
Pet-friendly holiday rentals in Midland
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Top-rated pet-friendly home 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.

Cozy Winter Escape - Ski, Hike & Chill by the fire
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

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!

Oasis Spa w/ Private Sauna!
Welcome to Our Unique Group of Spa Getaway Suites at Friday Harbour Resort - The Oasis Spa Getaway Rejuvenate, Relax & Unwind with your own private in-suite Sauna and Stunning patio Bamboo Oasis with fire table and Weber BBQ overlooking the pool & hot tub Reconnect with your loved one in our most tropical & romantic suite with multiple fire elements and fully stocked chefs kitchen Professionally designed to take your breath away, a luxury experience to make memories that last a lifetime!

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.

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!

Woodland Muskoka Tiny House
Enjoy the sounds of nature when you stay in this unique tiny house. This 600 sq ft home is nestled amongst 10 acres of towering trees, granite rock and trails to explore. The tiny home will not feel so tiny once inside. With high ceilings, plenty of windows, and surprisingly spacious rooms - it is the perfect hideaway for those wanting to unplug in Muskoka. The three season, screened in porch invites you to enjoy your coffee (or wine!) in nature without being bothered by the mosquitos!

Pet-friendly, 1 BR condo in Horseshoe Valley
All-season Condominium in Horseshoe Valley. Spacious BR with ensuite. Living room with fireplace, dining space, sofa bed. Private balcony, kitchen with all the necessities. Walk to the new Vetta Nordic Spa. Skiing , golfing , hiking & biking trails, treetop trekking, restaurants, groceries- 5 min drive Barrie , Orillia , Wassaga beach are 20 min. drive( beach #3 is PET FRIENDLY) Please note: we are NOT able to accept cats!

Private 40 Acre Cottage with Hot Tub
Our two bedroom cabin + cubby (available in summers) by a scenic pond is a private getaway while close to the main road and many amenities. Private outdoor space includes hot tub, deck, fire pit, and walking trails. We have a barn with ping pong and foosball tables. We are 20 min to Barrie, 10 min to Midland, 20 min to Balm beach, Wasaga beach, Mt. St Louis and Horseshoe Valley resort.

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 pet-friendly home rentals
Pet-friendly house rentals

Large 4 Br - 4.5 Bathroom: 2 King beds/Sauna/games

All-Season Chalet Retreat | Sleeps 14 | Ski & Spa

Mountain Cedar Chalet! Across from The Village

Serene mountainside home with View/Shuttle Bus

River Luxe Muskoka 6BR 5BA w/ Hottub, Wifi 200mb+

Driftwood on 6th Heritage Downtown Collingwood

Beachy Blue Bay Cottage - licence #STRTT-2025-194

King Bed*Pool*Fireplace*BBQ*Smart TV
Pet-friendly home rentals with a pool

The Snowbridge Lookout on Monterra Golf Course

Farmhouse GUEST SUITE; Year round hot tub

The Parker Slopeside: Hot Tub + Mountain Views

Base of Blue Mountain, Modern Studio

Utopia villa and spa

Great kitchen, comfy beds, games, walk 2 village +

Blue Mountain Escape! Pool&HotTub. Walk to Village

Wifi, Free parking, Ski, Kitchen, Laundry, TV, BBQ
Private, pet-friendly home rentals

Kempenhaus- Lake Simcoe Cottage & Spa | HOT TUB

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

Waterfront 3 BR Cottage 4 Seasons Gravenhurst Heat

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

Muskoka Cottage Getaway with Sauna

Hidden Gem

Glass Dome - Sleep Under The Stars- Free Sundays

Charming riverside cottage, B&B license
When is the best time to visit Midland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $204 AUD | $183 AUD | $181 AUD | $192 AUD | $190 AUD | $279 AUD | $285 AUD | $314 AUD | $323 AUD | $247 AUD | $213 AUD | $234 AUD |
| Avg. temp | -7°C | -6°C | -1°C | 6°C | 12°C | 17°C | 20°C | 19°C | 15°C | 9°C | 3°C | -3°C |
Quick stats about holiday rentals that are pet-friendly in Midland

Total holiday rentals
Explore 70 holiday rentals in Midland

Nightly prices starting at
Midland holiday rentals start at $75 AUD per night before taxes and fees

Verified guest reviews
Over 2,740 verified reviews to help you choose

Family-friendly holiday rentals
50 properties offer extra space and kid-friendly amenities

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
70 of Midland holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Midland rentals

4.7 Average rating
Midland stays receive an average rating of 4.7 out of 5 from guests
Destinations to explore
- Greater Toronto and Hamilton Area Holiday rentals
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- Mont-Tremblant Holiday rentals
- Waterfront rentals Midland
- Rentals with a kayak Midland
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- Cabin rentals Midland
- Rentals with beach access Midland
- Family-friendly rentals Midland
- Rentals with a hot tub Midland
- Rentals with a fire pit Midland
- Beachfront rentals Midland
- Rentals with a patio Midland
- Rentals with a washing machine and dryer Midland
- Fitness-friendly rentals Midland
- Rentals with a fireplace Midland
- Rentals with pools Midland
- Rentals with an EV charger Midland
- Rentals with lake access Midland
- Cottage rentals Midland
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- House rentals Midland
- Pet-friendly rentals Simcoe County
- Pet-friendly rentals Ontario
- Pet-friendly rentals Canada
- Blue Mountain Village
- Snow Valley Ski Resort
- Beaver Valley Ski Club
- Mount St. Louis Moonstone
- Devil's Glen Country Club
- Osler Bluff Ski Club
- Craigleith Ski Club
- Rocky Crest Golf Club
- Port Carling Golf & Country Club
- Windermere Golf & Country Club
- The Georgian Peaks Club
- Muskoka Lakes Golf and Country Club
- The Club At Bond Head
- Muskoka Bay Resort
- Lake Joseph Golf Club
- The Georgian Bay Club
- Georgian Bay Islands National Park
- Barrie Country Club
- Toronto Ski Club
- Mansfield Ski Club
- Alpine Ski Club
- Hawk Ridge Golf & Country Club
- Horseshoe Adventure Park
- Springwater Golf Course




