Our other sites
Get A Free World Heritage Guide »
SeatGuru
Family Vacation Critic
Cruise Critic
BookingBuddy
We recommend:
We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers: Windows: Internet Explorer, Mozilla Firefox. Mac: Safari.

Midland

Popular vacation rentals:

Explore the world! TripAdvisor has reviews and information on over 400,000 locations, including:
Vacation Rentals

Explore other Midland resources:

Midland Vacation Rentals

Hotels (7)

B&Bs / Inns (6)

Specialty Lodging (0)

Vacation Rentals (15)

The safest rental experience online

Rent from verified owners and managers, and read reviews before you book.

Find out what to expect »

In partnership with:

Get listed!

Add your property »

Other Destinations
Popular Ontario Destinations
Niagara Falls Vacation Rentals (1)
Ottawa Vacation Rentals (3)
Toronto Vacation Rentals (4)
Nearby listings
Amazing Hotel Alternative _Central Toronto Luxury, Toronto
Amazing Hotel Alternative _Central Toronto Luxury
    Price: €83/night €550/week
  • Bedrooms: 3, sleeps 6
  • Bathrooms: 2
    • Contact Owner
Downtown Penthouse 2BR/2BA Designer Furnished, Toronto
Downtown Penthouse 2BR/2BA Designer Furnished
    Price: €791 - €1,307/week €2,373/month
  • Bedrooms: 2, sleeps 4
  • Bathrooms: 2
  • Min stay: 7
    • Contact Owner
Downtown Apartment in Historic Cabbagetown, Toronto
Downtown Apartment in Historic Cabbagetown
    Price: €600/week €1,642/month
  • Bedrooms: 1, sleeps 6
  • Bathrooms: 1
    • Contact Owner
Modern Coach House, Toronto
Modern Coach House
    Price: €85/night €597/week €2,464/month
  • Bedrooms: 1, sleeps 2
  • Bathrooms: 1
    • Contact Owner
"Hoblet" nestled by the woods,5 patio doors,600sq, Niagara Falls
    Price: €85/night
  • Bedrooms: 2, sleeps 4
  • Bathrooms: 1
    • Contact Owner
LUXURY FURNISHED APARTMENT OTTAWA, Ottawa
LUXURY FURNISHED APARTMENT OTTAWA
    Price: €158/night €790/week €1,896/month
  • Bedrooms: 1, sleeps 2
  • Bathrooms: 1
    • Contact Owner
Pine Lake Retreat, Ottawa
Pine Lake Retreat
    Price: Inquire for rates
  • Bedrooms: 3, sleeps 8
  • Bathrooms: 3
    • Contact Manager
Cherry Hollow, Ottawa
Cherry Hollow
    Price: Inquire for rates
  • Bedrooms: 5, sleeps 12
  • Bathrooms: 3
    • Contact Manager

Search Midland Vacation Rentals

Clear dates

Advanced Search

Recommended by Travelers

[ Recommended ] [ Price / nt ] [ Price / wk ] [ Price / mo ] [ Bedrooms ]
Cobble Beach Cottage, Midland
Cobble Beach Cottage
Contact Manager
4 of 5 stars 1 review
Management: Professional
Property: Rental Home
Bedrooms: 3, sleeps 6
Bathrooms: 3
You'll get a sense that you are heading to a very special place as you enjoy breath taking views of Georgian Bay along the Scenic Route from Owen Sound. ...
  • Nightly
    --
  • Weekly
    --
  • Monthly
    --
Robin's Point, Midland
Robin's Point
Contact Manager
4.5 of 5 stars 3 reviews
Management: Professional
Property: Rental Home
Bedrooms: 3, sleeps 8
Bathrooms: 2
The best of every world - waterfront cottage living; modern amenities that include hi-speed internet; privacy; yet close enough to civilization to enjoy all ...
  • Nightly
    --
  • Weekly
    --
  • Monthly
    --
Balm Beach Stroll, Midland
Balm Beach Stroll
Contact Manager
3.5 of 5 stars 1 review
Management: Professional
Property: Rental Home
Bedrooms: 3, sleeps 6
Sometimes, all you want is a nice little cottage in which to relax and spend a week at the beach with the kids. Balm Beach stroll is exactly that. Located on ...
  • Nightly
    --
  • Weekly
    --
  • Monthly
    --
Discovery Villa, Midland
Discovery Villa
Contact Manager
3.5 of 5 stars 3 reviews
Management: Professional
Property: Rental Home
Bedrooms: 5, sleeps 10
Bathrooms: 3
This wonderful cottage is richly enhanced with wood and nautical touches, and has a great sand beach on Penetanguishene Bay. When we look for cottages to add ...
  • Nightly
    --
  • Weekly
    --
  • Monthly
    --
Doorian Gray cottage (#597), Midland
Doorian Gray cottage (#597)
Contact Manager
Management: Professional
Property: Rental Home
Bedrooms: 3, sleeps 6
Bathrooms: 1
Cottage Profile Hop, skip and a jump to a beautiful sandy beach! ‘DoorianGray’ is located north of Wasaga Beach and close to Balm Beach, this is an all-season ...
  • Nightly
    --
  • Weekly
    €1,032
  • Monthly
    --
Sawlog Serenity, Midland
Sawlog Serenity
Contact Manager
Management: Professional
Property: Rental Home
Bedrooms: 3, sleeps 6
Who said you had to break open the piggy bank to enjoy a cottage? With its cosy wood-paneled theme, the peaceful, relaxing outdoor sitting areas and the ...
  • Nightly
    --
  • Weekly
    --
  • Monthly
    --

