Cottage holiday rentals in Midland

4.93 out of 5 average rating, 107 reviews

A modern lake house exterior features a spacious deck with four red chairs facing the water. Lush green grass and well-maintained flower beds surround the wooden deck. Large windows allow ample natural light into the interior, enhancing the connection with the outdoor environment.

Cottage in Port Mcnicoll

Georgian Bay Waterfront Cottage HotTub King Bed

Escape to this exceptional modern Lake house on Georgian Bay shores. Enjoy Incredible sunsets and views while you unwind in the hot tub or around the fire. Use the Kayaks to explore the Georgian Bay shores. This home can accommodate up to 4 adult guests (one additional child) Our quite property is best suited for 1 to 2 couples or a family of 5 or less and is fully equipped so you can relax on your next summer or winter getaway. Add the waterfront Bunkie to your summer stay (see additional fee)

A spacious living area is highlighted by a large white stone fireplace, surrounded by comfortable seating. Natural light filters through sheer curtains, enhancing the warm atmosphere. A flat-screen television is mounted above the fireplace, and a wooden dining table sits elegantly in the foreground.

4.97 out of 5 average rating, 132 reviews

Summer Getaway - 3 min walk to Beach, Clean & Cozy

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

The exterior of the cottage showcases a charming two-story structure with a covered porch. Warm lighting illuminates the entrance, while a wooden staircase leads to the front door. Lush greenery and a stack of logs add a natural touch to the inviting atmosphere.

4.88 out of 5 average rating, 107 reviews

Forest Oasis in Tay w/Large Jacuzzi Hottub

Beautiful cottage situated on the most southern point of Georgian Bay in Victoria Harbour. Less then 2 hours from the GTA with full amenities including an LCBO and Foodland 5 minutes away. Take advantage of plenty outdoor activities. Enjoy a bike ride on the stunning Tay Shore Trail, swimming in the lake on a hot summer day or hit the local slopes at Mt St Louie during the winter. Regardless of your choice in activities, end the evening with a soak in the hottub. Don't forget to look for stars!

The cottage is situated on a well-maintained lawn, framed by trees, with a spacious deck accessible via a stone pathway. Colorful kayaks and a paddle boat are visible by the water, and the sky displays a warm sunset with varying shades of orange and purple.

4.85 out of 5 average rating, 190 reviews

Waterfront Paradise on the Georgian Bay

This beautiful cottage of 2950sqft faces a breathtaking view of the Georgian Bay with over 105ft of lakefront. During the summer, this cottage is perfect for ATV and bike trails, wateractivities and fishing. The cottage includes kayaks and a paddle board for the guests to enjoy. During the winter, the cottage is ideal for ice fishing and is only a 13 minute drive to Mount St. Louis skiing. Under 10 minute driving distance to beaches, Tim Horton’s, LCBO, gas station, ice cream parlour and more.

A cozy corner features two checkered chairs positioned near a stone hearth. Natural light filters through a large window, highlighting the textured wall. A small table topped with a potted plant adds a touch of greenery, while the warm surroundings evoke a sense of comfort.

4.83 out of 5 average rating, 248 reviews

Serenity, Simplicity and Stone

This is a tiny cottage in a sleepy little hollow that opens onto the Georgian Bay. Inside, each stone was carefully chosen and the woodwork was built, piece by piece, by two craftsmen who are highly skilled and passionate about repurposing. It's an art that will leave you in awe; especially if you're worried about climate crisis. The coat hangers are upcycled 100-year-old railway spikes! If you're looking for luxury you will be disappointed but if you're a minimalist you're going to love it.

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.

4.96 out of 5 average rating, 177 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.

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.

4.82 out of 5 average rating, 198 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.

4.98 out of 5 average rating, 153 reviews

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.

The cottage is nestled among tall trees, surrounded by lush greenery and vibrant flowers. Soft lighting from the windows casts a warm glow, emphasizing the inviting atmosphere. Stone pathways and landscaping create a harmonious blend with the natural setting.

4.84 out of 5 average rating, 163 reviews

The Bay View Cottage w/hot tub

Welcome to our 4 season, 2 family cottage with Georgian Bay views and a hot tub. 3 min walk to the cutest small beach that has stunning sunsets, 12 min to Awenda Provincial Park which has great hiking, beaches, biking and winter activities. Short drive to Balm Beach. Downtown Midland has great restaurants and everything a quaint downtown has to offer. Winter has so much to offer including ice fishing, OFSC snowmobile trails, cross country skiing and much more. Max occupancy is 8 adult.

