Cumberland Holiday Rentals

Start date: Check-in selected.
End date: Check-out
    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
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Holiday Rentals in Cumberland

Our top choices for Cumberland holiday rentals

The Weldon Hotel

4.5 star property
9.8 out of 10, Exceptional, (77)
"Absolutely beautiful place to stay. "
The price is AU$685
includes taxes & fees
14 Sept - 15 Sept
The Weldon Hotel

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

10.0 out of 10, Exceptional, (226)
"We had a wonderful stay at this cottage. Great location to explore the surrounding areas."
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.

2.0 star property
10.0 out of 10, Exceptional, (2)
"The property was as described, clean, and in a quiet neighborhood. Conveniently located to many local attractions. Check in and check out process was smooth. Overall enjoyed my stay very much. "
Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.

Camp Forever cottage

9.6 out of 10, Exceptional, (52)
"Great little getaway. Would recommend this place to others for sure."
The price is AU$431
includes taxes & fees
1 Oct - 2 Oct
Camp Forever cottage

Private Lakefront Estate with 180 Degree Views

10.0 out of 10, Exceptional, (6)
Private Lakefront Estate with 180 Degree Views

Studio Unit Walkable Everywhere

6.0 out of 10, (3)
"Great, comfortable place to stay. The location is super walkable. There are several bars/restaurants very close, and other areas are close enlighten to walk to as well (I.e. Congress Street). Commercial is a bit of a walk, but if you’re like us and love to walk a new area. It’s not that far. The bed is comfortable and the place was very clean. Communication was great. We would stay here again!"
The price is AU$257
includes taxes & fees
9 Sept - 10 Sept
Studio Unit Walkable Everywhere

Refurbished waterfront 1950s cabin with sauna, firepit, grill & kayaks - dogs ok

7.8 out of 10, Good, (14)
"We had a very nice stay cabin met all our needs"
Refurbished waterfront 1950s cabin with sauna, firepit, grill & kayaks - dogs ok

Full sized home

9.8 out of 10, Exceptional, (38)
"The house was lovely. Very comfortable place. Within 15- 20 mins to a store or restaurants."
The price is AU$565
includes taxes & fees
15 Sept - 16 Sept
Full sized home

In-town no frills 2 bedroom apt

8.0 out of 10, Very good, (8)
"It was perfect! The location was near everything downtown, which is what I was looking for."
The price is AU$258
includes taxes & fees
15 Sept - 16 Sept
In-town no frills 2 bedroom apt

Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough

2.0 star property
8.8 out of 10, Excellent, (10)
"Host was very receptive and responsive while on the property. We had a great time. "
Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough

Private Entrance Residential Portland

9.0 out of 10, Wonderful, (4)
"Great location for seeing the Portland Head Lighthouse. Comfortable bed."
The price is AU$257
includes taxes & fees
9 Sept - 10 Sept
Private Entrance Residential Portland

Sebago Lake Cottage on Raymond Cape

10.0 out of 10, Exceptional, (47)
"Very pleasant stay."
Sebago Lake Cottage on Raymond Cape

Serenity - Stunning Sebago Lake scenery

10.0 out of 10, Exceptional, (46)
"Nice house , nice host , everything was great!"
Serenity - Stunning Sebago Lake scenery

Waterfront Maine cottage! Next to Sebago Lake State Park!

9.4 out of 10, Exceptional, (28)
"We had a great stay! Thank you very much for a great vacation!"
Waterfront Maine cottage! Next to Sebago Lake State Park!

Spacious Historic Home | 7BR West End for Groups

10.0 out of 10, Exceptional, (5)
"Seven of us stayed at this beautiful home in a perfect location by the Western Promenade. Everyone had a comfortable bed, bathrooms and showers were plentiful, and the kitchen was perfectly appointed. Both cars we had fit into the garage (an added luxury). The beds were very comfortable and had soft sheets and fluffy towels. We loved every minute of our stay and made great use of the family room. Can't thank our hosts enough...very easy to work with and I would certainly rent from them again...
The price is AU$2,472
includes taxes & fees
10 Sept - 11 Sept
Spacious Historic Home | 7BR West End for Groups

Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

10.0 out of 10, Exceptional, (62)
"We had a great weekend celebrating our friend for her bachelorette! The house was perfect! Very clean, plenty of beds and bedrooms. It also is a quick uber ride away from old port. Meghan is a great host and i would highly recommended staying at this house. I would certainly go back! Thank you for having us!"
The price is AU$1,700
includes taxes & fees
9 Sept - 10 Sept
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

Elegant and efficient Island home 4 miles from downtown Portland

9.0 out of 10, Wonderful, (2)
"Historic and charming home in a most interesting setting-- the community was a former military fort and barracks. Chat with neighbors on the front porch or watch wildlife and hang out in the backyard picnic tables. Comfortable beds and two full baths makes it good for group of 4-6 people. The golf cart is a godsend but there are bicycles and kayaks for land and water exploration. We didn't make it to the lovely looking pool or rec center for gym/bowling but they look like lots of fun. Rental and...
Elegant and efficient Island home 4 miles from downtown Portland

Large, light filled 4 bedroom house - walk to ocean and ferry

10.0 out of 10, Exceptional, (34)
"I stayed here for a weekend with a group of friends and it was a dream! So lovely!"
Large, light filled 4 bedroom house - walk to ocean and ferry

Beautiful Oceanfront House- Stunning Water Views

9.6 out of 10, Exceptional, (15)
"The Host and his wife were so pleasant and accommodating. We enjoyed watching seals, fish and birds during our visit. Highly recommend."
Beautiful Oceanfront House- Stunning Water Views

Updated Long Island Maine Cottage

10.0 out of 10, Exceptional, (6)
"Great location. Comfortable living room. Well stocked kitchen. Great communication with owner."
Updated Long Island Maine Cottage
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

Top Cumberland Hotel Reviews

Find out more about Cumberland

Find out more about Cumberland

Everything you need to know about Cumberland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Cumberland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Cumberland holiday rentals: An excellent choice for every season

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

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Cumberland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cumberland holiday rentals we have selected for you start as low as AU$257 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Cumberland rentals

At Expedia, we put the best Cumberland holiday 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 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 holiday.

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. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Cumberland?

Yes, there are holiday rentals close to the most popular sights in Cumberland, 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 has to offer?

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach: This holiday home rental outside of Cumberland is located on the beach, and has a patio, a garden and a BBQ 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

What’s there to see and do in Cumberland?

Explore the area and family-friendly sights such as Portland Observatory, or get out into nature at a spot like Casco Bay. Desert of Maine and University of New England are a couple of places you'll find in the wider area.

What’s a holiday rental in Cumberland like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Cumberland. Holiday rentals offer amenities like laundry facilities and kitchens so you'll have everything you need. If you're concerned about a sanitised environment, a holiday rental can provide a sense of privacy away from public hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great choice for small groups.