Holiday houses in Port Bolster

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.

Family · Location · Air conditioning

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

Value · Location · Outdoor spaces

Waterfront Cottage-Sauna, Dock, 4-bed, 4 Parking

Bright and airy waterfront cottage in one of Lake Simcoe’s most desirable areas. The open-concept layout and unique lot design offer stunning lake views from almost every room. Enjoy custom furnishings, stylish decor, and a fully equipped kitchen—perfect for relaxing getaways or extended stays. Whether you're here for a peaceful retreat or lakeside fun, this cottage provides comfort, beauty, and convenience in a serene upscale setting. Ask us about fun activities that Lake Simcoe offers.

Family · Location · Parks

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.

Family · Location · Laundry

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.

Value · Location · Access

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!

Location · Family · Quiet

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.

Family · Location · Accuracy

Lakefront | Hot Tub, Private Dock & Sandy Beach

Luxury lakefront cottage on Lake Simcoe with a rare shallow sandy-bottom shoreline, private dock, and hot tub—perfect for swimming and family fun. Enjoy breathtaking sunsets, kayaking, paddleboarding, fishing, BBQs, and a fire pit. Ideal for family vacations, holiday getaways, and group retreats near Toronto, minutes from Hwy 404. Features 6 bedrooms, 4 bathrooms, a fully equipped kitchen, and an open-concept living area. Private, peaceful, and perfect for unforgettable memories year-round.

Value · Location · Accuracy

Upscale Spa w/ Hot Tub-Private Sauna-Penthouse

Welcome to our most Dramatic & Romantic Penthouse Spa Getaway Suite! Reconnect with your loved one or celebrate that special milestone in our professionally designed to play with all your senses spa suite, this escape will leave you feeling refreshed and rejuvenated! Cozy up to any of 3 fire elements and then cleanse and detox in your own private in-suite Infrared Sauna! Cook up a gourmet meal in our fully equipped chef's dream kitchen and year round Weber BBQ for grilling!

Location · Cleanliness · Amenities

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

Value · Location · Hot tub

Cozy Lakeside Cottage Getaway, W/ Private Hot Tub

Experience the best that Lake Simcoe has to offer in this stylish and comfortable retreat. You can enjoy swimming, boating, and fishing to your heart's content. Inside, you'll find a tastefully decorated living space, comfortable bedrooms, and a fully equipped kitchen. With so much to do in the area, including golfing and skiing, you'll never run out of things to do. After a fun-filled day, relax in the hot tub and watch the sunset over the lake.

Family · Location · Comfort

Luxury Waterfront French Chateau for Large Groups!

Welcome to the French Chateau! Escape to this stunning four-season lakeside retreat on the shores of Lake Simcoe. With sweeping water views, vaulted high ceilings and a timber-hybrid design, the home feels warm and elevated. Spend slow mornings on the dock, gather for long dinners with lake views, then unwind by the fire as the sun drops behind the water. A place made for connection, comfort, fun and unforgettable moments with your loved ones.

Family · Value · Layout