House holiday rentals in Bobcaygeon

4.89 out of 5 average rating, 104 reviews

A warm and inviting living area features wooden walls with large windows offering ample natural light. A spacious couch and two armchairs surround a glass coffee table on a soft area rug. A dining table is visible in the background, illuminated by natural light.

Home in Buckhorn

Lakefront Log Home-Reach Out for Special Deals!

Enjoy the ultimate lakeside escape at our stunning cottage on Big Bald Lake, just a 2-hour drive from Toronto! With 6 bedrooms and 2.5 baths, it sleeps 10 guests, making it perfect for families and friends. Enjoy direct lake access and embrace the serenity of the lake while kayaking or paddling in our 3 kayaks or paddle boat. Unwind in the sauna, work remotely, or simply relax on the sandy beach, ideal for kids and adults alike. To top it off, our charming gazebo offers breathtaking lake views.

4.98 out of 5 average rating, 228 reviews

An A-frame house is presented with a blue exterior amidst a snowy landscape. The structure showcases a sloped roof with multiple windows and a door leading to a deck. Surrounding trees, partially covered in snow, create a serene and natural setting.

Home in HUNT

Modern & Charming Eh-Frame | 4-Season Chalet

Escape the everyday chaos and unwind in this romantic A-frame home. Nestled on 36 acres of forest and marshland, this charming getaway will fulfill any couple’s desire for a private weekend in the woods to indulge in a deep connection with each other and with nature. High loft ceilings, exposed beams, wood burning fireplace, a cozy loft bedroom, spacious shower for two, and sunken soaker bathtub create an intimate and pleasing ambiance for your carefree retreat. Hosts an abundance of wildlife.

4.94 out of 5 average rating, 299 reviews

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

1890 COACH-HOUSE - Beach-Shop-DIne - POSH 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. Guidebook shares all - WALK to secret beaches, fab food/drink, funky vintage, river trails, theatre, hiking, biking, golf, butter tarts...work or romantic break Find big skies, clean air & soft breezes - EXACTLY what you are looking for STAY A while...

4.88 out of 5 average rating, 240 reviews

An aerial view captures a two-story cabin surrounded by vibrant autumn foliage. The landscape is adorned with various shades of orange, yellow, and green, showcasing the natural beauty of the wooded area. The winding path leading to the cabin is lined with scattered rocks and red outdoor chairs.

Home in Bobcaygeon

52 Acre Luxury Cabin - Hot Tub, Firepit & Trails

Our 2-bedroom cabin is the ultimate getaway for relaxation or embarking on new adventures. Situated within a serene 52-acre wooded property, our cabin offers exclusive access to 2 kilometers of private trails that connect to the Twin Lakes snowmobile trails. On our outdoor patio, you'll find a year-round hot tub, BBQ, and fire pit, all overlooking a tranquil seasonal creek. Despite its secluded location, we are a mere 10-minute drive from the charming boutiques and restaurants of Bobcaygeon.

4.95 out of 5 average rating, 126 reviews

Home in Prince Edward

SunriseSunsetPeace

Come for the sunrise, stay for the sunset! Total number of guests allowed 10 Additional guest must be under 10 years of age This luxury home has heated flooring and comes with a 7 seater 48 jet hot tub! This is a spacious home with ample sleeping arrangements. Ask host for more details. This home features a master bedroom with an ensuite located on the first floor. The master suite provides privacy, space and convenience. Perfect for our elderly guest or guest with limited mobility.

4.95 out of 5 average rating, 214 reviews

A modern two-storey home features a sleek design with large glass windows and balconies. The outdoor area includes a spacious deck with seating arrangements, while a decorative neon sign reads 'Water's Edge' against a textured green wall, enhancing the contemporary aesthetic.

Home in Belleville

Spectacular Waterfront Home in PEC

Situated on the edge of the beautiful Bay of Quinte, this brand new modern build is sure to steal your breath. Built in 2023, this stunning two-storey waterfront oasis, Water’s Edge, is located just over the Bay Bridge in spectacular Prince Edward County. Featuring two kayaks, fishing gear, outdoor propane fire table, and an upper and lower deck with front row seats to the most unforgettable sunsets. Water’s Edge is conveniently located to both Belleville and all that PEC has to offer.

