Vacation rentals in Orr Lake

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Top-rated vacation rentals in Orr Lake

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite

A quaint blue cottage features a welcoming front deck with two yellow chairs facing the lush green lawn. The cottage is surrounded by trees and showcases large windows that bring natural light into the interior.

Tiny home in Waubaushene

Saltbox by the Bay +Views, Bikes, Vetta | 4-Season

*SEPTEMBER AVAILS* *GUEST BIKES* Welcome to Saltbox by the Bay, a cozy vintage cottage with beautiful views & luxe amenities. Perfect as a couple's getaway, small family/friends vacation or solo retreat. Ease into slow living, cook your favourite meals, play boardgames & albums, as you watch birds & sunsets over the lake. Stroll or ride guest bikes on the Tay Shore Trail. Visit Quayle's Brewery, glow-in-the dark bowl, pamper yourself at Vetta Spa & explore charming towns around Georgian Bay.

LocationValueDecor

5.0 out of 5 average rating, 277 reviews

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.

LocationFamilyHiking

4.98 out of 5 average rating, 57 reviews

Top guest favorite

The exterior of a modern cottage is framed by tall trees and colorful foliage. A spacious deck wraps around the cottage, providing outdoor seating options. The gravel pathway leads to the entrance, surrounded by natural landscaping and decorative stones.

Cottage in Tiny

Fall Escape - dazzling colours & stunning beach

Insta: @woodwardbythebeach 3min walk to the area’s most beautiful beach, sunsets & trails, you'll be sure to get lost in the serenity of the sand dunes year round Outdoor fire pit- s'mores included! Enjoy the BBQ, deck, & patio; the wine is on us! Fast WIFI for streaming movies or work from cottage Area is secluded yet central. 10min to Midland, close to Balm Beach - arcade, gokart, restaurant, & bar Ski/Hike/Snowmobile then unwind in a peaceful winterized home getaway with indoor fireplace

ValueFamilyWifi

4.97 out of 5 average rating, 133 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.

FamilyAccessWalkability

5.0 out of 5 average rating, 19 reviews

Top guest favorite

Guesthouse in Midland

Hillside Studio • Midland • Cozy Fall Escape

Welcome to the Hillside Studio — a bright, spacious 900 sq. ft. private guesthouse in the heart of Midland. Perched on a hillside, this modern one-bedroom retreat is designed for comfort and relaxation for 1–2 guests. Perfectly located to explore Georgian Bay: • 10-min. walk to stroll & shop Midland's charming downtown • 10-min. drive to Midland Golf & Country Club/Brooklea • 20-min. drive to hike Awenda Provincial Park trails • 30-min. drive to relax at Vettä Nordic Spa/Quayle’s Brewery

LocationNearbyAccuracy

5.0 out of 5 average rating, 42 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.

LocationValueSleep quality

4.96 out of 5 average rating, 183 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.

ValueFamilyAmenities

4.98 out of 5 average rating, 156 reviews

Superhost

Home in Hillsdale

Lost in Hillsdale | Heated POOL | Near Horseshoe

🏡🌲 Lost in Hillsdale | Spacious Getaway Near Horseshoe Valley Welcome to Lost in Hillsdale — a bright and spacious 4-bedroom retreat perfect for families and groups. Enjoy separate living and family rooms, a fully equipped kitchen, and plenty of space to relax and gather. Just 10 minutes from Horseshoe Valley and 20 minutes from downtown Barrie, with a summer pool and parking for 6–7 cars, this home is ideal for both adventure and relaxation. Unwind, explore, and feel right at home.

ValueFamilySleep quality

4.78 out of 5 average rating, 36 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.

FamilyValueSkiing

4.85 out of 5 average rating, 113 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.

FamilyValueAccess

4.95 out of 5 average rating, 126 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.

LocationValueSkiing

4.9 out of 5 average rating, 21 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!

FamilyValueSkiing

4.95 out of 5 average rating, 39 reviews