Photo by Sophia Field

Cumberland Beach Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 29 - Aug 31
In two weeks
Sep 5 - Sep 7
In one month
Sep 19 - Sep 21
In two months
Oct 17 - Oct 19

Browse Select Cumberland Beach Vacation Homes

Our top choices for Cumberland Beach vacation homes

Modern Luxury Retreat with Stunning Views & Open Concept Design
3 bedrooms, desk, iron/ironing board, free WiFi

Modern Luxury Retreat with Stunning Views & Open Concept Design

10.0 out of 10, Exceptional, (2)
Modern Luxury Retreat with Stunning Views & Open Concept Design
Charming studio in beautiful Waubaushene with AC
Interior

Charming studio in beautiful Waubaushene with AC

The price is CA $80
CA $145 total
includes taxes & fees
Aug 24 - Aug 25
Charming studio in beautiful Waubaushene with AC
Studio-King Bed with Heated pool
Interior

Studio-King Bed with Heated pool

The price is CA $131
CA $248 total
includes taxes & fees
Aug 24 - Aug 25
Studio-King Bed with Heated pool
Cabin peace & rest on Georgian Bay Tay Trail, 1min walk to beach, dock & fishing
Exterior

Cabin peace & rest on Georgian Bay Tay Trail, 1min walk to beach, dock & fishing

10.0 out of 10, Exceptional, (2)
"Absolutely lovely area, and a beautiful property to match. The host was super friendly, kind and easygoing. My girlfriend and I had an absolute blast, and would definitely return!"
The price is CA $266
CA $376 total
includes taxes & fees
Aug 25 - Aug 26
Cabin peace & rest on Georgian Bay Tay Trail, 1min walk to beach, dock & fishing
Up to 40% SALE Near-Skiing-Mount Gorgeous Cottage
Property grounds

Up to 40% SALE Near-Skiing-Mount Gorgeous Cottage

9.8 out of 10, Exceptional, (6)
"This rental was very affordable with lots of beds. We enjoyed our stay and had plenty of room for a larger group."
The price is CA $131
CA $415 total
includes taxes & fees
Sep 17 - Sep 18
Up to 40% SALE Near-Skiing-Mount Gorgeous Cottage
Wildwood Hot Tub + Indoor/Outdoor Pool + Sauna + Game Room
Pool

Wildwood Hot Tub + Indoor/Outdoor Pool + Sauna + Game Room

10.0 out of 10, Exceptional, (3)
"This was the perfect place for an effortless vacation with our son and his family. It is one of the cleanest places we have stayed in. The two-suite set up gave us room to gather together and privacy when needed for the younger ones. Our hosts were quick to communicate and helpful with advice on where to go for a family friendly beach. Of course, the pool was a big hit and it is nice that it was so close.A nearby grocery had everything we needed.We all commented on how comfortable the beds were...
The price is CA $159
CA $399 total
includes taxes & fees
Sep 9 - Sep 10
Wildwood Hot Tub + Indoor/Outdoor Pool + Sauna + Game Room
The Captains Lake House
Interior

The Captains Lake House

10.0 out of 10, Exceptional, (2)
"Beautiful house and location, very clean and well maintained with all the amenities. Excellent host, very helpful and responsive. Would book again if/when will be in the area Thank you "
The price is CA $384
CA $851 total
includes taxes & fees
Sep 3 - Sep 4
The Captains Lake House
Goffatt Island-your private island 1+1 Bedroom Cabin 202
Outdoor banquet area

Goffatt Island-your private island 1+1 Bedroom Cabin 202

The price is CA $298
CA $383 total
includes taxes & fees
Aug 24 - Aug 25
Goffatt Island-your private island 1+1 Bedroom Cabin 202
Lakefront Living Downtown Orillia.
Exterior

Lakefront Living Downtown Orillia.

10.0 out of 10, Exceptional, (3)
"Our stay was amazing! Jesse was available and helpful! The view and access to trails was only across the small street."
The price is CA $166
CA $343 total
includes taxes & fees
Aug 24 - Aug 25
Lakefront Living Downtown Orillia.
Cozy Newly Built Orillia Lakeside 5 Bedroom House! 3 minutes walk to the lake!
Smart TV

Cozy Newly Built Orillia Lakeside 5 Bedroom House! 3 minutes walk to the lake!

