A train with colorful Adirondack chairs lined up in front.

Cumberland Beach Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Cumberland Beach vacation rentals

A lakeside view with three lounge chairs, a small table, and a stone wall.

1. Lake View Loft Studio type

Lake View Loft Studio type
Severn
8.0 out of 10, Very good, (7 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
$203 nightly
The price is $230
Oct 20 - Oct 21
Total with taxes and fees
Lake View Loft Studio type
A swimming pool with a fenced deck area, surrounded by trees and a view of a lake.

2. Bonnie 2 Cottage/Resort/Orillia, Muskoka

Bonnie 2 Cottage/Resort/Orillia, Muskoka
Washago
9.0 out of 10, Wonderful, (2 reviews)
"Very nice and quiet place to relax. The pool was very clean with ample seating. The lake was across the road and so was the boat launch. I would definitely recommend this resort."
United States
Luis F.
$194 nightly
The price is $219
Oct 21 - Oct 22
Total with taxes and fees
Bonnie 2 Cottage/Resort/Orillia, Muskoka
A modern building with a brick facade, large windows, and a small front garden.

3. Lakefront Living Downtown Orillia.

Lakefront Living Downtown Orillia.
Orillia
9.0 out of 10, Wonderful, (19 reviews)
"Gorgeous view and very comfortable living space. Great location, could walk to eat and for entertainment on the main drag. Very clean and the host was really nice and gave some options for eating."
Canada
Michelle
$208 nightly
The price is $235
Sep 25 - Sep 26
Total with taxes and fees
Lakefront Living Downtown Orillia.
A room with a large window overlooking a lake, a glass table, two chairs, and a ceiling fan.

4. Magnificent Lakefront Modern Cottage

Magnificent Lakefront Modern Cottage
Washago
8.8 out of 10, Excellent, (29 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
$333 nightly
The price is $376
Oct 1 - Oct 2
Total with taxes and fees
Magnificent Lakefront Modern Cottage
A spacious living area with a large fireplace, a dark sectional sofa, and a staircase leading to an upper level.

5. 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
$486 nightly
The price is $549
Sep 25 - Sep 26
Total with taxes and fees
Modern Luxury Retreat with Stunning Views & Open Concept Design
A covered outdoor seating area with a glass table and chairs, overlooking a parking lot and greenery.

6. Bonnie 1 Cottage/Resort/Orillia, Muskoka

Bonnie 1 Cottage/Resort/Orillia, Muskoka
Washago
$271 nightly
The price is $306
Sep 27 - Sep 28
Total with taxes and fees
Bonnie 1 Cottage/Resort/Orillia, Muskoka
A wooden deck with lounge chairs and a slide over a body of water.

7. Beautiful Waterfront Cottage with Hot Tub in South Muskoka

Beautiful Waterfront Cottage with Hot Tub in South Muskoka
Severn Bridge
9.4 out of 10, Exceptional, (16 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.
$367 nightly
The price is $415
Oct 20 - Oct 21
Total with taxes and fees
Beautiful Waterfront Cottage with Hot Tub in South Muskoka
A wooden deck with a fireplace, a table, and two chairs.

8. 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.
$203 nightly
The price is $234
Sep 27 - Sep 28
Total with taxes and fees
Off-Grid Getaway | Fireplace, BBQ & Patio
A dock with boats, a covered area, and a forested shoreline.

9. Snowmobile-In Riverside Suite with Sauna, Marina, Sleeps 6!

Snowmobile-In Riverside Suite with Sauna, Marina, Sleeps 6!
Coldwater
Snowmobile-In Riverside Suite with Sauna, Marina, Sleeps 6!
A wooden log cabin with a porch, two Adirondack chairs, and a fire pit.

10. Log Cabin On the Lake B&B

Log Cabin On the Lake B&B
Kilworthy
9.8 out of 10, Exceptional, (46 reviews)
"We look forward to returning"
United States
Eric O.
$255 nightly
The price is $288
Oct 4 - Oct 5
Total with taxes and fees
Log Cabin On the Lake B&B
An aerial view of a resort with multiple swimming pools, outdoor seating areas, and a large building with a distinctive roof.

11. Lux Studio in Horseshoe Valley

Lux Studio in Horseshoe Valley
Oro
8.8 out of 10, Excellent, (3 reviews)
"Quiet location Pool was close by Community bbq Trails nearby Nice little apartment"
Canada
Sam
$153 nightly
The price is $166
Sep 27 - Sep 28
Total with taxes and fees
Lux Studio in Horseshoe Valley
A deck with outdoor furniture, a pergola, and a view of the backyard.

12. Kahshe House: Newly Reno'd Summer Retreat

Kahshe House: Newly Reno'd Summer Retreat
Gravenhurst
$304 nightly
The price is $343
Sep 28 - Sep 29
Total with taxes and fees
Kahshe House: Newly Reno'd Summer Retreat
A wooden boardwalk through a natural area with dense vegetation and a clear sky.

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

Up to 40% SALE Near-Skiing-Mount Gorgeous Cottage
Victoria Harbour
8.4 out of 10, Very good, (28 reviews)
"The place has everything you need for comfortable stay with clean big rooms and supplies. It is an Old Place with spacious and ample rooms. Doors needs some greasing and it would also help to have some light in the yard for evening. Overall experience was great."
Canada
Akhila
$276 nightly
The price is $312
Oct 5 - Oct 6
Total with taxes and fees
Up to 40% SALE Near-Skiing-Mount Gorgeous Cottage
A balcony with wicker furniture, a red umbrella, and a view of a lake.

