Holiday houses in Bailieboro

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Top-rated holiday rentals in Bailieboro

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

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Top Guest favourite

A stylish living area features deep green walls adorned with framed artwork. A plush velvet sofa and leather armchair provide cozy seating around a wooden dining table. A vintage chandelier hangs from the ceiling, while a decorative fireplace adds character to the space.

Condo in Port Hope

5 out of 5 average rating, 257 reviews

The Wilf Jones – Heritage Loft, Downtown & Hot Tub

The Wilf Jones, the most central airbnb in Port Hope! This main street stay is the optimal location for a morning walk to the coffee shop, unique eateries, and evening cocktails. To see more, visit: @thewilfjones PLEASE NOTE There are two stair cases from street level to the apartment. Expect some noise transfer from other travellers at times. While the hot tub itself is only available to you, the patio has a shared privacy wall with the neighbouring unit (there is a second fully private patio).

ValueFamilyWi-Fi

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.

LocationFamilyDecor

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, 258 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.

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Top Guest favourite

Cottage in Cobourg

4.98 out of 5 average rating, 365 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.

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Top Guest favourite

A scenic view depicts a house positioned near a rocky shoreline. Trees line the area, while gentle waves lap against the shore under a partly cloudy sky. The space conveys a serene environment surrounded by nature.

Home in Cobourg

4.96 out of 5 average rating, 108 reviews

Marigold Mansion Lakeside

Marigold Mansion Lakeside - Luxury Retreat -Concierge Stays, Spa Access. Not just a place to stay, a curated lakeside experience designed for connection, comfort, and effortless luxury. Perfect for romantic getaways, family stays, Girls Weekend, Work from lakeside week or health recovery stays. Beautiful lake views, close to the beach, waterfront trails, a world renowned spa, boutique shopping and dining. Once a barn in the 1800’s renovated in 2022/23 into a uniquely stylish retreat.

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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.

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Superhost

Home in Otonabee-South Monaghan

4.87 out of 5 average rating, 15 reviews

Little blue lake house

Beautiful waterfront lake house on Rice Lake accessible year round by a paved road, 1 hr from Toronto. Private deck, large yard, lots of shoreline. Fire pit, excellent fishing, quiet. Fall asleep to the sound of the waves, fish right off the dock (May 15th-Oct 1st). Shower in fresh spring water from our on-site artesian spring. Two Kayaks are available BBQ grill available for guest use (Propane isn't included, but we try to keep the tanks reasonably full) StackTV(HBO Max) and 55" HD TV

LocationFamilyCleanliness

Superhost

A private verandah displays two lounge chairs facing a table, surrounded by potted plants. Textured baskets and a soft throw add warmth, while decorative railings frame the area. The open sky and greenery in the background enhance the serene outdoor space.

Home in Port Hope

4.87 out of 5 average rating, 235 reviews

1840 Keyhole - HOT-TUB BEACH Historic Port Hope

1840's Dorset House - LUXE 1-bed + living & kitchen, private hot-tub terrace & verandah, AC, roaring fire, lux bedding, original art, & eclectic living. Guide-book shares all + KEYHOLE treasure hunt - LUSH garden - WALK to secret beaches, dining/drinks, coffee, market, vintage, galleries, lake & river trails: for golf - bike or butter tart tour, or a romantic break... Find big skies, clean air & soft breezes... exactly what you are looking for! Breathe & STAY a while...

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Superhost

Dome in Port Perry

4.9 out of 5 average rating, 588 reviews

North Geodome - Birchwood Luxury Camping

Located one hour from Toronto, Birchwood is a luxury camping experience for two. Immersed in a private forest on Scugog Island, our geodesic dome allows for a cozy and relaxing getaway. Enjoy the surrounding landscape and check out local shops and restaurants on Port Perry main street. Our geodome is designed for 2 guests however a group 3 adults are welcome. Additional guests must be 12+ and added to your reservation at the time of booking. We do not allow pets.

LocationValueBarbecue

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, 140 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.

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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.

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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.

ValueFamilyHot tub