Vacation rentals in Orr Lake

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Top-rated vacation rentals in Orr Lake

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Top guest favorite

A charming cottage is showcased with a stone facade, set against a backdrop of lush trees. A welcoming front entrance is framed by steps leading up to a porch, while a well-maintained lawn and walking paths enhance the inviting outdoor space.

Cottage in Elmvale

Lakefront Family-Friendly Cottage on Trails

Four-season family-friendly cottage on 2.5 acres of natures best including wooded trails and a private lakefront and Hottub. Summer: Situated on 156-feet of lakefront. The lake is shallow and warm, perfect for families to enjoy. Equipped with a BBQ, Two fire pits and a lakeside beach shack for guests enjoyment. 30 Minutes from Barrie, Midland, and Orillia. ~ 75-minutes north of the GTA. Winter: Bonfires, frozen lake, direct access to OFSC Trails. Short drive to four well known ski resorts.

4.98 out of 5 average rating, 54 reviews

Guest favorite

A spacious common area features a large, light-colored sectional sofa arranged around a warm fireplace built into a stone wall. Large glass doors provide access to a serene outdoor space, while natural light enhances the wood-beamed ceiling. Decorative elements include woven wall art and a wooden side table.

Cottage in Tiny

The Beach House, Georgian Bay, Beach View w/ Sauna

New!! A rare and stunningly designed cabin overlooking a semi-private beach on Georgian Bay. This tranquil 4-bedroom, 2-bathroom retreat is surrounded by trees with breathtaking views of the pristine bay. Every detail has been thoughtfully curated for your ultimate enjoyment. We include all linens, towels, sheets, firewood for in/outdoor fires, olive oil, salt, pepper, a fully equipped kitchen with utensils, PrimeTV, Netflix, Sonos, and more. Additionally, we are taking bookings for 28+ nights.

5.0 out of 5 average rating, 16 reviews

Guest favorite

A peaceful beach scene captures the soft sand shoreline leading to the water's edge. Gentle waves lap at the shore, and the sky is filled with warm sunset hues. A cottage is visible in the background, nestled among trees, enhancing the serene atmosphere.

Cottage in Tiny

Ultimate Georgian Bay Vacation Getaway

Come and stay at our beautifully renovated *all-season* beachfront cottage and enjoy a breathtaking panoramic view of Georgian Bay! You'll discover the cottage sitting atop a sand dune, right on one of the most stunning freshwater beaches in the world. This rare location hosts a private covered deck hovering over the white sand, in a beach house closer to the bay than anywhere else around! Summer guests also enjoy use of a heated salt water pool and large resort deck created by Paul Lafrance.

4.96 out of 5 average rating, 177 reviews

Top guest favorite

A tranquil lakeside view displays a spacious cottage with large windows, reflecting on the calm water. Surrounding trees and a clear blue sky add to the serene atmosphere, inviting relaxation and enjoyment of the natural beauty.

Cottage in Georgian Bay

Muskoka Stunning Cottage On Little Lake

Surrounded by Little Lake, this gem provides a relaxing getaway with amazing water views. Spend your days peacefully rowing on the lake or having a picnic on the private beach, and your nights settling by a crackling fire. The home itself is plenty spacious for unwinding and getting a good night's sleep, views all-inclusive. Explore Port Severn Park right next door and play around in the public beach and splash pad. For more adventure, hike the beautiful Georgian Bay Islands National Park.

4.98 out of 5 average rating, 153 reviews

Top guest favorite

A spacious living area features a modern stone fireplace with wood accents. High wooden beams accent the ceiling, illuminated by soft lighting. A cozy sofa is positioned in front, layered with a warm throw. An open staircase leads to a loft area, enhancing the room's airy feel.

Home in Coldwater

Moonstone chalet

Once a Presbyterian Church built in 1889 is now converted into modern chalet with entertaining family and comfort in mind. With 3 bedrooms and 2-1/2 bath you will be sure to be comfortable any time of the year. Around the corner from Simcoe walking/bike trails , Mount St-Louis ski hills, golfing Vetta Nordic Spa and Quales brewery. The nights beside the outside fire pit or the inside wood burning fireplace will keep you cozy and warm. You will be sure to create many family memories here.

5.0 out of 5 average rating, 24 reviews

Superhost

A hot tub is situated under a wooden gazebo, featuring railings and a ceiling adorned with decorative elements. Sunlight illuminates the scene, highlighting the inviting water surface. A view of the snowy landscape and frozen lake extends in the background, enhancing the serene atmosphere.

