
Family-friendly holiday rentals in Midland
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Top-rated family-friendly rentals in Midland
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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.

The Haunted House Apt 301
As you pull into the driveway this 1885 Victorian towers above you, your mouth drops in awe of the size. Up the porch to enter a small front door, a dimly lit winding staircase creaks as you ascend to 3rd floor. Original architecture painted many times over oozes with history. 70 years ago the house was turned into apartments, unloved for many of those years, time has definately taken its tole, yet to the spirits within, their big old house still stands proud and distinguished in all its glory.

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.

Hillside Haven: Serene Studio Retreat for 4
Escape to the serene Carriage Club Resort Studio! Dive into our inviting swimming pool, gather 'round the firepit, or challenge friends to volleyball. Stay active in our modern gym, then explore nearby skiing and golf. Pamper yourself at Vetta SPA or hit mountain biking and hiking trails. Your cozy studio, with a king-size bed and pull-out sofa, sleeps 4 comfortably. Nestled in rolling hills, just a 15-minute drive from Bass Lake's sandy shores. Discover tranquility with a touch of adventure!

Saltbox by the Bay + Bikes/Vetta/Ski | 4-Seasons
Welcome to Saltbox by the Bay, your 4-season escape. Perfect for couples, a small family/friends getaway or solo retreat. This vintage cottage is upcycled with luxe amenities. Made for slow living, cook up a storm, play boardgames & classic albums & watching sunsets over the bay. Explore the treats & charms of cottage country: walk or bike the Tay Shore Trail, visit Quayle's Brewery, trek Wye Marsh, pamper yourself at Vetta Nordic Spa or stop by one of the nearby towns for dinner & bowling.

Cozy Deluxe Studio at Horseshoe Valley
Welcome to Horseshoe Valley, just 1.5 hrs north of Greater Toronto Area. It's a four-season wonder of nature with limitless access to lakes, rivers, trails, and rolling hills. Whether you aim to ski in snow-laden forests of pine, hit golf at one of eighteen golf courses, mountain bike or hike in several landscape trails, soak in the healing experience of Vetta Nordic spa, or simply relax at the tranquility of the area, this place is simply yours to enjoy!

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.

Nest By The Bay - Downtown Midland / Private Loft
Luxury, Comfort & Style. This one-of-a-kind rental, "Nest By The Bay", is located in Downtown Midland. Walk everywhere, park your car & enjoy what Midland has to offer. Midland Harbour is only minutes by foot. Live our lifestyle, enjoy our many festivals, professional theatre, artisans, culinary cuisine, seasonal events & so much more! See our other listing "Perch By The Bay", also at this same location. Listing not suitable for ages under 6.

Cozy Off-Grid Bunkie on a Horse Farm
Take time away to rejuvenate in nature in our cozy off-grid bunkie on our 25 acre property and horse farm. Our hidden slice of heaven is on outskirts of Orillia, 10 minutes from restaurants, shopping, outings and adventures! Ask us about our Horse Connection experience! Walk our trails, relax with a book, play outdoor games, head to the local beach or enjoy a campfire under the stars.

Unique Tiny Home
This is a unique space with great attention placed on details. I design and build unique livable spaces catered to the individual needs of my clients. I invite you to come experience high quality living in a modern tiny home and experience sustainable, affordable living in just 280 square ft.
Popular amenities for Midland family-friendly rentals
Family-friendly home rentals with a hot tub

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

Glamping Dome Riverview Utopia

Lakefront Cozy Cottage w Hot Tub!

Stunning Mountain View- Pool, Hot Tub, WalkToBlue

Luxury Guest House with Private Hot Tub and Trails

The Bay View Cottage w/hot tub

Wifi, Free parking, Ski, Kitchen, Laundry, TV, BBQ

Spacious Hideaway in Nature
Family- and pet-friendly home rentals

Private Loft w Sauna, Fireplace, Wi-Fi & Projector

Paradise Pines Cabin in Woodland Acres

HOME ON BAY

The Guesthouse on the North Shore Trail

The Cottage on Coldwater; where bay & trail meet.

Woodland Muskoka Tiny House

Tiny A-Frame near the Bruce Trail

Glass Dome - Sleep Under The Stars- Free Sundays
Family-friendly home rentals with a pool

Blue Mountain Getaway at North Creek Resort

Lovely 3 Bedroom Condo with Stunning View and Pool

3BR Sierra Scandi Chic - Closest to Village

Mackenzie Cottage

Blue Mountain Escape! Pool&HotTub. Walk to Village

Mountain Peaks Retreat - Shuttle to Blue, Pool

Blue Mountain Studio Retreat

Private 2BR Condo | 4 Beds+Pool+Resort
Quick stats about holiday rentals that are family-friendly in Midland
Total rentals
120 properties
Nightly prices starting at
£30 before taxes and fees
Total number of reviews
6K reviews
Pet-friendly rentals
50 properties allow pets
Rentals with a pool
10 properties have a pool
Rentals with dedicated workspaces
70 properties have a dedicated workspace
Destinations to explore
- Greater Toronto and Hamilton Area Holiday rentals
- Greater Toronto Area Holiday rentals
- Mississauga Holiday rentals
- Niagara Falls Holiday rentals
- Pittsburgh Holiday rentals
- Grand River Holiday rentals
- St. Catharines Holiday rentals
- Detroit Holiday rentals
- Northeast Ohio Holiday rentals
- Laurentides Holiday rentals
- Mont-Tremblant Holiday rentals
- Cleveland Holiday rentals
- Rentals with a hot tub Midland
- Pet-friendly rentals Midland
- Rentals with outdoor seating Midland
- Rentals with pools Midland
- House rentals Midland
- Flat rentals Midland
- Rentals with a washing machine and dryer Midland
- Fitness-friendly rentals Midland
- Rentals with a firepit Midland
- Rentals with a kayak Midland
- Rentals with beach access Midland
- Rentals with lake access Midland
- Beachfront rentals Midland
- Rentals with a fireplace Midland
- Cottage rentals Midland
- Waterfront rentals Midland
- Rentals with a patio Midland
- Rentals with an EV charger Midland
- Cabin rentals Midland
- Family-friendly rentals Simcoe County
- Family-friendly rentals Ontario
- Family-friendly rentals 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
- Alpine Ski Club
- Toronto Ski Club
- Hawk Ridge Golf & Country Club
- Mansfield Ski Club
- Heritage Hills Golf Club