Cottage holiday rentals in Penetanguishene

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

Family · Location · Decor

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.

Family · Value · Quiet

Charming riverside cottage, B&B license

Charming riverside cottage available on Wasaga Beach. Just a 4-minute stroll from a pristine sand beach. Immerse yourself in nature's beauty while enjoying modern amenities, including a private hot tub for relaxation. Unwind with a friendly round of mini-golf or gather around the fire pit for cozy evenings under the stars.Create lasting memories at this perfect oasis that combines riverside tranquility, mini-golf fun, hot tub relaxation, and the warmth of a fire pit. Your dream getaway awaits!

Value · Location · Decor

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.

Value · Family · Pool

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.

Family · Location · Decor

Lakefront | Hot Tub, Private Dock & Sandy Beach

Luxury lakefront cottage on Lake Simcoe with a rare shallow sandy-bottom shoreline, private dock, and hot tub—perfect for swimming and family fun. Enjoy breathtaking sunsets, kayaking, paddleboarding, fishing, BBQs, and a fire pit. Ideal for family vacations, holiday getaways, and group retreats near Toronto, minutes from Hwy 404. Features 6 bedrooms, 4 bathrooms, a fully equipped kitchen, and an open-concept living area. Private, peaceful, and perfect for unforgettable memories year-round.

Value · Family · Parking

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.

Value · Family · Check-in

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.

Value · Family · View

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

Value · Location · Sleep quality

Cider Haus | Lakefront Sauna & Fenced Yard

Welcome to Cider Haus, a quaint four-season Muskoka cottage on Brandy Lake, just five minutes from Port Carling. Spend summer days swimming and paddling, unwind in the lake-view sauna, and gather around the natural-stone fireplace when the weather turns cool. With a fully fenced yard, equipped kitchen, and thoughtful comforts throughout, it's a welcoming lakefront retreat for couples, friends, families and pets.

Family · Value · Barbecue

Foster's Landing - Log Cottage on Lake Muskoka

Relax, play, or work from "Home" at this new Log Cottage on Lake Muskoka. The property features 3 bedrooms, a fully-featured kitchen, bathroom with rain shower, Great Room with seating, dining space and cathedral ceilings, a large elevated deck with BBQ, an additional large portion of covered deck, a basement laundry room with washer and dryer, and ample open spaces at the front, side, and rear of the cottage.

Location · Value · Barbecue

Muskoka Luxury Cottage.Hot Tub/Outdoor Steam Sauna

Quaint, cozy, cottage on Mirror Lake in the heart of Port Carling. A family friendly getaway for all ages! This stunning waterfront property is in between Lake Muskoka and Lake Joseph. The perfect spot for family and friends to get together and make memories. Sauna, hot tub. Quiet and peaceful, yet so close to shopping, dining, LCBO, and golfing. Please note air hockey table is under repair.

Location · Family · Hospitality