quiet area of Peterborough. Beautiful high ceilings and windows. We are the first Tiny Home in Peterborough and in the Spring and Summer the Magnolia trees and crabapple trees fill the view. With an outdoor fire area as well as an outdoor BBQ and eating area, this private and quiet spot is indeed one of a kind.

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