4.97 out of 5 average rating, 118 reviews

A charming cottage sits nestled amongst trees, featuring a spacious wooden deck with several white lounge chairs positioned for outdoor relaxation. A gradual sandy beach area with rounded rocks is visible, leading to calm waters of Georgian Bay.

Cottage in Port Mcnicoll

Stunning Waterfront Cottage & Bunkie!

Beautiful 2-bedroom Cottage plus 1-bedroom Bunkie on Georgian Bay! Located in a quiet area with a private beach! In the summer the lake is perfect for swimming! Just bring water shoes as there can be rocks and zebra muscles. We have a two-person kayak, perfect for a day out on the water. In the evening, curl up by the outdoor fire pit, roast marshmallows and enjoy the amazing sunsets! It is the perfect place for a summer getaway! Please note this cottage is Pet Free.

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.

4.96 out of 5 average rating, 112 reviews

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.

A warm living area features a stone fireplace as the focal point, with a cozy fire burning inside. Comfortable leather seating is arranged around a rustic wooden coffee table, complemented by small decorative items and soft textiles, while glass doors lead to another space.

4.93 out of 5 average rating, 362 reviews

Bluestone

Bluestone is located less than 10 minutes' drive from beautiful Awenda Provincial Park in Tiny, Ontario. Every choice was made with guest comfort in mind. In the Summertime, take a short walk down a wooded path to Georgian Bay and perfect swimming, or explore a hiking trail and take in the natural beauty of the area. In Winter, enjoy skiing and snowshoeing locally, or stay in, put a record on, and cozy up by the fire. Licence STRTT-2026-057

Popular amenities for Midland cottage rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

A charming cottage is seen surrounded by trees, with a large deck above. A fire pit is centrally located in the grassy yard, circled by several wooden chairs. A kayak rests nearby, hinting at outdoor activities, while the serene natural setting offers a peaceful retreat.

4.86 out of 5 average rating, 555 reviews

Charlie the Cottage | Hot Tub | Trail | Hike/Run

4.95 out of 5 average rating, 133 reviews

A unique wooden sauna, shaped like a barrel, is placed on a grassy area by the lake. Above, a clear night sky is filled with bright stars, providing a serene backdrop. Nearby, lounge chairs are arranged on the lawn, with trees lining the water’s edge.

Cottage in Coldwater

Cottage on the Rocks - with Hot Tub and Sauna!

4.8 out of 5 average rating, 127 reviews

Georgian Bay Cottage-HotTub/Sauna/Swim/Hike/Marina

4.94 out of 5 average rating, 298 reviews

A circular stone fire pit is surrounded by wooden Adirondack chairs, offering a cozy gathering space. A vibrant fire burns in the center, with lush greenery and a serene riverside view in the background under a colorful sky.

Cottage in Wasaga Beach

Charming riverside cottage, B&B license

A furnished outdoor deck is surrounded by trees, featuring a cozy seating arrangement with grey cushions. A gas fire pit sits in the center, accompanied by a wine bottle and glasses. An umbrella provides shade, and a TV is mounted on the wall.

4.97 out of 5 average rating, 104 reviews

Tiny Oasis: Family Beach Cottage *HOT TUB & SAUNA*

4.91 out of 5 average rating, 301 reviews

Cottage in Georgina

Lakefront | Hot Tub, Private Dock & Sandy Beach

4.95 out of 5 average rating, 179 reviews

A spacious hot tub overlooks the Severn River, surrounded by greenery. Chairs are positioned nearby on the grassy lawn, providing a relaxing space to enjoy the water views and sunshine. The calming river scene features boats gently cruising by, enhancing the outdoor experience.

Cottage in Severn Bridge

CARL in Muskoka: Waterfront Cottage with Hot Tub

A welcoming entrance features a wooden gate with the name 'Eagle Point' prominently displayed. A tree-lined gravel driveway leads to a charming cottage with wood siding and a green roof nestled among the trees.

