
House holiday rentals in Midland
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Top-rated house rentals in Midland
Guests agree: These houses are highly rated for location, cleanliness and more.

Luxurious 4BDRM-King Bed-Barrie-near Snow Resorts
Our luxury home rental is located in one of the best neighborhoods in Barrie. Secluded neighborhood surrounded by forest. 5 min to HWY 400 8 min to Downtown Barrie 11 min to Snow Valley Ski resort 40 min to Blue Mountain & Wasaga Beach 25 min to Friday Harbor Resort Free WiFi-Cable & Parking Perfect home for families and large groups. Newly renovated home, with beautiful large outside area and swimming pool. Accommodates up to 9 guests. Pool open May 31 (Solar heated) Pool closes Sept.7

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!

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.

Waterfront home, city/sunset view & steps to beach
Waterfront w/ private dock. Renovated upscale home + new hot tub, full city bay views w/summer sunsets+sunrise. Steps to Minet's Point beach & park. 4 proper bdrms & 2 pull out couches(Queen & Twin) 3 full bthrms + sauna, over 2400+sqft. Prking for 3 cars, additnal prking available via lot beside. Gas BBQ, fire pit, 2x gas FP, fast Wifi & 77" TV, wshr/dryr. 48amp EV pwr. Minuts to Marina for Seadoo/boat rentals. Wlking distnce to fine dining/pubs & stores. Kite surf & ice fishing

JJ’s Collingwood bar & games house.
welcome to beautiful 4 season collingwood! This house offers a 3 bedroom 2 bathroom fully detached house on a large mature lot in collingwood. Less than 10minute walk to sunset point beach and a 10 minute walk to downtown collingwood. House is in a prime location approximately 10 minute drive to blue mountain, 20 minutes to Thornbury and 15 minute drive to Wasaga beach. Big fenced in backyard for fires, horse shoes or whatever you would like, plenty of parking ( 4 car maxim)

Muskoka River Cabin
Unique, A Frame, Custom built on three acres in the Heart of Muskoka. Enjoy your own dock on a quiet section of the Muskoka River. It's a perfect place to escape the city, enjoy some peace, reconnect with yourself and the ones you love. Breathe in some fresh air, enjoy the sounds of nature and do some star gazing right from the front deck. *Please note-all guests must have a minimum of two reviews to book*
Popular amenities for Midland house rentals
House rentals with a pool

Cute and Cozy House

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: Steps to Blue Mountain Village!

Blue Mountain Retreat In Historic Snowbridge

Serene mountainside home with View/Shuttle Bus

Family & Friends Retreat
Weekly house rentals

Cozy Home in Barrie

Farm House

Breezy Beach Vibes at Villa Tina

Gleaming Family Friendly Vacation Home Near Beach

Cozy Creek Side walkout basement.

The Allandale Residence

Victoria Harbor cottage

Georgian Bay Water/Beach front Cottage
Private house rentals

Family-Size Nottawa Loft 3BR

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

3BR Spacious Home - KING BED

[Casa Luna]Chic Lakehouse| BBQ|HotTub|LakeViews

Stylish & Renovated 3bdr home in Barrie

6 Bdrm Lake view, Luxury, Modern Cottage w Hot Tub

Upper Shadow Creek Haven - Waterfront

Dream Retreat: Relaxing Vacation
When is the best time to visit Midland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $297 NZD | $247 NZD | $283 NZD | $288 NZD | $316 NZD | $348 NZD | $415 NZD | $394 NZD | $396 NZD | $338 NZD | $336 NZD | $362 NZD |
| 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 $35 NZD 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 and kid-friendly amenities

Pet-friendly accommodation
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
60 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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- Beachfront rentals Midland
- Rentals with a fireplace Midland
- Rentals with a fire pit Midland
- Cabin rentals Midland
- Rentals with outdoor seating Midland
- Fitness-friendly rentals Midland
- Rentals with an EV charger Midland
- Rentals with lake access Midland
- Pet-friendly rentals Midland
- Cottage rentals Midland
- Rentals with a kayak Midland
- Rentals with pools Midland
- Rentals with a washing machine and dryer Midland
- Family-friendly rentals Midland
- Apartment rentals Midland
- Waterfront rentals Midland
- Rentals with a patio Midland
- Rentals with beach access Midland
- Rentals with a hot tub 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
- Rocky Crest Golf Club
- Port Carling Golf & Country Club
- Mount St. Louis Moonstone
- The Georgian Peaks Club
- Muskoka Lakes Golf and Country Club
- Muskoka Bay Resort
- The Club At Bond Head
- Lake Joseph Golf Club
- Windermere Golf & Country Club
- Georgian Bay Islands National Park
- The Georgian Bay Club
- Barrie Country Club
- Toronto Ski Club
- Alpine Ski Club
- Mansfield Ski Club
- Hawk Ridge Golf & Country Club
- Heritage Hills Golf Club
- Springwater Golf Course