4.94 out of 5 average rating, 266 reviews

A spacious grassy lot features six outdoor chairs arranged in front of a large deck. Sunlight filters through the trees, illuminating the cottage in the background. The deck is elevated, overlooking the yard, providing a serene space for relaxation.

Home in Selwyn

Gorgeous Pigeon Lake 4 season cottage

Very clean bright, newly renovated 3 BR cottage on Pigeon Lake, situated in Gannons Narrows, 90 min from TO. Very private and large, level grassy lot, great for kids.Great beds, premium kitchen, gas fireplace, paddle boat, canoe, large dock with boat ramp next door at the marina, wading for kids. Swimming, fishing, biking, hiking, 8 golf courses, fire pit with amazing sunsets, available for Christmas, New Year's & summer holidays. July- Aug there is a 7 night min stay, Fri to Fri.

4.93 out of 5 average rating, 120 reviews

Home in Little Britain

Cozy Lakeside Cottage on Lake Scugog

WELCOME TO OUR COZY ALL SEASONS COTTAGE! Private lakefront cottage (north shore of Lake Scugog) 2 bedrooms (1 queen, 1 full/double), 2 bathrooms, large bright sunroom with sleeper sectional. Large newly renovated deck. Beautiful lake view, large private dock, water facing deck with bbq, huge yard for games, bon fires and more. Located approx. 1.5 hours from Toronto, this cottage is the perfect place for couples, families or friends to escape the hustle and bustle, relax and unwind.

4.99 out of 5 average rating, 181 reviews

The serene backyard features a heated saltwater pool surrounded by a stone deck, bordered by lush greenery and blooming trees. A patio area includes outdoor seating and a grill, while large windows overlook the pool, enhancing natural light in the adjacent indoor space.

Home in The Beaches

Luxury 4BR: 365 Days Open- Heated Pool & Hot Tub

A Private Luxury Getaway in Toronto’s Most Coveted Neighbourhood Escape to an extraordinary 4-bedroom luxury home in Toronto’s iconic Beaches, where sophisticated design meets relaxed lakeside living. This top 1% rated Airbnb property offers an unforgettable weekend experience—perfect for families, couples, or a curated group of friends seeking both comfort and wow-factor. A year round private heated pool and hot tub are yours to enjoy !

A modern cottage is set on a green grassy area, featuring a spacious outdoor deck. The structure includes a screened sunroom, and seating areas with chairs and lounge furniture. A bright red star adorns the exterior wall, surrounded by trees and natural scenery.

4.94 out of 5 average rating, 108 reviews

Dock on the Bay

Enjoy your stay at our modern, bright, spacious 4 season cottage on Sturgeon Lake. Come stay for a winter or summer getaway This is the first time this gem has been listed for rent. On an inlet that goes directly out on to sturgeon Lake, this 3 bedroom, 1 bathroom cottage, is situated just minutes from the Victoria Rail Trail, perfect for snowmobiling, ATVing, hiking and biking. For snowmobiling, you can jump on the 310 or E108 OFSC Trail.

4.95 out of 5 average rating, 384 reviews

The exterior of the guest house showcases a modern wooden facade, accented by large windows. Soft outdoor lighting highlights the space, and a white bench is situated near a garden of wildflowers, creating a calm, inviting environment.

Home in Consecon

Hygge House, Cozy Boutique Guest House

Maximum 2 adults and up to 2 children (aged 9 and under). Inspired by the Danish word "Hygge", this little guest house is cozy, modern, and has everything you need for a quiet and peaceful getaway in the County. Nestled in rural Consecon, you'll get to unwind and recharge, all the while being just minutes away from grabbing a coffee, heading to the beach, or winery hopping in Hillier. Licence number ST-2019-0349 R2

4.97 out of 5 average rating, 304 reviews

The charming exterior of a converted church is presented, showcasing a striking red brick facade and a steeply pitched roof. Tall trees and lush greenery surround the building, adding to the serene setting. A welcoming entrance with a dark door and steps leads to the front.