The following rentals are within 25 miles of Midland, Ontario.

Georgian Sunset cottage (#576), Wasaga Beach
Georgian Sunset cottage (#576)
Contact Manager
4.5 of 5 stars 2 reviews
Management: Professional
Property: Rental Home
Bedrooms: 4, sleeps 8
Bathrooms: 2
Cottage Profile Wow! Sunsets and waterfront! Long panoramic views of the Blue Mountains and Christian Island over beautiful Nottawasaga Bay! Located north of ...
  • Nightly
    --
  • Weekly
    €619 - €1,307
  • Monthly
    --
Beach Trees, Penetanguishene
Beach Trees
Contact Manager
4 of 5 stars 1 review
Management: Professional
Property: Rental Home
Bedrooms: 3, sleeps 6
We’ve been looking for this one for a while, and it’s been worth the wait! Beach Trees has everything you want in a traditional cottage – a ...
  • Nightly
    --
  • Weekly
    --
  • Monthly
    --
Timber Lodge, Port Severn
Timber Lodge
Contact Manager
4.5 of 5 stars 2 reviews
Management: Professional
Property: Rental Home
Bedrooms: 5, sleeps 12
Living large takes on a double meaning at Timber Lodge. The size and amenity list of this wonderful Confederation Log Home on Six Mile Lake ensure that your ...
  • Nightly
    --
  • Weekly
    --
  • Monthly
    --
California Dreamin', Wasaga Beach
California Dreamin'
Contact Manager
4 of 5 stars 1 review
Management: Professional
Property: Rental Home
Bedrooms: 3, sleeps 7
If you want beachfront, you've come to the right place. This Malibu style, newly renovated waterfront beach house is located in a much desired, quiet area of ...
  • Nightly
    --
  • Weekly
    --
  • Monthly
    --
Chateau Champlain cottage (#553), Penetanguishene
Chateau Champlain cottage (#553)
Contact Manager
3.5 of 5 stars 2 reviews
Management: Professional
Property: Rental Home
Bedrooms: 1, sleeps 8
Cottage Profile Explore, discover and experience an original summer vacation on 120 feet of sandy shores of beautiful Penetanguishene Bay!! This is an opulent ...
  • Nightly
    --
  • Weekly
    €825 - €1,719
  • Monthly
    --
SummerSet cottage (#494), Wasaga Beach
SummerSet cottage (#494)
Contact Manager
Management: Professional
Property: Rental Home
Bedrooms: 2, sleeps 5
Bathrooms: 1
Policy: Smoking not allowed, Pets not allowed, Not handicap accessible Check-In: 4:30pm Check-Out: 10:30am
  • Nightly
    --
  • Weekly
    €619 - €928
  • Monthly
    --
Among These Branches, Penetanguishene
Among These Branches
Contact Manager
Management: Professional
Property: Rental Home
Bedrooms: 3, sleeps 6
We were delighted to be able to see the owners renovate this traditional Georgian Bay cottage. We think you'll be just as thrilled with the results as they ...
  • Nightly
    --
  • Weekly
    --
  • Monthly
    --
Severn Heaven, Coldwater
Severn Heaven
Contact Manager
Management: Professional
Property: Rental Home
Bedrooms: 3, sleeps 6
Bathrooms: 3
There are places on this Earth that are truly inspiring - that put you in awe of the natural world. Severn Heaven is one of those places. Located on Muskoka's ...
  • Nightly
    --
  • Weekly
    --
  • Monthly
    --
JP's Chalet, Wasaga Beach
JP's Chalet
Contact Manager
Management: Professional
Property: Rental Home
Bedrooms: 4, sleeps 8
Bathrooms: 3
We are very excited to have this property available on the pages of CLRM. If you want to experience Cottage Country without sacrificing the comforts of home, ...
  • Nightly
    --
  • Weekly
    --
  • Monthly
    --
Professionally managed typically means…
  • Member of the FlipKey Verified Property Manager program
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
  • Secure credit card payment
Verified Plus property owner typically means…
  • Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
  • Established history of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Verified property owner typically means…
  • Verification of owner name and address via valid credit card
  • History of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns