Holiday rentals in Keswick

4.93 out of 5 average rating, 271 reviews

A cozy living area features a couch facing a 55" television, placed on a low white media console. A floor lamp provides additional lighting, while a small coffee table adds functionality. Doorways can be seen in the background, leading to other areas of the suite.

Guest suite in Newmarket

2 Bed-2Bath-Kitchen | Private | Family-Couple-Work

We have an ideal place for you regardless of work, pleasure, or family time. The recently renovated suite includes: - Separate keyless entry - 2 bedrooms with closets - Living room with 55" TV - Full kitchen with storage & dining - 2 full bathrooms (1 en suite) - 2 on-premises Parking - Laundry - WiFi & more FAST EV Charger-Check for availability ($15/charge) CENTRAL LOCATION! Steps to Upper Canada Mall, Groceries, Restaurants, Trails, Parks, Golf Course, Costco, Walmart, Highway, Go, & more

Dome in Bradford West Gwillimbury

Vibrant autumn foliage displays shades of yellow and orange surrounding a geodesic dome. A pathway of stone steps leads through a lawn covered in colorful leaves, creating a serene outdoor setting amidst lush greenery.

Four season glamping dome under the stars

Whether you are looking for a romantic getaway for two, a solo remote work week in solitude surrounded by nature, or a family adventure, this 4-season geodesic dome is just the right place. Explore picturesque trails of Scanlon Creek Conservation Area, enjoy inground pool in summer, experience breathtaking sunsets over the farm fields, the starry skies by the bonfire, mesmerizing dance of fireflies in June, and let the frogs and crickets lull you to sleep in the place where time stands still...

4.97 out of 5 average rating, 503 reviews

5.0 out of 5 average rating, 35 reviews

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

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.

4.96 out of 5 average rating, 106 reviews

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!

4.9 out of 5 average rating, 217 reviews

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.

4.89 out of 5 average rating, 54 reviews

Sunset Harmony on Cook’s Bay

🌅 SUNSET HARMONY | Cook's Bay Waterfront Retreat One of the last chances to enjoy summer on beautiful Cook's Bay! Escape to our 4.88★ waterfront retreat for families and groups. 🏡 Main House + Private Studio (exclusive use) ✔ 4 bedrooms • 3 bathrooms • 2 kitchens ✔ NEW private dock with lake access & swimming steps ✔ Year-round hot tub & wood-fired sauna ✔ Kayaks, paddle boards & paddle boat ✔ Spacious pergola deck with west-facing sunsets Relax, reconnect, and create unforgettable memories.

A cozy family room is accented with a large, grey sectional sofa and a decorative orange throw. A wooden coffee table sits at its center, while a Smart TV is mounted on the wall. Light streams in through the large windows, leading to a covered outdoor deck.

4.89 out of 5 average rating, 71 reviews

Tranquil Modern Cottage, Simcoe Lake

3 Bedrooms equipped with queen brand new mattress, sheets, pillows & blankets 2 full bathrooms Family room & Smart TV Washer& Dryer Full Kitchen including dish washer, stove/ oven, toaster, coffee maker and microwave covered deck with brand new outdoor patio furniture and gas fire place dining set inside & outside in gazebo 6 Free parking spaces 5 minute walk to Simcoe lake Entertainments: table tennis, Backgammon, Chess, Jenga Kayak, paddle board & Jet skies rental nearby Highspeed internet

4.96 out of 5 average rating, 144 reviews

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!

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.

4.81 out of 5 average rating, 128 reviews

Superhost

4.67 out of 5 average rating, 67 reviews

Beautiful Waterfront Cottage with Pool&HomeTheater

🌲Lake Simcoe Getaway Escape to our rustic-chic Lake Simcoe retreat—perfect for families and friends! Enjoy a private swimming pool, sunny backyard with BBQ, cozy pool table, and a premium home theater for unforgettable movie nights. Just minutes from the lake, this farmhouse-style cottage blends relaxation and fun. Whether you're exploring scenic trails or relaxing by the pool, it's the perfect spot to unwind and create lasting memories. Book your getaway today! 🌞🌲

An open-concept living area features a spacious sectional sofa and a wooden dining table surrounded by white chairs. Bright lighting illuminates the room, highlighting the modern kitchen with sleek cabinetry and stainless appliances. Large windows allow natural light to enhance the inviting atmosphere.

4.88 out of 5 average rating, 90 reviews

Cozy 4 Bdr Cottage Near Lake Simcoe & Beaches

The relaxing, quiet, and bright newly renovated cottage has stunning nature. Just within walking distance of Lake Simcoe and De La Salle's famous beach. The perfect getaway with all the comforts. Have fun with the whole family at this stylish place. Brand new orthopedic mattresses in every bedroom. Nearby restaurants, grocery stores, LCBO. Free fiber internet. Smart TV. Free, up to 7 vehicles on-premises parking. Excellent winter fishing.

An open-concept living room is highlighted by natural light pouring in through large arched windows. A comfortable white couch is paired with accents of black and brown. A decorative fireplace adds warmth, while modern furnishings create a welcoming atmosphere.