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Cumberland Beach Holiday Rentals

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Our top choices for Cumberland Beach holiday rentals

1. Lake View Loft Studio type

Lake View Loft Studio type
Severn
7.8 out of 10, Good, (6 reviews)
"The loft is spacious and well set up with quality furnishings and amenities. We were travelling further north the next day so it was convenient to the highway yet in a peaceful lakeside cottage setting."
Canada
Jason
The price is NZ$338
includes taxes & fees
8 Sept - 9 Sept
Lake View Loft Studio type

2. Lakefront Living Downtown Orillia.

Lakefront Living Downtown Orillia.
Orillia
9.2 out of 10, Wonderful, (13 reviews)
"Close to trails and downtown"
Canada
Frank
The price is NZ$385
includes taxes & fees
11 Aug - 12 Aug
Lakefront Living Downtown Orillia.

3. Bonnie 2 Cottage/Resort/Orillia, Muskoka

Bonnie 2 Cottage/Resort/Orillia, Muskoka
Washago
10.0 out of 10, Exceptional, (1 review)
"It was clean, and the property contacts were polite. The beds are a bit hard but better than nothing lol. The heat wasn’t working but it wasn’t too bad for us - we were given a space heater but I’m too nervous to use those overnight so we just used them while we were awake cause we happened to come during a curiously chilly rainy week. It is family friendly - the playground is a bit dated so my kids didn’t play on it cause they thought they would get slivers lol. The basketball net was well...
Canada
Ashley
The price is NZ$509
includes taxes & fees
7 Sept - 8 Sept
Bonnie 2 Cottage/Resort/Orillia, Muskoka

4. Magnificent Lakefront Modern Cottage

Magnificent Lakefront Modern Cottage
Washago
8.8 out of 10, Excellent, (26 reviews)
"Pros: Very helpful and responsive host. Nice lakefront property in a great location. Well furnished property 2 Kayaks included Amazing Ice Cream shop within walking distance (Scoops) Cons: The bedroom with the bunk bed gets much hotter than the other bedrooms One of the wooden planks on the dock is protruding and is a tripping hazard"
Canada
Gavin
The price is NZ$757
includes taxes & fees
7 Sept - 8 Sept
Magnificent Lakefront Modern Cottage

5. ❤ Cedar-View Studio with Hot Tub ❤

❤ Cedar-View Studio with Hot Tub ❤
Orillia
9.8 out of 10, Exceptional, (6 reviews)
"Perfect spot to stay for 2 in Orillia!"
United States
Rory P.
The price is NZ$386
includes taxes & fees
11 Aug - 12 Aug
❤ Cedar-View Studio with Hot Tub ❤

6. Modern Luxury Retreat with Stunning Views & Open Concept Design

Modern Luxury Retreat with Stunning Views & Open Concept Design
severn
10.0 out of 10, Exceptional, (3 reviews)
"Amazing stay for a girls getaway weekend!"
Canada
Angue
The price is NZ$1,333
includes taxes & fees
1 Sept - 2 Sept
Modern Luxury Retreat with Stunning Views & Open Concept Design

7. Beautiful Waterfront Cottage with Hot Tub in South Muskoka

Beautiful Waterfront Cottage with Hot Tub in South Muskoka
Severn Bridge
9.8 out of 10, Exceptional, (9 reviews)
"We had an enjoyable weekend staying at this charming cottage, which was spotless and well-maintained. The host was very responsive and easy to communicate with, making our experience even more pleasant."
United States
Maria Novamil B.
The price is NZ$1,003
includes taxes & fees
16 Aug - 17 Aug
Beautiful Waterfront Cottage with Hot Tub in South Muskoka

8. Log Cabin On the Lake B&B

Log Cabin On the Lake B&B
Kilworthy
9.8 out of 10, Exceptional, (45 reviews)
"We look forward to returning"
United States
Eric O.
The price is NZ$492
includes taxes & fees
16 Aug - 17 Aug
Log Cabin On the Lake B&B

9. Luxury Waterfront Cottage with Hot Tub in Downtown Washago, Ontario

Luxury Waterfront Cottage with Hot Tub in Downtown Washago, Ontario
Washago
8.2 out of 10, Very good, (11 reviews)
"Great place for a relaxing getaway! "
Canada
Sarah S.
The price is NZ$1,355
includes taxes & fees
13 Aug - 14 Aug
Luxury Waterfront Cottage with Hot Tub in Downtown Washago, Ontario

10. Campfire, Privacy, Stargazing minutes to Beaches/Orillia/Casino Rama

Campfire, Privacy, Stargazing minutes to Beaches/Orillia/Casino Rama
Orillia
10.0 out of 10, Exceptional, (2 reviews)
"This property was amazing. Super clean, well stocked, comfy beds, great air conditioning, and quiet area. Will definitely come back again!!"
United States
jacob m.
The price is NZ$615
includes taxes & fees
11 Aug - 12 Aug
Campfire, Privacy, Stargazing minutes to Beaches/Orillia/Casino Rama

11. Tamarack Marina Waterfront Suite with Marina Views. Sauna Included!

Tamarack Marina Waterfront Suite with Marina Views. Sauna Included!
Coldwater
The price is NZ$587
includes taxes & fees
31 Aug - 1 Sept
Tamarack Marina Waterfront Suite with Marina Views. Sauna Included!

