Cumberland Holiday Rentals

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Holiday Rentals in Cumberland

The Weldon Hotel
4.5 star property
9.8 out of 10, Exceptional, (85)
"Loved this place and would definitely stay here next time we go back."
United States
Eleni
The price is AU$424
includes taxes & fees
9 Nov - 10 Nov
The Weldon Hotel
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
10.0 out of 10, Exceptional, (232)
"Tremendous stay, great property and host."
United States
Curtis G.
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, (5)
"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. "
United States
Tamerra J.
Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.
Sebago Lake Cottage on Raymond Cape
10.0 out of 10, Exceptional, (48)
"Our family was up for a wedding so we came up to visit. This is a beautiful place. We will keep this in mind for the future. "
United States
Stacy C.
Sebago Lake Cottage on Raymond Cape
In-town no frills 2 bedroom apt
8.4 out of 10, Very good, (14)
"Beds were very comfortable. Parking was a little difficult. 3rd floor was a little tough on my 83 year old mother. But it was clean and roomy and close to downtown shopping and touristy attractions."
United States
Betsy Jean
The price is AU$234
includes taxes & fees
1 Nov - 2 Nov
In-town no frills 2 bedroom apt
Refurbished waterfront 1950s cabin with sauna, firepit, grill & kayaks - dogs ok
7.8 out of 10, Good, (14)
"Loved the cabin and location"
United States
Michelle C.
Refurbished waterfront 1950s cabin with sauna, firepit, grill & kayaks - dogs ok
Studio Unit Walkable Everywhere
5.2 out of 10, (5)
"We didn't stay there at all. Canceled reservation "
United States
Dianne
The price is AU$210
includes taxes & fees
27 Oct - 28 Oct
Studio Unit Walkable Everywhere
1 room luxury ocean front studio cottage
9.6 out of 10, Exceptional, (163)
"Very clean beautiful view we definitely enjoyed ourselves "
United States
Ilona F.
1 room luxury ocean front studio cottage
Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough
2.0 star property
9.0 out of 10, Wonderful, (14)
"Very responsive host, even got us a pack and play for our youngest! Perfect house for a beach stay! Would stay again! "
United States
Matthew D.
Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough
Private Lakefront Estate with 180 Degree Views
10.0 out of 10, Exceptional, (7)
"This was a fabulous property in perfect location. The house and grounds were amazing. It was a sensational week."
United States
Brian C.
Private Lakefront Estate with 180 Degree Views
Serenity - Stunning Sebago Lake scenery
10.0 out of 10, Exceptional, (50)
"We had an amazing stay at this property and will book again! Owner is responsive and helped us with a few questions we had during our stay. Beds were comfortable and the house was clean. Great vacation filled with great memories! "
United States
Anonymous traveller
Serenity - Stunning Sebago Lake scenery
Best house in Old Orchard Beach..STEPS/BEACH, surf!!!! 4 bedroom
9.8 out of 10, Exceptional, (44)
"Great house with lots of room for a big family. So close to the beach with great views. Great outdoor spaces as well! "
United States
Moria B.
Best house in Old Orchard Beach..STEPS/BEACH, surf!!!! 4 bedroom
Updated Long Island Maine Cottage
10.0 out of 10, Exceptional, (7)
"Great location. Comfortable living room. Well stocked kitchen. Great communication with owner."
United States
patricia s.
Updated Long Island Maine Cottage
Private Entrance Residential Portland
9.2 out of 10, Wonderful, (5)
"Great location for seeing the Portland Head Lighthouse. Comfortable bed."
United States
Michelle S.
The price is AU$226
includes taxes & fees
27 Oct - 28 Oct
Private Entrance Residential Portland
Great Place for a Family Retreat! Sleeps 10
9.6 out of 10, Exceptional, (13)
"Nice clean property close to everything."
United States
Dean P.
Great Place for a Family Retreat! Sleeps 10
Gem on Congress - King Bed, Free Parking, Dog & Family Friendly, Modern Condo
10.0 out of 10, Exceptional, (18)
"We loved the walkable neighborhood & had a great, comfortable stay!"
United States
Erin R.
The price is AU$775
includes taxes & fees
27 Oct - 28 Oct
Gem on Congress - King Bed, Free Parking, Dog & Family Friendly, Modern Condo
Back yard paradise
9.8 out of 10, Exceptional, (22)
"Excellent home overall! Great equipment, great kitchen, great pool, nice patio! Easy access to the home and driveway! Probably the best house I’ve stayed in ! "
United States
Justin J.
Back yard paradise
Ultimate Pine Point Beach Family Compound-4 Units, 8 Bedrooms, Yard
10.0 out of 10, Exceptional, (6)
"This property was a great place for our extended family to stay, as the different cottages could house different parts of the family. The houses were clean, and the location was great! It was close to the beaches, restaurants, and salt marsh. We would definitely stay here again!"
United States
Vicki W.
The price is AU$4,447
includes taxes & fees
9 Nov - 10 Nov
Ultimate Pine Point Beach Family Compound-4 Units, 8 Bedrooms, Yard
Charming 2-bedroom house with AC, WiFi in lovely Falmouth
8.8 out of 10, Excellent, (6)
"We had a wonderful stay. Nice comfortable camp. We enjoyed swimming in the lake. "
United States
Darcie B.
Charming 2-bedroom house with AC, WiFi in lovely Falmouth
Knock on Wood | Airy Charm in Heart of Downtown
8.8 out of 10, Excellent, (24)
"This apartment is so well situated to walk to parks, restaurants and shopping. It’s a very large space and quite comfortable. "
United States
beth H.
The price is AU$590
includes taxes & fees
6 Nov - 7 Nov
Knock on Wood | Airy Charm in Heart of Downtown
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 Hotel Reviews

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$210 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.