
House holiday rentals in Midland
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Top-rated house rentals in Midland
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Sawdust city haus
Bringing it back to our roots. This 800 sq/ft home from the 50’s has undergone major renovations with you in mind. Located steps from Lake Muskoka, a short drive to the Gravenhurst wharf, an even shorter drive to town & Dr Bethune; just the beginning of what this home has to offer. Enjoy walking trails, a boat launch with private mooring space, sawdust city brewery, the oar restaurant, Muskoka boat rentals, steamship tours, parasailing, local events, etc. all from the privacy of a dead end road.

Our vacation home. Fully equipped. Pool. Fire Pit.
Stylish. Privacy. Location. Our Vacation Home, is in vibrant Downtown Midland. We’ve recently renovated our amazing century home and it is ready for you to enjoy! – its beauty matches the beauty of the town. Our spacious home features a great backyard for you to relax in. When venturing out to explore the area we know you’ll enjoy Midland Harbour. This picturesque natural attraction has been a favourite of tourists and boaters from around the world. Our home is just a few minutes’ walk away!

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.

Orillia TwnHse Oasis w King Bed
Have fun with the whole family at this stylish townhouse oasis. The townhouse features 3 bedrooms, 2.5 bathrooms and 4 beds. The principle bedroom has a king bed, the 2nd bedroom has a queen bed, and the third bedroom has a queen bunk bed (qn bttm, qn top). The house features a large deck with a gas bbq, outdoor dining, and lots of lounging space. Right behind the townhouse is a beautiful nature ravine with lots of trails. Come, enjoy and relax. The property offers super high speed internet.

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!

JJ’s small town country retreat
Take a step back in time to this old farm house. Located on the corner of our little town called Badjeros. This house was built in the 1930s and it’s been in our family for over 80 years. Since then there has been numerous upgrades to the house as well as a large 1200 square foot open concept addition built onto the existing house. While out in the country, this house is central to many attractions in the area 1.5 hours south of Toronto/GTA. Blue Mountain/ Collingwood is 30 minutes north.

Muskoka Hideaway-hot tub/private trails/wood stove
Hidden amongst the trees in the middle of Muskoka, this Hemlock log cabin boasts high ceilings and a true "cabin in the woods" feel. Its not hard to relax and unwind with a coffee in front of the fire, or go and explore along the private forest trails (1-2k of walking trails). As well, downtown Bracebridge is a convenient 10 minute drive away with all amenities. There is a veggie garden on the property and depending when you come you can pick away at it :) Pets are welcome in the home!

Georgian Bay Paradise
Enjoy a relaxing vacation away from the hustle & bustle in this delightful 3 bedroom waterfront cottage. Just 90 minutes north of Toronto, this newly-renovated, gorgeous retreat is right on Georgian Bay, one of the world's most sought after destinations. Revel in breathtaking views, amazing sunsets and the privacy of numerous cedars. You will love the sun, sand, rock and waves which will captivate you. Access your own deck, lawn, and beach as well as many fun winter activities.

Spacious Barrie Basement with Separate Entrance
This newly renovated 2-bedroom basement is bright and spacious, it offers a kitchenette, a bathroom, two bedrooms and laundry. Wifi/Bedding/Towels/Dishes/Bath Accessories/Free parking spot on our driveway and free street parking (ONLY Available Apr-Dec). This is a great choice for your family summer/winter vacation! A few minutes' drive to downtown Barrie and beautiful Lake Simcoe waterfront, various restaurants, Costco, Walmart and unique shops.

100% Private 1-Bdrm+Fireplace. Quiet+comfortable.
Welcome to our recently renovated unit, nestled on a quiet, residential street. This bright, 100% private basement unit offers the perfect blend of comfort and convenience. Stylishly decorated, it combines contemporary style with warm home comforts. Expect a tranquil haven where you can relax and unwind, but still remain close to the action. We're a 5-minute drive to downtown & a 10-minute drive to Blue Mountain.