12. Modern, fully renovated Studio!

Modern, fully renovated Studio!
Shanty Bay
10.0 out of 10, Exceptional, (1 review)
"Host was great and room was lovely"
Canada
Cassy W.
The price is NZ$278
includes taxes & fees
31 Aug - 1 Sept
Modern, fully renovated Studio!

13. 1 Bedroom Cottage VIII: PL

1 Bedroom Cottage VIII: PL
Gravenhurst
The price is NZ$427
includes taxes & fees
19 Aug - 20 Aug
1 Bedroom Cottage VIII: PL

14. Lovely Getaway in Nature

Lovely Getaway in Nature
Shanty Bay
7.6 out of 10, Good, (9 reviews)
"Pool, Hot Tub, Sauna and Gym were great!"
Canada
Melinda
Lovely Getaway in Nature

15. Off-Grid Getaway | Fireplace, BBQ & Patio

Off-Grid Getaway | Fireplace, BBQ & Patio
Gravenhurst
10.0 out of 10, Exceptional, (4 reviews)
"Really cute, clean and close to town and things to do."
United States
Jayne B.
The price is NZ$395
includes taxes & fees
31 Aug - 1 Sept
Off-Grid Getaway | Fireplace, BBQ & Patio

16. Charming Lakefront Cottage with Sauna, Fire Table & Sunset Views

Charming Lakefront Cottage with Sauna, Fire Table & Sunset Views
Sebright
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful property, responsive host, everything exactly as described."
United States
Danielle L.
The price is NZ$612
includes taxes & fees
7 Sept - 8 Sept
Charming Lakefront Cottage with Sauna, Fire Table & Sunset Views

17. Hillside Haven: Serene Studio Retreat for 4

Hillside Haven: Serene Studio Retreat for 4
Oro-Medonte
9.2 out of 10, Wonderful, (5 reviews)
"Terrific stay at Hillside Haven, all of the check in, parking and checkout details were communicated clearly. The unit is well maintained and the location is great being right next to the hills and the spa. "
Canada
Natasha S.
The price is NZ$264
includes taxes & fees
11 Aug - 12 Aug
Hillside Haven: Serene Studio Retreat for 4

18. Jacuzzi Suite Relaxing Retreat

Jacuzzi Suite Relaxing Retreat
Shanty Bay
9.4 out of 10, Exceptional, (26 reviews)
"The host was very accommodating and the place was very nice and exactly as described! Check in was easy and nicely laid out. "
Canada
Amanda
The price is NZ$333
includes taxes & fees
31 Aug - 1 Sept
Jacuzzi Suite Relaxing Retreat

19. Cozy 1-Bedroom Romantic Retreat with full Kitchen

Cozy 1-Bedroom Romantic Retreat with full Kitchen
Oro-Medonte
10.0 out of 10, Exceptional, (1 review)
"What a wonderful place to stay! The hose was so welcoming from the first communication and throughout the trip. The property was exactly as described but maybe even nicer in person than the pictures. The condo was super spacious with loads of room in the main room plus the bedroom. And the bathroom! Wow! Definitely spa-like with a seperate tub and shower. Treasure is comfortable to hang out on. Instructions inside for pool and wifi were clear. The bed was super comfy! And the black out curtains...
United States
Rayissa N.
The price is NZ$299
includes taxes & fees
11 Aug - 12 Aug
Cozy 1-Bedroom Romantic Retreat with full Kitchen

20. Country Retreat Horseshoe Valley

Country Retreat Horseshoe Valley
Shanty Bay
9.2 out of 10, Wonderful, (5 reviews)
"Great getaway in a quiet setting above Horseshoe Valley Resort. "
United States
David P.
The price is NZ$294
includes taxes & fees
11 Aug - 12 Aug
Country Retreat Horseshoe Valley
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.
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Top Cumberland Beach Hotel Reviews

Find out more about Cumberland Beach

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Cumberland Beach holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Cumberland Beach. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Cumberland Beach. Seeing all the best attractions is bound to make you fall in love with Cumberland Beach. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Cumberland Beach short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Cumberland Beach?

Yes, there are holiday rentals close to the most popular sights in Cumberland Beach, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Cumberland Beach has to offer?

Modern Luxury Retreat with Stunning Views & Open Concept Design: This holiday home rental outside of Cumberland Beach offers a patio, a selection of games and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Cumberland Beach?

With 4 Expedia holiday rentals, you're guaranteed to find just the right place for your Cumberland Beach stay.

What’s there to see and do in Cumberland Beach?

Get outdoors into nature at a spot like Lake Couchiching, or visit other top attractions such as Casino Rama. In the wider area, you’ll find Couchiching Beach Park and Orillia Opera House.

What’s a holiday rental in Cumberland Beach like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Cumberland Beach. Holiday rentals feature amenities such as hot tubs, fire pits and patios so you'll be comfy for your stay. If you're concerned about cleanliness, holiday rentals can offer a sense of seclusion away from shared hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for a family trip.