14. 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, (4 reviews)
"It's the perfect cottage and the most hospitable, helpful, kind hosts! Thank you for a fantastic weekend getaway!"
Canada
Netila
$296 nightly
The price is $335
Oct 5 - Oct 6
Total with taxes and fees
Charming Lakefront Cottage with Sauna, Fire Table & Sunset Views
An indoor swimming pool with clear glass walls, a separate hot tub area, and lounge chairs along the side.

15. 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.
$167 nightly
The price is $170
Oct 8 - Oct 9
Total with taxes and fees
Cozy 1-Bedroom Romantic Retreat with full Kitchen
A cabin with a dock, two Adirondack chairs, and a view of a lake.

16. 1 Bedroom Cottage VI: PL

1 Bedroom Cottage VI: PL
Gravenhurst
$226 nightly
The price is $256
Oct 1 - Oct 2
Total with taxes and fees
1 Bedroom Cottage VI: PL
A resort with a large pool, outdoor seating, and a modern building with a glass facade.

17. Hillside Haven: Serene Studio Retreat for 4

Hillside Haven: Serene Studio Retreat for 4
Oro-Medonte
9.0 out of 10, Wonderful, (6 reviews)
"Clean room and had all amenities we were looking for!"
Canada
Roxanne
$138 nightly
The price is $140
Sep 27 - Sep 28
Total with taxes and fees
Hillside Haven: Serene Studio Retreat for 4
A two-story house with a covered porch and a staircase leading to a deck.

18. Waterfront Cottage with Hot Tub

Waterfront Cottage with Hot Tub
Severn
9.0 out of 10, Wonderful, (29 reviews)
"Beautiful, water- side property perfect for families with kids of all ages. "
Canada
Adrianna K.
$365 nightly
The price is $412
Sep 25 - Sep 26
Total with taxes and fees
Waterfront Cottage with Hot Tub
A tent-like structure with a mattress inside, surrounded by a wooden frame and illuminated by string lights.

19. ❤ Cedar-View Apartment with Hot Tub (3 Bedrooms) ❤

❤ Cedar-View Apartment with Hot Tub (3 Bedrooms) ❤
Orillia
10.0 out of 10, Exceptional, (3 reviews)
"This property is located in a great area in orillia with a short drive to everything near by including the casino. The vibe in the home is homie and great for what you need for a one night or few night stay. Appreciated that they had the home stocked with small things like tooth brushes, paste, cookwear, etc. overall great stay would definitely come back!"
Canada
jasmine
$396 nightly
The price is $447
Sep 25 - Sep 26
Total with taxes and fees
❤ Cedar-View Apartment with Hot Tub (3 Bedrooms) ❤
A cabin with a wooden deck and a metal roof, surrounded by trees.

20. Charcoal Tree House: Cozy Cottage, Luxe Deck, Stargazing, Theatre, Forest Views

Charcoal Tree House: Cozy Cottage, Luxe Deck, Stargazing, Theatre, Forest Views
Gravenhurst
9.8 out of 10, Exceptional, (17 reviews)
"Excellent place to bring a family. Very clean and comfortable. Great forest views but close to the city if needed. Short commute to beaches. Great experience overall."
United States
Tabish k.
$430 nightly
The price is $495
Sep 27 - Sep 28
Total with taxes and fees
Charcoal Tree House: Cozy Cottage, Luxe Deck, Stargazing, Theatre, Forest Views
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.
View all properties
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

Pinedale Inn

Pinedale Inn

10/10 Excellent
"We stay at the Pinedale three times a year. We really enjoy it. It’s quiet, has incredible views from every room. It’s nice to have a full sized fridge and stove. It has a balcony and it’s close to downtown Gravenhurst. The outdoor pool is very nice and the staff are always friendly."
Sandra 3-night trip
Posted 8 hours ago
Pinedale Inn

Find out more about Cumberland Beach

Everything you need to know about Cumberland Beach vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Cumberland Beach vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cumberland Beach vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Cumberland Beach vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cumberland Beach. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Cumberland Beach in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $140 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Cumberland Beach rentals

At Expedia, we put the best Cumberland Beach vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Cumberland Beach rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cumberland Beach vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cumberland Beach. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Cumberland Beach?

Yes, there are vacation rentals near top local attractions in Cumberland Beach, or you can select a more secluded option if you're looking for relaxation.

What's the top vacation rental that Cumberland Beach has to offer?

WATERFRONT COTTAGE in Muskoka: You might want to consider this vacation home rental near Cumberland Beach, which is located on the waterfront and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals are there in Cumberland Beach?

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

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

While you're exploring the area, Lake Couchiching and Couchiching Beach Park are a couple of picturesque spots to get outside and enjoy nature. In the larger area, you’ll find Casino Rama and Orillia Opera House.

What’s a vacation rental in Cumberland Beach like?

Vacation rentals are privately owned properties where you can stay for a few weeks or just a few days in Cumberland Beach. Vacation rentals provide amenities like kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about cleanliness, vacation rentals can provide a sense of safety away from shared hotel elevators and busy front desks while still allowing you to travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for family trips or small group gatherings.