Waterfront vacation rentals in Midland

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Top-rated waterfront rentals in Midland

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

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Top guest favorite
A glass table is set on a balcony, featuring an ice bucket holding a bottle of sparkling wine, accompanied by two elegant glasses. Soft string lights provide gentle illumination, enhancing the cozy atmosphere. A potted plant adds a touch of greenery.
Condo in Innisfil
4.99 out of 5 average rating, 183 reviews

Fire & Ice Spa w/ Private Sauna!

Welcome to the most unique suite at Friday Harbour Resort! Relax, refresh and unwind in your very own private spa experience which includes large infrared sauna, 3 indoor fireplaces and outdoor fire table. Kiss those winter blues away while you warm up in the most cozy suite, perfect for a romantic getaway. Every stay includes a bottle of bubbly to toast with the one who is most important to you! Make Fire & Ice your next vacation destination and reconnect in a most romantic, relaxing suite!

Top guest favorite
A winterized cottage is surrounded by snow-covered terrain and tall trees. The exterior features large windows and a wraparound deck, offering views of the natural landscape. A black railing lines the deck, and a snow-dusted pathway leads to the entrance.
Cottage in Tiny
4.97 out of 5 average rating, 127 reviews

Cozy Winter Escape - Ski, Hike & Chill by the fire

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

Guest favorite
A serene lakeside scene is captured at sunset, with vibrant hues of pink and purple reflecting on calm waters. Silhouetted trees line the shore, and subtle rock formations add depth to the landscape.
Cottage in Waubaushene
4.81 out of 5 average rating, 177 reviews

The Cottage on Coldwater; where bay & trail meet.

Georgian Bay on one side and the Tay Trail on the other, this lakeside cottage offers gifts for all seasons. With spectacular views of the bay ready 4 ice fishing, sledding, skiing and snow shoeing over winter; hiking, biking, boating and swimming over summer with infinite possibilities in between, we're sure Waubaushene will suit your needs. Close to quaint Coldwater stores, kilometers of Parks, a short drive to 2 ski hills and just off Hwy 400, this hidden gem can accommodate adventure.

Guest favorite
Cottage in Tiny
4.96 out of 5 average rating, 141 reviews

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.

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
4.98 out of 5 average rating, 127 reviews

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.

Guest favorite
The cabin features a cozy exterior with a textured roof and large windows, surrounded by colorful fall leaves. Outdoor furniture is positioned on the deck, and a hot tub is visible. The setting is enhanced by the backdrop of vibrant autumn foliage.
Cabin in Innisfil
4.94 out of 5 average rating, 156 reviews

Lakefront Cozy Cottage w Hot Tub!

On Lake Simcoe this cozy retreat is just an hour north of Toronto Enjoy the stunning sunrises / views and access to a variety of water activities, while the surrounding area provides ample opportunities for hiking, skiing, other outdoor pursuits with many amenities closely. Down the street from Friday Harbour, LCBO, Starbucks 5 star rating a must & ALL guests to be added to booking. Honey, our golden doodle will greet and visit with you. The cabin is to be left SAME as you found it.

Top guest favorite
The exterior of a custom-built log cabin is framed by trees under a clear blue sky. A spacious porch features two Adirondack chairs and a fire pit, providing a welcoming outdoor space. Natural stone accents enhance the cabin's rustic charm.
Chalet in Gravenhurst
4.94 out of 5 average rating, 264 reviews

Log Cabin on the Lake Bed and Breakfast

Log Cabin on the Lake Bed and Breakfast We provide a 1st morning continental breakfast A Lakefront getaway for couples with an amazing view. Experience tiny home living in a custom built Log Cabin. Landscaping provides privacy for all parties (owner next door) we have parking for a boat , with 2 launches within 5 min. One into Morrison Lake the other into the Trent Severn . cross country skiing, ice fishing, water skiing swimming boating. Ready to escape, our Log Cabin could be it.