4.82 out of 5 average rating, 193 reviews

Hot Tub & Sauna Retreat by Georgian Bay Trails

Pet-friendly cottage rentals

4.84 out of 5 average rating, 296 reviews

Cottage in Lafontaine

Cozy Beach Cottage with Pool | Georgian Bay

Cottage in Penetanguishene

A welcoming outdoor deck features wooden railing and a shaded seating area with a patio umbrella. The deck is surrounded by lush greenery, providing a serene setting. The home’s exterior showcases a blue facade with large windows allowing natural light to enter.

Tiny House in Penetanguishene

4.96 out of 5 average rating, 249 reviews

4.95 out of 5 average rating, 187 reviews

A calm lake setting is depicted, featuring a wooden dock extending into the water. Several ducks swim leisurely near the dock, with lush greenery lining the opposite shore. Fluffy clouds drift across a blue sky, reflecting on the tranquil surface of the water.

Cottage in Gravenhurst

Relaxing lakehouse + pool table & private docks

4.96 out of 5 average rating, 138 reviews

Cottage in Georgina

Resort-Style Luxury Waterfront Cottage

4.93 out of 5 average rating, 243 reviews

A serene lake view is presented from the shore, featuring a wooden dock extending over calm waters. Two boats are anchored nearby, while the surrounding trees offer shade. Sunlight reflects on the water's surface, creating a shimmering effect across the lake.

Cottage in Bracebridge

Charming cottage on Lake Muskoka

4.88 out of 5 average rating, 323 reviews

An inviting exterior of a single-story cottage is depicted, featuring a patio area with a table and chairs. A green umbrella provides shade, while landscaped garden beds and a pathway enhance the setting amidst lush greenery and a clear sky.

Cottage in Wasaga Beach

Cozy Riverfront Cottage with Dock

4.96 out of 5 average rating, 248 reviews

A serene lakeside scene is captured, featuring three red Adirondack chairs positioned near a fire pit. The calm water reflects the surrounding trees and sky, while logs are stacked nearby, suggesting a cozy gathering spot for evening fires.

Cottage in Bala

Lakefront Cottage with Sauna and Steam Room

4.98 out of 5 average rating, 126 reviews

Cottage in Gravenhurst

Where Lake Days Last Longer | Sauna + Beach

Private cottage rentals

4.94 out of 5 average rating, 82 reviews

An inviting living space features a wooden dining table surrounded by diverse seating options, including woven chairs. Natural light enters through multiple windows, illuminating the room's simple decor, including a comfortable sofa and a small accent table, with visible wooden beams overhead.

Cottage in Port Mcnicoll

Steps to Beach & Scenic Nature Trails -1.5h fromTO

Cottage in Penetanguishene

A wooden staircase leads up from the sandy beach to the charming cottage nestled among lush greenery. The cottage features a distinctive gray exterior, large windows, and a spacious deck that overlooks the surrounding nature.

Georgian Bay Waterfront Cottage with Sandy Beach

4.8 out of 5 average rating, 81 reviews

A spacious living area features a comfortable gray couch positioned across from a modern coffee table. Light wood paneling adorns the ceiling, while large windows brighten the room. A dining table is visible in the background, complemented by light-colored chairs.

4.87 out of 5 average rating, 47 reviews

Lake House on Sturgeon Bay

4.89 out of 5 average rating, 57 reviews

Cozy Cottage w/ Hot Tub/GameRoom near Beach/Skiing

A spacious two-story brick house is seen, featuring large windows and a welcoming front porch. The well-lit exterior is complemented by surrounding greenery and an expansive driveway. A garage can be observed to the left, suggesting ample parking and accessibility.

4.91 out of 5 average rating, 57 reviews

Grandview Family Beach House - Hot Tub & Sauna

Cottage in Penetanguishene

A serene outdoor seating area features two cushioned chairs and a small table, set on a wooden deck overlooking tranquil waters. Lush greenery and a clear blue sky create a peaceful backdrop, while glass panels ensure unobstructed views of the shoreline.

Beautiful & spacious all-season waterfront cottage

4.97 out of 5 average rating, 33 reviews

The front of the cottage features a wooden deck adorned with a trellis and warm string lights. A welcoming entrance is framed by two steps leading up to the porch, which has a seating area visible through the glass door.

4.94 out of 5 average rating, 36 reviews

Cozy All-Season Family Cottage

A year-round Jacuzzi hot tub is situated on a stone patio, surrounded by lush green grass and tall trees. A planter with vibrant flowers adds a touch of color nearby, creating a serene outdoor relaxation space.