Vacation rentals in Keswick

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

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.

Luxury Waterfront Cottage Hot Tub & Amazing Sunset

Private lakefront cottage on Lake Simcoe with hot tub, stunning sunset views, and a rare shallow sandy-bottom waterfront — a unique feature rarely found on the lake. Perfect for large families and group getaways near Toronto, just minutes from Hwy 404. Enjoy swimming, kayaking, paddleboarding, fishing, BBQ, fire pit, and a private dock. Features 6 bedrooms, 4 bathrooms, a chef’s kitchen, and spacious open-concept living. Close to town, yet private, peaceful, and perfect for waterfront getaways.

Stylish, Modern 2nd Floor Private Apt. Quiet Area

Located in a beautiful and quiet neighborhood, this modern apartment can make for a perfect peaceful getaway no matter the occasion. Close to Lake Simcoe, beautiful beaches for swimming & fishing, and plenty of nature trails. Highlights: Large and cozy bedroom with ample storage and work space. Beautiful open concept dining area and kitchen with everything you need. Keurig coffee, tea and some snacks provided. Comfy sofa in front of a large screen TV with Netflix. High speed internet provided.

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.

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! 🌞🌲

Luxury 4BR Retreat ~ By Lake Simcoe ~ Full Privacy

Welcome to our Newly Furnished and Professionally Cleaned home in Georgina - minutes drive to Lake Simcoe! ✓ 4 BR, 3.5 WR - 100% Private & Spotless ✓ Just 5 Minutes to Keswick Beach ✓ Fully equipped kitchen for preparing meals ✓ Cozy Family & Living Rooms ✓ High-quality Linens. Comfy Beds ✓ 70" Smart TV, High-speed WiFi ✓ Laundry washer & dryer ✓ Private Backyard ✓ Free parking! ✓ Safe neighbourhood Book your stay with confidence and make unforgettable memories!

Quiet Country Escape Close To Beach Parks And Golf

Welcome to your country retreat! Kick back and relax in this quiet very comfortable, secluded guest suite with its own private entrance and is not shared making it 100% yours to enjoy. Perfect for beach and water enthusiasts, cyclists, golfers, fishing & boating. Located 4.4 kms from beaches to beautiful Sibbald Park & 6 km from shopping in both Keswick or Sutton. The ROC and many beaches and golf courses are a short bike ride or drive away!

Quiet Private Retreat - Entire Space & Cozy

Welcome to our cozy suite, your perfect private retreat. Soft beige walls and warm lighting create a comforting atmosphere in our open-concept space. Unwind in the sleeping area or kick back in the living and dining areas with a good book or work. Our separate entrance ensures complete privacy, allowing you to come and go as you please. Make yourself at home in our warm and inviting place, your home away from home. License #BL2023-00257

Lake Days & Cozy Nights – Your Year-Round Retreat

Cozy, family-friendly cottage just a short walk from the lake! Enjoy peaceful mornings on the porch, fun afternoons exploring nearby trails or public lake access, and evenings by the firepit. Perfect for families or friends, with a fully equipped kitchen, comfy spaces, and games for all ages. Relax, reconnect, and enjoy a quiet getaway surrounded by nature—where making memories is easy and the pace is slow.

5 bdrm home with pool and private lakefront

Relax with the whole family at this peaceful retreat with a pool and private lake access just 7 minutes from the 404 and 45 minutes from Toronto. Enjoy breathtaking sunsets and swim safely in the sandy-bottomed lake, 3-6 feet deep within 150 meters of shore. Nestled in a quiet neighborhood yet close to supermarkets, restaurants, and LCBO, this retreat has everything for an unforgettable stay.

Cheerful 2-bdrm cottage 2 minute walk to the lake

Relax with the whole family at this peaceful place to stay. The house features a full kitchen and beautiful large deck and backyard with BBQ grill. This freshly renovated cottage is 2 minutes walking distance to the lake, 1 km to Sibald Point park, and close to various other beaches. Many stores such as Sobeys, LCBO, GIant Tiger, etc are 5 minutes away.