Home in Elmvale

Ski, Swim, Soak, Boat & Golf

Renovated 2 storey cottage overlooking beautiful Orr Lake. Ski at Mt. St. Louis Moonstone or Horseshoe Valley. Both 13 minutes away. A heated swimming pool in the summer and a hot tub all year. Canoeing, kayaking, paddle boarding or golfing across the street. Fully equipped kitchen. Livingroom includes an overhead projector, plus as a second floor Family room with a Wet Bar. 5 bedrooms, 7 beds, & 3 Baths. Max occupancy: 10 adults or 12 including children under 13. Parking for 5 cars.

4.85 out of 5 average rating, 110 reviews

Guest favorite

Villa in Tiny

In Pines •Family-Friendly • Screened Porch • Beach

Escape to In Pines — a bright and spacious retreat nestled in Tiny, LaFontaine, just a 3–4 minute walk to the beautiful sandy beaches of Georgian Bay. Wake up to sunlight streaming through large windows, enjoy peaceful mornings surrounded by nature, and unwind by the fire pit or on the cozy screened porch after a day at the beach. Designed for comfort and connection, this home is perfect for families and groups looking to relax, recharge, and create lasting memories in every season.

4.98 out of 5 average rating, 122 reviews

Guest favorite

Home in Hillsdale

The four season Mount St. Louis hideaway

Escape to this Mount St. Louis hideaway, a private two-acre country retreat tucked among mature trees just minutes from Mount St. Louis Moonstone. This four-season getaway blends rustic charm with elevated comfort, Perfect for ski weekends, family escapes, or relaxed group retreats. Wake up surrounded by nature, spend the day on the slopes or trails, and end your evenings soaking under the stars in the private swim spa! Make Endless memories at this unique and family-friendly home.

4.9 out of 5 average rating, 20 reviews

Guest favorite

A charming cottage features a bright yellow exterior surrounded by lush greenery. A wooden deck is furnished with red chairs and a gas barbecue. A path leads to the entrance, with a firepit nearby. Large windows provide ample natural light.

Home in Elmvale

The Yellow Cottage

Escape to our mini resort on Orr Lake! Just 15 mins from Midland & Barrie, our 5 fully updated cottages offer A/C, Heating, Wi-Fi, private deck and balcony, personal BBQ, and your own firepit. Enjoy our private beach, on-site specialty coffee shop, and weekend yoga/Pilates (during the summer) classes. Steps from trails and Orr Lake Golf, and close to shopping, dining, Horseshoe & Mt St Louis, and Vetta Spa. 4-season comfort with nature at your doorstep—your perfect getaway awaits!

4.95 out of 5 average rating, 39 reviews

Guest favorite

A sandy beach stretches out towards calm waters, complemented by a small dock and an island visible in the distance. Red and gray Adirondack chairs are setup in a semicircle on the beach, inviting relaxation under a clear blue sky dotted with clouds.

Home in Victoria Harbour

Welcoming Waterfront Cottage

Cozy yet stylish waterfront gem hidden in friendly Victoria Harbour minutes of driving from Midland, featuring spacious comfortable rooms, sandy beach with a dock for fun in the water, enclosed backyard great for the families with small children, an open concept main floor transitioning to the deck with stunning water views, and plenty of parking space - all in a peaceful neighborhood with a boat launching spot nearby, marina & local shops within walking distance.

4.95 out of 5 average rating, 37 reviews

Top guest favorite

A stone patio leads to a sandy beach, featuring a seating area with red chairs overlooking Georgian Bay. The calm water is visible in the background, framed by trees and large rocks, with yellow kayaks positioned along the shore.

Cottage in Tiny

Beautiful Beachfront Cottage.

Township of Tiny License Number: STRTT-2026-110 Enjoy our all-season paradise only 1.5 hours north of Toronto! In summer, enjoy the sandy beach waterfront with incredible views of Georgian Bay with the Town of Penetanguishene, and all its historic charm, only 20 minutes away! In winter, enjoy all the area has to offer with incredible OFSC groomed snowmobile trails and amazing ski resorts less than an hour away! *Contract to be sent and signed prior to stay.

4.96 out of 5 average rating, 112 reviews

Top guest favorite

Home in Victoria Harbour

Sunrise

This beautiful four bedroom lakefront cottage features huge windows that offer breathtaking views of the water and surrounding nature. Natural light floods every room, creating a warm and inviting space to relax in. The open-concept design connect the living, dining, and kitchen areas, making it perfect for entertaining or family gathering Step outside to enjoy the fresh air and peaceful sounds of the lake.

5.0 out of 5 average rating, 26 reviews