Vacation rentals in Port Bolster

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Top-rated vacation rentals in Port Bolster

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Top guest favorite

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.

Home in Kawartha Lakes

Lakefront Bungalow "Sunrise Bay" Kawartha Lakes

As seen on "Scott's Vacation House Rules". Wake up to a beautiful sunrise at our peaceful all season lakeside retreat! Enjoy views of the lake from the dock, the screen room, the main bedroom and all areas of the main living area. Have fun outdoors on our large property with 120 ft of waterfront or enjoy our expansive indoor living area; featuring ample seating, a games room and a custom built vertical chess board. Watch the moon rise over the lake and stay warm by our large outdoor fire bowl.

FamilyLocationBiking

4.96 out of 5 average rating, 53 reviews

Top guest favorite

Home in Georgina

Water’s Edge

Welcome to Water’s Edge – Lake Simcoe, a cozy charming cottage retreat with private lake access just steps away via your own dock and boathouse. Enjoy peaceful days swimming, sunbathing, fishing, or relaxing on the rooftop seating area with stunning lake views. Inside, you’ll find a fully equipped kitchen, comfortable beds, high-speed Wi-Fi, and outdoor spaces with a BBQ, firepit, and plenty of room to unwind and enjoy nature. Perfect for couples, families, or friends seeking lakeside relaxation

LocationFamilyHospitality

5.0 out of 5 average rating, 35 reviews

Guest favorite

A covered patio area features a hot tub alongside a glass-topped table with comfortable seating. The peaceful lakeside view showcases expansive green space and a row of chairs positioned along the shore, framed by trees lining the property.

Cottage in Georgina

Sunset Shores Lakehouse- Hot Tub, Wet Bar & Games

Welcome to Sunset Shores Lakehouse! Nestled in a tranquil bay on the shores of Lake Simcoe, this spacious family lake house is the perfect escape in all 4 seasons with many indoor and outdoor activities to enjoy! This peaceful waterfront retreat boasts 4 bedrooms + Wet Bar + Patio Oasis with lakeside Fire Pit + 6 person Hot Tub overlooking the lake and spectacular daily sunsets and sunrises you wont want to miss! Only 1 hour from Toronto and close to many Georgina attractions and adventures!

LocationValueQuiet

4.96 out of 5 average rating, 106 reviews

Top guest favorite

The tiny home features a covered deck with a red umbrella, offering outdoor seating for relaxation. Lush green grass surrounds the structure, enhancing the sense of privacy. Large windows provide natural light, complementing the modern black exterior.

Tiny home in Beaverton

Riches Retreat-Tiny Home

Beautiful newly built Tiny Home on a large part of private property with its own driveway & parking. Very secluded with large yard in front, hosting many type of birds, squirrels and rabbits to watch. Perfect setting & space to have a peaceful, relaxing getaway. You'll have a feel of privacy & be comfortable. Great place to unwind, have fun or even catch up on work with no distractions! Well equipped kitchen for cooking & BBQ on deck. Parking for 3 vehicles plus space with a small/med trailer.

FamilyLocationIndoor spaces

4.99 out of 5 average rating, 149 reviews

Top guest favorite

A serene outdoor space is featured, illuminated by soft lights under a night sky. A patio area hosts a seating arrangement, surrounded by lush greenery and a fire pit. The water is visible in the background, enhancing the tranquil setting.

Cottage in Beaverton

Private Waterfront Cottage at Lake Simcoe

Luxurious and spacious private waterfront cottage at Lake Simcoe. Enjoy stunning lake and sunset views. An hour from Toronto, this newly renovated cottage offers a fully equipped kitchen, 5 bedrooms, 3 bathrooms, and a spacious dining and living area. Additionally, beautiful outdoor patio, BBQ grill and private fireplace, perfect for relaxing with friends and family. This cottage offers easy access to a private waterfront to enjoy water based activities such as swimming, boating, and fishing.

FamilyLocationWifi

4.99 out of 5 average rating, 92 reviews

Top guest favorite

Cottage in Georgina

Resort-Style Luxury Waterfront Cottage

Experience luxury at our 5-star, Superhost-rated waterfront cottage on Lake Simcoe, just 80 KM from Toronto! A guest favorite, it offers breathtaking sunsets and sunrises from the living room and loft. Relax on the sandy beach with waist-deep waters, and enjoy the patio, BBQ, bar, lounge, kayaking, and fishing. With a fully equipped kitchen, 3 bedrooms, and 2 bathrooms, it comfortably accommodates up to 8 guests. Book your dream getaway today for the perfect blend of relaxation and adventure!

