
Holiday rentals with outdoor seating in Midland
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Top-rated Holiday Houses with Outdoor Seating in Midland
Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.

RELAX @ our HOT TUB and SAUNA in the woods
PLEASE READ! Mt. St. Louis & Horseshoe Valley at doorstep! This is a bright, large and private walk-out GUEST SUITE (basement apartment). Hot tub, patio, fire pit & secluded path in the woods to enjoy nature. Kitchen is equipped with an induction cooktop and all things necessary, even wine bottle opener:) Open concept living room/kitchen/dining room with TV & Roku. Bedroom is a work of Art: dark, mysterious and romantic! Custom Queen bed made from weathered barn wood salvaged from our property.

Saltbox by the Bay | Vetta/Tay Shore Trail/Bikes
*GUEST BIKES AVAILABLE* Welcome to Saltbox by the Bay, your 4-season escape. A perfect couple's getaway or small family, friends or solo retreat. This vintage cottage is upcycled with luxe amenities. Make delicious meals, play records & boardgames & watch sunsets over the bay. Explore the treats of cottage country: walk or bike the Tay Shore Trail, visit Quayle's Brewery & Wye Marsh, pamper yourself at Vetta Nordic Spa & enjoy one of the nearby towns for beaches, restaurants & local amenities.

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

White Rolling Sands of Penetang by Theatre
Shores of Georgian Bay - enjoy a firepit in the backyard of a deep lot backing onto woods with trails. Local walking and cycling routes, vege and flower gardens from private sunny back deck. Fully licensed and located close to Kings' Wharf Theatre / Discovery Harbour. Experience the natural beauty of Tiny Beaches, Georgian Bay Islands N.P and Awenda P.P. nearby (Park pass available for use). Marinas, beaches, boat cruise of the islands, Ste Marie Among the Hurons and Wye Marsh (Midland) nearby.

Loft By The Bay
Welcome to our charming second storey apartment in downtown Midland, Ontario. This cozy space features a bedroom, office with futon, full kitchen, bathroom, laundry, and a bright open concept living area. Enjoy easy access to local shops, restaurants, and attractions. Explore the picturesque waterfront and nearby hiking trails. Retreat to this comfortable and inviting apartment after a day of work or play. Book your stay today for a convenient, comfortable, and memorable experience in Midland.

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.

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-Frame in the Woods of GeorgianBay, Muskoka
Welcome to our A-frame in the heart of Georgian Bay, Ontario! Perfect for family escapes and relaxing couples weekends in Muskoka. This cozy retreat has three bedrooms and accommodates up to six guests. With Six Mile Lake and Whites Bay just a stroll away, indulge in serene swims or explore the local golfing, breweries, and skiing at Mount St. Louis. Immerse yourself in nature's embrace while relishing the comforts of our picturesque A-Frame home—a perfect family getaway for every season!

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

Hosted by Nous Midland
Small-town charm at its best! Our centrally located apartment is the perfect home base for your small-town adventures. We're minutes from the unique shops and restaurants in downtown Midland and the Midland Harbour. There is plenty to experience; attend a local festival, take in a tourism site, hop onto the Trans Canada Trail System with your bike or snowmobile, attend a show/concert at the Midland Cultural Centre, or snowshoe through the Wye Marsh.

HOME ON BAY
A tranquil, beautiful & cozy 4-bedroom home for families and friends getting together. Walking distance to lake, groceries, LCBO, pharmacy, pub and restaurant. Close to numerous resorts and parks for summer and winter fun. Spacious kitchen and backyard deck are fully equipped with all your needs. Guests will enjoy all the entertainments both inside and outside all year round.. Daily rate is for 8 guests or less. No parties nor smoking allowed.

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. License #STRTT-2025-008
Popular amenities for Midland outdoor seating rentals
Holiday House Rentals with Outdoor Seating

Welcoming Waterfront Cottage

2min walk to the beach & 20 min drive to Blue Mnt

Luxurious 4BDRM-King Bed-Barrie-near Snow Resorts

Paradise Point Steps from Georgian Bay Great WIFI

Luxury Guest House with Private Hot Tub and Trails

Home in Barrie - Minutes to RVH & Georgian College

Sauna*King Bed*Fireplace*SmartTV

Orillia TwnHse Oasis w King Bed
Apartment rentals with outdoor seating

Beautiful Riverside Country Apartment

Muskoka Get Away-Romance & Adventure Awaits !!!

The Muskoka River Chalet - The King's Den

Lovely one bedroom guest suite in the country

Modern Condo at Friday harbour/Pet Friendly

Church Hill Haven Bed & Breakfast Guest Suite #2

Blue Mountain Studio Retreat

The Chieftain Suite
Condo rentals with outdoor seating

Bright MCM 2 Bedroom Walk Up with Private Deck/BBQ

Lovely 3 Bedroom Condo with Stunning View and Pool

Lovely 2-bedroom at Friday Harbour

Cozy Studio Mountainside stay in Blue Mountains

Designer Condo with beautiful harbour view.

Lovely Open Concept Friday Harbor Resort Condo

Resort Condo in Friday Harbour

Snowbridge Escape at Blue
Quick stats about holiday rentals with outdoor seating in Midland
Total rentals
120 properties
Nightly prices starting at
$86 NZD before taxes and fees
Total number of reviews
4.4K reviews
Family-friendly rentals
90 properties are a good fit for families
Pet-friendly rentals
50 properties allow pets
Rentals with a pool
20 properties have a pool
Destinations to explore
- Greater Toronto and Hamilton Area Holiday rentals
- Greater Toronto Area Holiday rentals
- Mississauga Holiday rentals
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- Rentals with a washing machine and dryer Midland
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- Rentals with a kayak Midland
- Rentals with a hot tub Midland
- Rentals with a patio Midland
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- Rentals with a fire pit Midland
- Cottage rentals Midland
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- Family-friendly rentals Midland
- Rentals with a fireplace Midland
- Apartment rentals Midland
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- Rentals with pools Midland
- Rentals with an EV charger Midland
- Rentals with outdoor seating Simcoe County
- Rentals with outdoor seating Ontario
- Rentals with outdoor seating Canada
- Blue Mountain Village
- Horseshoe Resort
- Snow Valley Ski Resort
- Beaver Valley Ski Club
- Osler Bluff Ski Club
- Craigleith Ski Club
- Devil's Glen Country Club
- Rocky Crest Golf Club
- Port Carling Golf & Country Club
- The Georgian Peaks Club
- Lake Joseph Golf Club
- Mount St. Louis Moonstone
- The Club At Bond Head
- Muskoka Lakes Golf and Country Club
- Georgian Bay Islands National Park
- Muskoka Bay Resort
- Windermere Golf & Country Club
- Barrie Country Club
- The Georgian Bay Club
- Toronto Ski Club
- Alpine Ski Club
- Hawk Ridge Golf & Country Club
- Mansfield Ski Club
- Heritage Hills Golf Club