House holiday rentals in Bobcaygeon

4.99 out of 5 average rating, 222 reviews

A serene outdoor seating area is situated on a grassy slope, facing a tranquil expanse of Lake Ontario. White chairs are arranged in a circle around a fire pit, with a clear blue sky and distant shoreline enhancing the peaceful ambiance.

Home in Prince Edward

Fitzroy Lakehouse Waterfront Hot Tub

Fitzroy Lakehouse is a private waterfront bungalow on Lake Ontario with a year-round hot tub and direct water access. Enjoy lake views from the main living area and primary bedroom, plus a 200-foot private rock beach with seasonal stairs from Victoria Day to Thanksgiving. Minutes from Prince Edward County wineries and Consecon, with fast Starlink internet, dedicated workspace, firepit, kids play structure, and EV charger. Ideal for families, couples, and remote workers seeking privacy and views.

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.

4.99 out of 5 average rating, 248 reviews

Home in Corktown

Stylish 1870s Home near Distillery District & Old Toronto

Visiting for fifa? Stop here...Steps from the Distillery District downtown, this Top rated listing is a beautifully restored 1870s row-house (townhouse) that blends historic charm with modern refinement. Thoughtfully designed throughout, it’s located downtown also close to St. Lawrence Market, and some of the city’s best cafés and restaurants. In the evening, unwind in the serene, charcoal-toned bedroom beneath the warm glow of a statement chandelier—your refined Toronto retreat awaits

4.88 out of 5 average rating, 238 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

4.98 out of 5 average rating, 218 reviews

An exterior view of a modern black tiny house is depicted, surrounded by trees and natural foliage. Two sets of stairs lead to the entrance, with a gravel pathway visible. Window placements create a unique design, and soft lighting illuminates the scene against the evening sky.

Home in Gravenhurst

Woodland Muskoka Tiny House

Enjoy the sounds of nature when you stay in this unique tiny house. This 600 sq ft home is nestled amongst 10 acres of towering trees, granite rock and trails to explore. The tiny home will not feel so tiny once inside. With high ceilings, plenty of windows, and surprisingly spacious rooms - it is the perfect hideaway for those wanting to unplug in Muskoka. The three season, screened in porch invites you to enjoy your coffee (or wine!) in nature without being bothered by the mosquitos!

4.95 out of 5 average rating, 213 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 bright and inviting living area features large windows that offer views of the surrounding greenery and deck. Comfortable seating is arranged around a central coffee table, complemented by a patterned area rug. Soft lighting enhances the cozy atmosphere.

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.

4.97 out of 5 average rating, 328 reviews

An outdoor seating area features several dark wooden Adirondack chairs arranged in a circle around a stone fire pit. Soft glow from string lights adds warmth to the scene, while the modern cottage is visible in the background, nestled among tall trees.

Home in Huntsville

Wolegib Muskoka | Hot Tub | Beach | Swimming

Welcome to our private, modern Scandinavian-style cottage, set on 3 acres of pristine land with conservation property across the water, ensuring ultimate privacy and tranquility. The cottage boasts floor-to-ceiling windows that invite natural light and offer stunning views of the Muskoka River and surrounding nature. Just 40 steps from the front door, you'll find a private beach and dock, offering calm, clear waters perfect for swimming—ideal for families with children.

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, 107 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.

4.97 out of 5 average rating, 302 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, 107 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 Shanty Bay

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, 237 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

4.91 out of 5 average rating, 112 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 Rouge

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

A charming cottage is set amongst lush greenery, with a red wood exterior and light yellow trim. The front features a welcoming staircase leading to the entrance. A small storage area is visible on the side, complementing the natural landscape.

4.93 out of 5 average rating, 27 reviews

Charming 3-Bedroom Lake Front Cottage with Pool

A panoramic view of Sturgeon Lake showcases calm waters reflecting a clear blue sky. A wooden dock extends into the lake, with a paddleboard resting alongside. Lush green grass frames the scene, enhanced by vibrant foliage in the foreground.

4.75 out of 5 average rating, 24 reviews

The Birch Cottage

Weekly house rentals

4.97 out of 5 average rating, 71 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 private dock is shown extending into Sturgeon Lake, complemented by a spacious wooden deck. Four adirondack chairs are positioned along the edge, facing the water. Lush green grass surrounds the area, and a clear blue sky with fluffy clouds is visible above.

Home in Fenelon Falls

The Lake House in Fenelon Falls ~ Sturgeon Lake

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.

4.74 out of 5 average rating, 31 reviews

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

4.97 out of 5 average rating, 30 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!

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

Two red Adirondack chairs are positioned along a tranquil waterfront, facing a reflective expanse of water. Lush greenery and stone accents surround the scene, while boats are visible along the shore, creating a serene atmosphere for relaxation.

4.79 out of 5 average rating, 43 reviews

Tranquil waterfront getaway!

5 out of 5 average rating, 40 reviews

Home in Fenelon Falls

Lakefront Cottage Kawartha Lakes & Waterfront Dock

4.97 out of 5 average rating, 29 reviews

A circular firepit area is surrounded by red Adirondack chairs, set on a grassy bank by the tranquil lake. Trees frame the scene, reflecting softly on the water's surface. The hot tub and additional seating can be seen nearby, creating a welcoming outdoor space for relaxation.

Home in Ennismore

Waterfront Escape | Hot Tub, Sauna, Pet Friendly

Private house rentals

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.

4.94 out of 5 average rating, 36 reviews

Lakefront Bungalow "Sunrise Bay" Kawartha Lakes

4.97 out of 5 average rating, 34 reviews

A lakeside luxury retreat features a spacious exterior with a large deck and expansive yard. Lush green grass is surrounded by trees, and several outdoor seating areas, including a dining set and Muskoka chairs, are visible. A wooden dock extends into the calm waters of Lake Simcoe.

Home in Georgina

Royal Beach Lake House & Spa w/ Hot Tub & Sauna

5 out of 5 average rating, 4 reviews

Home in Baysville

Bay Dreamer

4.91 out of 5 average rating, 35 reviews

Home in Norland

River Pine Retreat

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!

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

5 out of 5 average rating, 3 reviews

A modern living area is highlighted by a neutral-toned sofa, complemented by two blue accent chairs. A wooden coffee table occupies the center space, while a flat-screen TV is mounted on the wall above a contemporary fireplace. Natural light fills the room through a large window.

Home in Cameron

Cottage #4 on Sturgeon Lake, Minnesota