Home in Barrie - Minutes to RVH & Georgian College
Minutes from RVH Hospital, Georgian College, Hwy 400, and the Barrie Waterfront. Clean, newly renovated, main floor of home in a quiet neighborhood. Your family will be close to everything when you stay at this centrally located place. Brand new tv in every room. Air mattress available by request. PLEASE inform us if you would like to use the couch as a bed so we can provide you extra linen. Thank you ☺️
Popular amenities for house rentals in Midland
House rentals with a pool

The Cozy Corner Townhome - Shuttle to the Village

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

King Bed, Pool, Gym, Ravine View, Your Getaway!

Rivergrass Oasis: Across from Blue Mtn | Hot Tub!

Blue Mountain Retreat In Historic Snowbridge

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

Serene mountainside home with View/Shuttle Bus

Luxury Resort Villa on Muskoka Bay Golf Course
Weekly house rentals

Entire Unit, clean and Private 1 bdr

New home|LAKE FRONT|Hot tub|20ft ceilings

River's End: Explore the river by kayak or canoe!

Gleaming Family Friendly Vacation Home Near Beach

Private log cottage on 2 acres

The Allandale Residence

Blue Water Dunes Cottage

Bright Modern Retreat in Barrie
Private house rentals

Family-Size Nottawa Loft 3BR

SuperHost BNB ~ Blue Mountain~ Scandinavian Spa

2 Bd Boardwalk Condo Patio Oasis

New renovated cozy and clean

3BR Spacious Home - KING BED

Stylish & Renovated 3bdr home in Barrie

Your Bala home away from home

Comfort, Luxury and Relaxation
When is the best time to visit Midland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $219 SGD | $182 SGD | $208 SGD | $212 SGD | $233 SGD | $256 SGD | $306 SGD | $290 SGD | $292 SGD | $249 SGD | $247 SGD | $267 SGD |
| 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 house rentals in Midland

Total holiday rentals
Explore 60 holiday rentals in Midland

Nightly prices starting at
Midland holiday rentals start at $26 SGD per night before taxes and fees

Verified guest reviews
Over 1,920 verified reviews to help you choose

Family-friendly holiday rentals
50 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
60 of Midland holiday 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
Destinations to explore
- Greater Toronto and Hamilton Area Holiday rentals
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- Rentals with lake access Midland
- Cottage rentals Midland
- Beachfront rentals Midland
- Rentals with outdoor seating Midland
- Waterfront rentals Midland
- Fitness-friendly rentals Midland
- Rentals with beach access Midland
- Rentals with pools Midland
- Rentals with a patio Midland
- Cabin rentals Midland
- Rentals with a washing machine and dryer Midland
- Family-friendly rentals Midland
- Rentals with a fireplace Midland
- Flat rentals Midland
- Rentals with an EV charger Midland
- Rentals with a hot tub Midland
- Rentals with a kayak Midland
- Pet-friendly rentals Midland
- Rentals with a firepit Midland
- House rentals Simcoe County
- House rentals Ontario
- House rentals Canada
- Blue Mountain Village
- Snow Valley Ski Resort
- Beaver Valley Ski Club
- Devil's Glen Country Club
- Osler Bluff Ski Club
- Craigleith Ski Club
- Mount St. Louis Moonstone
- Rocky Crest Golf Club
- Port Carling Golf & Country Club
- Windermere Golf & Country Club
- The Georgian Peaks Club
- The Club At Bond Head
- Muskoka Lakes Golf and Country Club
- Muskoka Bay Resort
- Lake Joseph Golf Club
- The Georgian Bay Club
- Georgian Bay Islands National Park
- Barrie Country Club
- Alpine Ski Club
- Toronto Ski Club
- Hawk Ridge Golf & Country Club
- Mansfield Ski Club
- Heritage Hills Golf Club
- Springwater Golf Course