ValueLocationBathroom

4.96 out of 5 average rating, 144 reviews

Superhost

The living room features large windows, offering a view of the lake. A spacious dark sofa is arranged around a coffee table, complemented by a side table with a lamp. Light-colored walls and wooden floors enhance the bright and open atmosphere.

Bungalow in Georgina

Lake Simcoe Retreat

Holiday retreat on Lake Simcoe with Sunset view. Front bedrooms and kitchen facing the river and Living room, Dining room, other rooms and open kitchen facing the Lake. You can enjoy the views from every part of the house. Totally renovated interior. High speed internet, a work space, Close to many world class family activities including Fishing, Hunting, Ice Fishing, Snowmobiling. Conveniently located an hour from Toronto, closest small town 5 minutes drive and Sutton town 12 minutes drive.

FamilyLocationAccess

4.81 out of 5 average rating, 128 reviews

Guest favorite

A spacious two-story home, characterized by a stone façade and large front windows that offer a stunning view of the sunset. The well-maintained lawn is adorned with neatly trimmed shrubs and flowers, leading to a welcoming entryway. The outdoor seating arrangement is visible, suggesting an inviting area for relaxation.

Cottage in Orillia

Lakefront Simcoe Cottage | Dock&Kayaks |Firepit

Escape to the shores of Lake Simcoe for a relaxing four-season getaway with family and friends. This 4-bedroom lakefront cottage sleeps up to 8 guests and offers beautiful water views, direct lake access, fishing, kayaks, a canoe, paddle board, and fire pit. Start your day with peaceful mornings by the water, spend the afternoon fishing , kayaking, paddling, or swimming in season, and unwind by the lake . Just a short drive from Downtown Orillia, Casino Rama, and year-round attractions. 😊

LocationFamilyOutdoor spaces

4.92 out of 5 average rating, 48 reviews

Guest favorite

A stone pathway leads to a fire pit surrounded by colorful Adirondack chairs in red and yellow. The view overlooks the lake, with a dock extending into the water under a clear blue sky, providing a serene setting for gatherings.

Home in Orillia

Waterfront Cottage Over-the-Water view w BBQ& Wifi

Our cottage backs directly onto lake Simcoe with a view overlooking the water reminiscent of a four season water villa bungalow. Enjoy the entire house with your family and friends and be captivated by nature's beauty as the sun sets behind the treeline across the lake. Easy access to lake Couchiching for fishing in the summer and ice fishing in the winter, 30 mins to Mount St. Louis for skiing and snowboarding, 30 mins to Vetta Nordic Spa and Casino Rama is only a 10 minute drive away!

LocationFamilyCheckout

4.83 out of 5 average rating, 320 reviews

Guest favorite

A spacious backyard features a fire pit surrounded by four adirondack chairs. The cottage showcases large windows and a deck with outdoor dining furniture and an umbrella. Two kayaks are stored nearby, adding to the lakefront atmosphere.

Home in Kawartha Lakes

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.

FamilyLocationOutdoor spaces

4.93 out of 5 average rating, 141 reviews

Superhost

An indoor heated pool area is featured, enclosed with high ceilings and large windows. Comfortable seating is arranged nearby, with a minimalist coffee table in the center. A garage-style door allows for an open transition to the outdoors, enhancing the spacious feel of the room.

Home in Beaverton

Luxury Family Home Indoor Pool Hot Tub Sauna

Relax and reconnect at this one-of-a-kind family getaway directly across from Lake Simcoe. Enjoy deeded lake access at the end of the road, stunning sunset walks along Thorah Beach, and plenty of space to play on the large private property. ✔ Heated indoor pool with retractable wall for indoor/outdoor living ✔ Hot tub & sauna ✔ Fire pit for cozy evenings under the stars ✔ Direct lake access nearby ✔ Large yard for family fun and games ✔ Beautiful sunset views and beach walks

FamilyValueLayout

4.84 out of 5 average rating, 77 reviews

Superhost

Cabin in Township Of Brock

Lake view house

Lake front home, come take a break and unwind at this peaceful location. Steps to the lake , with breathtaking views of the lake and magical Sunsets Private patio with view of the lake Loft bedroom with A/C unit Perfect for romantic getaways Condo kitchen, Natural Gas Bbq. Indoor full bathroom plus an outdoor showers too One hour north of Toronto. Parking on site. This is a lake house, the size of a condo. Full privacy, owner is not on site

LocationValueBathroom

4.7 out of 5 average rating, 23 reviews