
Pet-friendly vacation rentals in Midland
Find and book unique pet-friendly homes on Airbnb
Top-rated pet-friendly home rentals in Midland
Guests agree: these pet-friendly homes 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.

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

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.

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.

The Cottage on Coldwater; where bay & trail meet.
Georgian Bay on one side and the Tay Trail on the other, this lakeside cottage offers gifts for all seasons. With spectacular views of the bay ready 4 ice fishing, sledding, skiing and snow shoeing over winter; hiking, biking, boating and swimming over summer with infinite possibilities in between, we're sure Waubaushene will suit your needs. Close to quaint Coldwater stores, kilometers of Parks, a short drive to 2 ski hills and just off Hwy 400, this hidden gem can accommodate adventure.

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.

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.

Cozy & Private Guest Suite in Stayner, Ontario.
PLEASE READ THE DESCRIPTION In "The Space" BEFORE BOOKING. The space DOES NOT HAVE A SHOWER. We are a proud Superhost destination close to Wasaga Beach (15-20 mins), Collingwood (20-25 mins) and Blue Mountain Village (30-35 mins.) The place is super cozy. You'll love the location, the privacy, the amenities, the hosts and the value. This place is fabulous for couples, solo adventurers, business travellers, and canine companions. Also… THERE IS NO SHOWER

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.

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.

Cozy Beach Cottage with Pool | Georgian Bay
Georgian Bay Beach club. Cute cottage perfect for families, couples, or anyone wanting to relax! 2 bedrooms, 1 bathroom, furnished, pool and private beach on the shores of beautiful Georgian Bay in Tiny township. Cottage is part of a 12 cottage community that shares the pool and beach area. Always super clean, professionally cleaned after every guest! Note: pool is closed October to mid May.

Cozy 1-Bedroom Romantic Retreat with full Kitchen
Escape to Carriage Club Resort, nestled on rolling hills near Horseshoe Valley. Our 1-bedroom vacation rental sleeps 4 with a king-size bed and pull-out sofa. Enjoy the pool, firepit, volleyball, gym, and nearby skiing, golf, and Vetta SPA. Explore hiking trails, high ropes, and a 15-minute drive to Bass Lake's beach. Experience adventure and relaxation at Carriage Club!
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

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

JJ’s Collingwood bar & games house.
Pet-friendly home rentals with a pool

The Snowbridge Lookout on Monterra Golf Course

Farmhouse GUEST SUITE; Year round hot tub

Base of Blue Mountain, Modern Studio

The Parker Slopeside: Hot Tub + Mountain Views

Utopia villa and spa

Blue Mountain Escape! Pool&HotTub. Walk to Village

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

Private 2BR Condo | 4 Beds+Pool+Resort
Private, pet-friendly home rentals

A modern retreat on Georgian Bay STRTT-2026-089

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

The Beach House, Georgian Bay, Beach View w/ Sauna

Steps From the Beach and Hiking Trails!

Hidden Gem

Glass Dome - Sleep Under The Stars- Free Sundays

OakRidge Retreat-HOT TUB 100s of acres WIFI

Forest Harbour Hideaway
When is the best time to visit Midland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $186 CAD | $167 CAD | $165 CAD | $175 CAD | $174 CAD | $254 CAD | $260 CAD | $287 CAD | $295 CAD | $226 CAD | $194 CAD | $213 CAD |
| 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 vacation rentals that are pet-friendly in Midland

Total vacation rentals
Explore 70 vacation rentals in Midland

Nightly prices starting at
Midland vacation rentals start at $68 CAD per night before taxes and fees

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

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

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
70 of Midland vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Midland rentals

4.7 Average rating
Midland stays receive an average rating of 4.7 out of 5 from guests
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- 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
- Alpine Ski Club
- Mansfield Ski Club
- Hawk Ridge Golf & Country Club
- Horseshoe Adventure Park
- Springwater Golf Course