Home in Prince Edward

The Prince Edward County Church, A Unique Escape

Stunning 1888 converted church in Prince Edward County on a private 2.3-acre waterfront property backing onto the Bay of Quinte. This one-of-a-kind stay blends soaring ceilings and historic charm with modern luxury. Sleeps 8 adults with 4 bedrooms, lake views, direct waterfront access, high-speed WiFi, Sonos, fireplaces, kayaks, and more. Featured in Forbes, House & Home & Cottage Life with over 300 guest reviews.

Popular amenities for house rentals in Bobcaygeon

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.88 out of 5 average rating, 108 reviews

A modern living area is highlighted by a sleek, electric fireplace beneath a large flat-screen TV. A rustic accent wall features wooden panels and decorative art. A comfortable gray sofa and a table set for dining complete the welcoming space, complemented by blue and natural tones.

Home in Innisfil

2 Bd Boardwalk Condo Patio Oasis

4.86 out of 5 average rating, 115 reviews

A bright and spacious living area features a comfortable white sofa paired with dark blue accent chairs. A stylish dining table is set for meals, while a gas fireplace and mounted television create a cozy atmosphere. Natural light fills the room through large windows.

Home in Horseshoe Valley

King Bed, Pool, Gym, Ravine View, Your Getaway!

4.92 out of 5 average rating, 132 reviews

The entrance features double doors in a dark finish, adorned with elegant seasonal wreaths. Flanking the doors are decorative wall art pieces. A small bistro table with two chairs is positioned on a stone patio, complemented by potted snake plants and decorative pumpkins.

Home in Barrie

Luxurious 4BDRM-King Bed-Barrie-near Snow Resorts

4.94 out of 5 average rating, 239 reviews

A private hot tub is positioned on a wooden deck beneath a lattice covering, allowing for relaxed soaking. Lounge chairs are arranged nearby, and vibrant greenery and decorative flowers provide a natural backdrop. A swimming pool can be seen in the distance, enhancing the outdoor ambiance.

Home in Port Perry

Home away from home with a hot tub and pool

4.94 out of 5 average rating, 205 reviews

Home in Prince Edward

Dragonfield House: a beautiful stay in central PEC

4.91 out of 5 average rating, 114 reviews

A bright sunroom is showcased with a glass ceiling and walls, providing expansive views of the surrounding nature. A glass dining table is surrounded by black chairs, resting on a soft area rug. The space offers a connection to the outdoors while remaining sheltered.

Home in Scarborough

Ravine Paradise ! heated pool and hot tub!

4.87 out of 5 average rating, 70 reviews

A hot tub is positioned on a wooden deck, offering a view of expansive greenery and Rice Lake in the background. Lush greenery and blooming white flowers frame the scene, and the sky above is clear with soft clouds, enhancing the serene outdoor setting.

Home in Gores Landing

Oriole Ridge Retreat, Hot Tub, King Suite

4.87 out of 5 average rating, 101 reviews

A hot tub is situated under a wooden gazebo, featuring railings and a ceiling adorned with decorative elements. Sunlight illuminates the scene, highlighting the inviting water surface. A view of the snowy landscape and frozen lake extends in the background, enhancing the serene atmosphere.

Home in Elmvale

Ski, Swim, Soak, Boat & Golf

Weekly house rentals

An aerial view displays a serene cottage surrounded by lush greenery. The structure features a green roof and a spacious deck leading to a wooden dock on calm waters. Natural stone accents blend harmoniously with the landscape, enhancing the secluded atmosphere.

4.95 out of 5 average rating, 59 reviews

Panoramic Lakefront Cottage

5 out of 5 average rating, 36 reviews

A stone pathway leads down steps towards a spacious lakeside yard. To the left, a grill is positioned for convenient outdoor cooking. Lounge chairs are arranged beside the water, surrounded by trees, creating a peaceful atmosphere. The lake glistens in the distance, under a clear sky.

