Vacation rentals in Port Bolster

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.

Off-grid Glamping Dome Nestled in the Woods

Welcome to our private campsite in Utopia, ON. Our family’s glamping dome is your chance to experience a unique getaway surrounded by the sights & sounds of nature. Amenities include camping essentials & some glamping perks: king size bed, bbq, fireplace, Indoor incineration toilet, soap & water, outdoor shower (summer only), kettle, cooking utensils. Nearby is Purple Hill Lavender Farms, Drysdale's Tree Farm, Tiffin Conservation Area, Nottawasaga & golf courses. Wasaga Beach is 30 min away.

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.

Luxury Beach Spa w/ Private Sauna & Oasis Patio!

Escape to the Beach at Friday Harbour Resort in our newest addition to our Spa Getaway Group of professionally designed suites that will take you to a luxury destination close to home! This stunning Miami Boho Beach Hotel type vibe suite is very spacious and boasts 3 fire elements (indoor & Out) and your own private in-suite Sauna! With 2 beds and 2 baths there is plenty of space for a couples, friends or family stay! Make memories that last a lifetime in our most unique experience suites!

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!

Bird Haven Log Cabin

Embrace the log cabin charm. Bright & cheery, historic & unique. Fully renovated with all the modern conveniences. Starlink internet and EV charger. Close to an extensive variety of activities, walking trails, Lake Simcoe, lake side parks, restaurants, golf courses, skydiving, antique markets, shopping, casino & racetrack. Living room features comfy sectional, cathedral ceilings, floor-ceiling stone fireplace & 50" TV. Well equipped brand new kitchen. Dine inside or al fresco on the patio.

Life is Better at the Cottage

4 Guests, 2 Bedrooms, 3 Beds . Open Concept High Ceiling 2 Bdrm Waterfront Cottage in the Beautiful Kawartha Lakes . Walkout to a Massive Covered Wrap Around Deck Overlooking Canal Lake for your enjoyment; Rain or Shine . Yoga on the Dock or on the Deck . Layback and read a book . Use of Kayaks and Adult Life Jackets are included . Great fishing (Bass, Pike, Walleye, Crappie and more) . Duck and Goose Hunting starting mid September. . 1.5 hours Away from GTA . 5 minutes away from Kirkfield

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.

Glass Dome - Sleep Under The Stars- Free Sundays

Discover this new, stunning 22ft Glass Geodesic Dome nestled in the heart of Uxbridge. Imagine waking up surrounded by 360-degree panoramic views of the natural landscape Please note... its FULL WEEKEND STAYS ONLY - BOOK FRIDAY AND SATURDAY-SUNDAY IS FREE. This allows guests to fully enjoy their Sunday without feeling rushed to check out at 11am. Enjoy all day Sunday with option of staying the evening. 8X12 BUNKIE NOW AVAIL. SLEEPS 4 ( 2 bunk beds) $100 flat fee

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.

Lake Simcoe 5BR 4BA Sleeps 12 | Beach Access

Your crew's summer escape on Lake Simcoe — beach, fire pit, and room for 12. Modern 5BR/4BA home built for groups. Spread out, stay up late, actually relax. • 5 bedrooms, 4 bathrooms • 2 living rooms + open kitchen/dining • Private beach access on Lake Simcoe • Fire pit + huge backyard • Parking for 12+ vehicles, boats & trailers welcome • AC throughout • Keypad self-check-in — no coordinating • 815 sq ft garage for gear & kayaks Close to Barrie and Orillia.

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.