7.8 out of 10, Good, (7)
"The house was lovely and clean. It is a new build so the backyard is not finished, but otherwise it was really nice. Property management was quick to respond to all our questions and very helpful. Would recommend. "
The price is CA $194
CA $445 total
includes taxes & fees
Sep 1 - Sep 2
Cozy Newly Built Orillia Lakeside 5 Bedroom House! 3 minutes walk to the lake!
Couple’s Romantic & Adventure Retreat on the water
Property grounds

Couple’s Romantic & Adventure Retreat on the water

The price is CA $350
CA $500 total
includes taxes & fees
Aug 22 - Aug 23
Couple’s Romantic & Adventure Retreat on the water
Stunning Muskoka Oak Bay Golf Course - Port Severn Townhouse sleeps 8 free wifi
Interior

Stunning Muskoka Oak Bay Golf Course - Port Severn Townhouse sleeps 8 free wifi

10.0 out of 10, Exceptional, (1)
"Amazing house in a awesome location ! Couldn't have asked for better :)Jennifer was a great host and provided us with everything we needed ... and more !!!"
The price is CA $455
CA $731 total
includes taxes & fees
Aug 24 - Aug 25
Stunning Muskoka Oak Bay Golf Course - Port Severn Townhouse sleeps 8 free wifi
❤ Getaway with an 8-seater Hot Tub ❤
Exterior

❤ Getaway with an 8-seater Hot Tub ❤

10.0 out of 10, Exceptional, (1)
"Spacious and comfortable stay"
The price is CA $1,050
CA $1,356 total
includes taxes & fees
Aug 24 - Aug 25
❤ Getaway with an 8-seater Hot Tub ❤
Oriluxstay-Cozy Condo Townhome Just Steps from the Water | Your Perfect Getaway
Pool

Oriluxstay-Cozy Condo Townhome Just Steps from the Water | Your Perfect Getaway

The price is CA $319
CA $606 total
includes taxes & fees
Sep 2 - Sep 3
Oriluxstay-Cozy Condo Townhome Just Steps from the Water | Your Perfect Getaway
Lakefront Cottage w/ Hot Tub, 30 Guests 8000 sq ft
Pool

Lakefront Cottage w/ Hot Tub, 30 Guests 8000 sq ft

The price is CA $1,900
CA $2,901 total
includes taxes & fees
Sep 1 - Sep 2
Lakefront Cottage w/ Hot Tub, 30 Guests 8000 sq ft
Entire Resort - Sparrow Lake
Outdoor dining

Entire Resort - Sparrow Lake

Entire Resort - Sparrow Lake
King Suite, Jacuzzi, Full Kitchen, Heated pool
Fridge, microwave, oven, stovetop

King Suite, Jacuzzi, Full Kitchen, Heated pool

The price is CA $131
CA $273 total
includes taxes & fees
Aug 24 - Aug 25
King Suite, Jacuzzi, Full Kitchen, Heated pool
Fairway Retreat At Muskoka Bay Resort | Sleeps 8
Exterior

Fairway Retreat At Muskoka Bay Resort | Sleeps 8

The price is CA $787
CA $1,151 total
includes taxes & fees
Aug 31 - Sep 1
Fairway Retreat At Muskoka Bay Resort | Sleeps 8
Studio with King Bed, Heated pool
Interior

Studio with King Bed, Heated pool

6.0 out of 10, (1)
"Very disappointed. The unit is very rundown and even though it was clean it was too run down to matter. The mattress is broken. "
The price is CA $131
CA $248 total
includes taxes & fees
Aug 29 - Aug 30
Studio with King Bed, Heated pool
Cozy Chalet near Snowy Escapes & Outdoor Fun
Interior

Cozy Chalet near Snowy Escapes & Outdoor Fun

The price is CA $226
CA $472 total
includes taxes & fees
Aug 24 - Aug 25
Cozy Chalet near Snowy Escapes & Outdoor Fun
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Cumberland Beach Hotel Reviews

Econo Lodge Orillia

Econo Lodge Orillia

10/10 Excellent
"Me and my friend came to stay for 3 days for boots and hearts! It was an easy drive back and forth to locations. The hotel was clean and comfy stay, we got along with the lady that worked the front desk! She was amazing to us. We will be coming back next year. "
carina 3-night trip
Posted 2 days ago
Econo Lodge Orillia