Holiday Rentals in Cumberland

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Our top choices for Cumberland holiday rentals

8.4 out of 10, Very good, (7)
"Stayed for one night. Very convenient to campus"
United States
Lin-Lin R.
Brunswick Downtown Sugar Cube next to Bowdoin
10.0 out of 10, Exceptional, (145)
"Great location to access the area especially route 1 n and s. Room totally met our needs and Susan and Jeff were super nice. This place will make our trip most memorable!"
United States
Don E.
The price is €106
includes taxes & fees
18 Jan - 19 Jan 2026
Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach
2.0 star property
10.0 out of 10, Exceptional, (25)
"Cozy, clean and comfortable! Perfect weekend beach get away! "
United States
jen e.
The price is €182
includes taxes & fees
4 Jan - 5 Jan 2026
Pine Point Beach private, quaint, charming studio.

Apartment in Brunswick

Little Lincoln beautiful home
9.2 out of 10, Wonderful, (15)
"Simon was very easy to communicate with, the place was clean, the bed was quite comfortable, and we were right by Main Street in Brunswick which made for easy access to food and things to do. Wonderful place to stay!"
United States
Jessica B.
The price is €224
includes taxes & fees
25 Jan - 26 Jan 2026
Little Lincoln beautiful home
8.4 out of 10, Very good, (10)
"Small place in a great location. Easily walk to several shops and restaurants. "
United States
Jillian B.
The price is €212
includes taxes & fees
28 Jan - 29 Jan 2026
2King Bed BR Private Apt Downtown Brunswick

Apartment in Freeport

Studio Apartment in Freeport
2.0 star property
Studio Apartment in Freeport
10.0 out of 10, Exceptional, (3)
"Awesome camping in a great, quiet campground. The staff is very responsive and all the little details make this place special."
United States
Miranda K.
The price is €258
includes taxes & fees
4 Jan - 5 Jan 2026
Modern, Luxurious, Cabin in the Woods - 17

Apartment in Knightville

Sunny Spot with Private Parking.
2.0 star property
9.8 out of 10, Exceptional, (25)
"Cute property.. also really suitable for long stay as the amenities were complete and near groceries and some restaurants and cafes.. convenient!"
United States
Giana
The price is €174
includes taxes & fees
25 Jan - 26 Jan 2026
Sunny Spot with Private Parking.
10.0 out of 10, Exceptional, (2)
"Super location, very private, responsive host, lovely, clean. Very lucky to have been able to stay here!"
United States
Kate K.
Bird Watching Paradise @ Waterfront Harpswell with Private Deck
9.8 out of 10, Exceptional, (28)
"This property is newly renovated and is in a great location--right across from the Brunswick Hotel and next to campus. Parking is easy (in the driveway) and the apartment is really spacious!"
United States
Jill C.
Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)
9.8 out of 10, Exceptional, (52)
"Great location and cozy."
United States
Heather G.
The price is €200
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy, Elegant and Bright 2 bed in the East End
9.8 out of 10, Exceptional, (7)
"This well- appointed apartment was perfect for our stay in the Portland area. Jennifer was always quick to answer any questions. We would definitely recommend this listing."
United States
Lynn E.
The price is €185
includes taxes & fees
4 Jan - 5 Jan 2026
Peaceful & minutes from the Old Port with private parking
8.4 out of 10, Very good, (7)
"The summary and the pictures shown are exactly what you’re going to get. The owner did a good job with the description, I "
United States
Alexandria T.
The price is €118
includes taxes & fees
9 Jan - 10 Jan 2026
Studio Apartment near downtown Walkable!

Apartment in West Bayside

In-town no frills 2 bedroom apt
8.6 out of 10, Excellent, (17)
"Good place to stay in. Safe. However, it would be good to know about the steep and narrow spiral staircase, in case you have lots of heavy luggage."
United States
Omar S.
The price is €136
includes taxes & fees
1 Jan - 2 Jan 2026
In-town no frills 2 bedroom apt

Holiday Home in Brunswick

Maine Luxury Home On the Sea
The price is €559
includes taxes & fees
7 Jan - 8 Jan 2026
Maine Luxury Home On the Sea
2.0 star property
10.0 out of 10, Exceptional, (4)
"Host was very welcoming and check in was simple "
United States
Michael C.
The price is €113
includes taxes & fees
1 Jan - 2 Jan 2026
Spacious Studio Near Sebago Lake
9.6 out of 10, Exceptional, (11)
"A great location and a comfortable place to stay!"
United States
Andrew K.
The price is €184
includes taxes & fees
1 Jan - 2 Jan 2026
Charming Studio apartment with WiFi, AC in welcoming Portland
9.0 out of 10, Wonderful, (26)
"This was a clean and good location for our stay. "
United States
Jocelyn R.
The price is €149
includes taxes & fees
26 Jan - 27 Jan 2026
Beautiful 1st Floor Apartment & Amazing Shower

Holiday Home in Harpswell

Orchid Harbor, Bailey Island 3BR
9.8 out of 10, Exceptional, (9)
"Orchid Harbor was perfect for my 3 week escape from life. Bailey Island is quiet and the house is comfortable and accommodating for family and friends.The outdoor seating along the ocean was our favorite place to be."
United States
Karen T.
The price is €434
includes taxes & fees
1 Jan - 2 Jan 2026
Orchid Harbor, Bailey Island 3BR

Holiday Home in Harpswell

Full sized home
9.8 out of 10, Exceptional, (50)
"It was a very nice house to stay at. "
United States
Anonymous traveller
The price is €316
includes taxes & fees
26 Jan - 27 Jan 2026
Full sized home
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, apart-hotels, 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 favorite 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 depends 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 €118 per night. Entering your travel dates in the search wizard you might find 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 Maine Narrow Gauge Railroad Company and Museum, 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.