Waterfront vacation rentals in Orillia

A cozy living area features two armchairs and a comfortable sofa, arranged around a central coffee table. Large windows allow natural light to illuminate the space, showcasing views of the surrounding woods. A television and a stylish lamp enhance the room's functionality.

5 out of 5 average rating, 138 reviews

Relax at The Rock: Muskoka Waterfront Cottage

Enjoy fishing, swimming and paddling 22km of the green and black rivers. Paddleboat, canoe, 2 kayaks, and a SUP provided. Take the short 5 minute stroll into town for ice cream or fresh baked treats. Lay out on the elevated deck or in the screened in porch with a good book. End your evening at the riverfront firepit. Nearby day adventures include hiking, golfing, parks, beaches, breweries, casino rama, and downhill skiing at Mount St Louis Moonstone and Horseshoe Valley (30 minute drive).

5 out of 5 average rating, 164 reviews

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

Fire & Ice Spa w/ Private Sauna!

Welcome to the most unique suite at Friday Harbour Resort! Relax, refresh, unwind and rejuvenate in your very own 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! We know you will enjoy your stay and love the outdoor elements AND the indoor ones too!

Home in Nestleton Station

A calm lake scene is visible, featuring a wooden dock extending into the water. Two chairs are positioned on the dock, inviting relaxation. Lush greenery surrounds the area, with trees framing the view, and gentle ripples on the lake reflect the clear sky.

4.99 out of 5 average rating, 133 reviews

Retreat 82

Located just a little over an hour from Toronto, this cozy and unique lakefront cottage is the perfect place for a relaxing couples getaway. Offering private access to Lake Scugog with an oversized dock for you to take advantage of water activities, enjoy your morning coffee and watch some of the best sunsets on the lake. The cottage sits only 15 min. from the quaint town of Port Perry where you can go to enjoy its brewery, incredible cuisine, farmers markets, and picturesque Main Street.

4.94 out of 5 average rating, 142 reviews

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

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.

Superhost

A spacious wooden dock extends over the calm waters of Lake Couchiching, featuring two white Muskoka chairs positioned for relaxing views. The serene landscape includes small islands visible in the distance under a bright blue sky with scattered clouds.

4.79 out of 5 average rating, 260 reviews

The Islandview

Welcome to The Islandview! Located on the sandy shores of Lake Couchiching, this gorgeous 4 season, 2-story open concept cottage is the perfect getaway. Escape to the private sun filled deck or dock on the water. Entertain in the open concept kitchen, two large living areas, or outdoors around the fire. During the day, enjoy watching the kids swim on the beach and at night take in the breathtaking sunsets. 5min to Washago & 10min to Casino Rama. Fully equipped with everything you need!

4.92 out of 5 average rating, 106 reviews

The living room features wooden walls and beams with ample natural light from a large window. A grand piano is positioned next to a cozy armchair, complemented by a clock above a stone fireplace. A colorful rug adds a touch of warmth to the space.

Cottage in Brechin

Cottage on Lake Simcoe Amazing lake Views

Lakefront 3-bedroom cottage on Lake Simcoe – perfect for families! . Please note You can see the lake from living room. Features a fully equipped kitchen and two 3-piece washrooms .Enjoy stunning lake views, BBQ, fishing, and crystal-clear shallow water safe for swimming (weather permitting). Apple picking in Fall and icing fishing in winter! Water access and beach area are shared with a few friendly neighbors. Fast starlink internet! Owner Allergic issue ,so please NO PET allowed.

A spacious cottage is set against a lush green backdrop, featuring a distinct barrel sauna nearby. A manicured lawn hosts a small putting green with flags, alongside several lounge chairs. The architecture blends modern and natural elements, creating an inviting outdoor environment.

4.96 out of 5 average rating, 104 reviews

Cottage w/sauna/games room/golf/|kayaks/beach

Welcome to Hally’s Cove Riverside Retreat 🌊⛵ A fully loaded 4-season escape on the Trent Severn Waterway! Dock your boat with shore power ⚓, lounge in the over-the-water hammock 🌅, relax in the panoramic sauna 🧖‍♀️, or play in the games room 🕹️ (ping pong, basketball, air hockey plus lots more). Enjoy the 4-hole putting green ⛳, 6 kayaks 🛶, lily pad and custom landscaped Muskoka rock fire pit 🔥. Bonus - Mosquito-reduced for extra comfort! IG to see more photos: @hallys_cove

4.77 out of 5 average rating, 191 reviews

A spacious outdoor area features a picnic table and fire pit, surrounded by lush green grass and trees. The serene view extends to the canal, with glimpses of nearby cottages, creating a peaceful setting ideal for outdoor relaxation.

Cabin in Severn Bridge

Moon River Place Unit 4A

A modest riverfront cottage with a full kitchen and bathroom, three bedrooms that sleeps six; 1 queen, 1 double and a bunk. 20 mins from Orillia, and 15 mins from Gravenhurst. Situated on a lively canal connecting Sparrow lake and lake Couchiching with private access. Perfect for families or small groups looking to enjoy some time away from the noise of the city. Please read the listing details, if you miss important information, please do not make a complaint about it later.

4.99 out of 5 average rating, 180 reviews

A serene outdoor space is captured, featuring a wooden dock adjacent to calm waters. Bright yellow adirondack chairs and a green umbrella enhance the area. Lush trees provide natural shade, creating a peaceful backdrop for relaxation or outdoor activities.

Guest suite in Washago

Spacious Apartment Facing The Severn River

Clean, lower unit, private entrance, one bedroom apartment fronting on the Severn River (aka Black). 90 mins. north of GTA. Five min. off Hwy 11 at the village of Washago where you can find most amenities. Fair weather activities include swimming, kayaking, canoeing, fishing or just dock time. Available winter months for simple relaxing accommodation. Hosts live on the upper floor and will be available to assist but will respect your privacy.

4.98 out of 5 average rating, 129 reviews

A bright, open space is revealed with large glass doors showcasing views of the lake. Minimalist furniture is arranged, including a light-colored sofa and a sleek dining table. Natural light floods in through the wood-beamed ceiling, enhancing the relaxed atmosphere.

Cottage in Brechin

Nordic Spa- Sauna: Spring Getaway

*** AMAZING WINTER PROMO: BOOK 2 NIGHTS and get the third free ( for winter travel to up to March 6) Your own private Nordic Spa !! Wood fired hot tub + sauna and Cold Plunge ! 1 hour and 20 mins from Toronto. 75 Feet of waterfront with the cottage being 18 feet from the edge of the lake. It is an incredible property to enjoy everything Lake Simcoe has to offer in the summer and winter ! Close to Orilla, ski hills and amazing ice fishing.

4.95 out of 5 average rating, 136 reviews

Riverfront Cottage with HotTub

Escape to our beautiful family owned and loved picturesque and serene waterfront cottage and wrap around deck with HotTub. With over 140 feet of private shoreline directly on the Black River offering 3 bedrooms, 4 beds, 2 full bathrooms, gas fireplace, a/c and central heating. Perfect winter getaway for couples and families, 90 minutes from Toronto, 15 minutes to Orillia. 3 Kayaks included. Fully equipped kitchen, fire pit and BBQ.