Top guest favorite
A serene sunset is captured over Georgian Bay, with warm orange and gold hues reflecting on the water. Silhouetted figures are seated on a dock, gazing out towards the horizon, creating a sense of tranquil evening ambiance.
Home in Victoria Harbour
4.84 out of 5 average rating, 149 reviews

Georgian Bay Paradise

Enjoy a relaxing vacation away from the hustle & bustle in this delightful 3 bedroom waterfront cottage. Just 90 minutes north of Toronto, this newly-renovated, gorgeous retreat is right on Georgian Bay, one of the world's most sought after destinations. Revel in breathtaking views, amazing sunsets and the privacy of numerous cedars. You will love the sun, sand, rock and waves which will captivate you. Access your own deck, lawn, and beach as well as many fun winter activities.

Top guest favorite
Cottage in Gravenhurst
4.98 out of 5 average rating, 101 reviews

Muskoka Cottage Getaway with Sauna

Welcome to your Lakefront Muskoka oasis, where epic sunrises greet you each morning and a private sauna awaits your return after a day on the lake. Surrounded by nature, this cozy retreat offers the perfect blend of relaxation and adventure, making it an ideal getaway for couples and families. Enjoy our fully updated outdoor space with a brand new deck, fire pit space and cedar barrel sauna that offers views of the lake. Located only a short 1.5 hour drive from Toronto.

Top guest favorite
Two wooden Adirondack chairs are positioned on a lush green lawn facing the water, framed by overhanging tree branches. The sunset creates a colorful display on the horizon, reflecting on the calm surface of the lake, while a small table holds a wine bottle and glasses.
Guesthouse in Victoria Harbour
4.96 out of 5 average rating, 279 reviews

Sunset Beach Cottage

Part log treehouse, part beach house and 100% of what you need to enjoy a peaceful getaway only 1.5 hours from Toronto! Walk up the private staircase and pause to enjoy the spectacular treetop and waterfront views from your own wraparound deck before entering your 900 sq. ft. oasis. Enjoy access to your own lawn, picnic table and beach* area and all that Georgian Bay and the area has to offer. *water levels fluctuate Insta: sunset_beach_cottage_canada

Superhost
An aerial view captures a waterfront community at sunset, featuring modern buildings along the marina. Boats are docked at the waterfront, and a serene lake reflects the warm colors of the sky. Lush greenery lines the horizon, adding a sense of tranquility.
Cottage in Innisfil
4.88 out of 5 average rating, 338 reviews

Boardwalk Bliss For Two *1 hr From TO!*

Waterfront Escape – 1 Hour from Toronto! Enjoy a private, street-level retreat steps from the marina boardwalk! Perfect for a relaxing getaway or remote work, with fast WiFi and in-room entertainment. 🌊 Activities Nearby: Waterside Dining & Boardwalk Music Nature Trails, Golf & Spa 🚤 Optional Add-Ons: ✔ Boating Excursions (Pre-Book) ✔ Dining & Activity Combos 📆 Book Now – Dates Fill Fast!

Top guest favorite
A colorful seating area features a bright, multi-colored sofa alongside a contemporary black shelf. A mirror is positioned above the shelf, which holds decorative items and books. Natural light enters through large windows, illuminating the warm wood flooring.
Condo in Innisfil
4.99 out of 5 average rating, 265 reviews

Boho by the Bay

BlogTO writes: " Friday Harbour Resort is a vibrant, upscale destination...That's perfect for a quick getaway..., with plenty of cool restaurants and shops, a waterfront pedestrian village, and year-round recreational activities." I encourage you to search eventsatfridayharbour to see what is seasonally available. if after searching, you still have questions or need clarification, please ask!

Popular amenities for Midland waterfront rentals

When is the best time to visit Midland?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ555ﺩ.ﺇ510ﺩ.ﺇ580ﺩ.ﺇ569ﺩ.ﺇ731ﺩ.ﺇ1,091ﺩ.ﺇ1,131ﺩ.ﺇ1,256ﺩ.ﺇ962ﺩ.ﺇ801ﺩ.ﺇ698ﺩ.ﺇ771
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Quick stats about waterfront rentals in Midland

  • Total vacation rentals

    Explore 40 vacation rentals in Midland

  • Nightly prices starting at

    Midland vacation rentals start at ﺩ.ﺇ220 per night before taxes and fees

  • Verified guest reviews

    Over 2,130 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Midland vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Midland rentals

  • 4.8 Average rating

    Midland stays are highly rated by guests—averaging 4.8 out of 5!

Destinations to explore

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