Home in Bobcaygeon

Gorgeous Lakeside*weedfree*boat dock*hottub

4.88 out of 5 average rating, 17 reviews

Home in Fenelon Falls

The Lake House in Fenelon Falls ~ Sturgeon Lake

4.97 out of 5 average rating, 73 reviews

A comfortable living area is visible with a cozy armchair and a sectional sofa featuring beige upholstery. Natural light streams through large windows, offering a view of greenery outside. A stylish area rug and a decorative blanket add warmth to the hardwood floor.

Home in Lindsay

3 Bedroom House Rental

4.88 out of 5 average rating, 17 reviews

A serene lakeside fire pit area features several outdoor chairs arranged around a central fire. Soft hues of sunset illuminate the beach, enhancing the calm atmosphere. The surrounding landscape includes a pebbled shore and lush greenery, creating a peaceful setting for gatherings.

Home in Port Hope

Escape to the private shores of Lake Ontario!

4.97 out of 5 average rating, 31 reviews

The exterior of a welcoming cottage is presented, featuring a red facade with stone accents. A spacious porch is adorned with planters, inviting seating, and a prominent sign saying 'HELLO.' Lush green grass surrounds the structure, completing the peaceful setting.

Home in Fenelon Falls

The Little Red Cottage - Ideal for long stays!

Home in Dysart and Others

5 out of 5 average rating, 4 reviews

Designer A-Frame | Percy Lake + Cube Sauna

4.93 out of 5 average rating, 45 reviews

A serene lake at dusk reflects soft hues of orange and pink in the sky. The calm water mirrors the colorful clouds, while silhouettes of trees frame the scene, enhancing the natural beauty of the landscape.

Home in North Kawartha

Julian Lake Cottage

Private house rentals

5 out of 5 average rating, 19 reviews

Home in Huntsville

Muskoka Waterfront Cottage | Canoes, FirePit & BBQ

The image captures a private lakeside setting during sunrise. Adirondack chairs surround a fire bowl on a circular stone area. A private dock extends into the calm lake, reflecting the soft hues of morning light. Lush greenery frames the scene, enhancing the tranquility.

4.95 out of 5 average rating, 39 reviews

Lakefront Bungalow "Sunrise Bay" Kawartha Lakes

4.94 out of 5 average rating, 48 reviews

The exterior of a lakeside cottage is shown, featuring a large wooden deck and a covered seating area. Surrounding foliage includes tall trees reflected in the water, which mirrors the clear blue sky. Direct access to the shoreline enhances its tranquil setting.

Home in Peterborough

Kawartha Lakes , Chemong lake front property

5 out of 5 average rating, 4 reviews

Home in Baysville

Bay Dreamer

A shaded gazebo structure is situated on a wooden dock overlooking the water. It features wicker seating with colorful cushions, providing a comfortable space for relaxation. Towering trees frame the tranquil view, ensuring privacy and a serene atmosphere.

4.75 out of 5 average rating, 32 reviews

Waterfront*Hot Tub*Fire Pit*Wi-Fi*Screened Porch

A hot tub is positioned in the foreground, featuring bubbling water. A fire pit with flames is surrounded by four foldable chairs on the grass, offering a peaceful view of the waterfront and the autumn foliage in the background.

4.85 out of 5 average rating, 33 reviews

Waterfront Cottages Surrounded by Nature

4.92 out of 5 average rating, 90 reviews

A wooden deck is framed by tall pine trees, offering a serene view of Gold Lake. The calm water reflects the blue sky and surrounding foliage. Outdoor seating arrangements are positioned for relaxation, while shadows from the trees create a natural pattern on the deck's surface.

Home in Trent Lakes

Private Cottage on Clean Lake

A modern two-story cottage is showcased with a combination of stone and wood siding. Large windows allow natural light to fill the space. A clean, paved walkway leads to the entrance, surrounded by newly landscaped greenery, including shrubs and small trees.