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Cumberland Holiday Rentals

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Check prices for these dates

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

Our top choices for Cumberland holiday rentals

A living room with a sofa, armchair, and glass coffee table. There are two lamps on side tables and a window with curtains.

1. Portland 1-bedroom with enclosed porch & parking

Portland 1-bedroom with enclosed porch & parking
Deering Center
8.0 out of 10, Very good, (13 reviews)
"This was a great place to stay. Easy to get to all of our destinations. Place was clean and comfortable. Would stay here again. "
United States
Ameleah B.
The price is AU$153
includes taxes & fees
28 Sept - 29 Sept
Portland 1-bedroom with enclosed porch & parking
A cabin with two chairs facing a fire pit, surrounded by trees.

2. Modern cabin w/ full bath & kitchenette - 03

Modern cabin w/ full bath & kitchenette - 03
Freeport
10.0 out of 10, Exceptional, (8 reviews)
"Easy check in process. More than clean, it looked brand new. Overall a great stay. Kitchen was well stocked with plates, utensils, and cookware. "
United States
Michael H.
The price is AU$438
includes taxes & fees
30 Sept - 1 Oct
Modern cabin w/ full bath & kitchenette - 03
A kitchen with wooden cabinets, a refrigerator, a sink, and a window with blinds.

3. Great suburban location close to town!

Great suburban location close to town!
Deering Center
The price is AU$155
includes taxes & fees
27 Sept - 28 Sept
Great suburban location close to town!
A wooden bench on a rocky shore overlooking a calm body of water.

4. City Amenities, Casco Bay Sunrises and Natural Beauty

City Amenities, Casco Bay Sunrises and Natural Beauty
East Deering
9.8 out of 10, Exceptional, (133 reviews)
"Wonderful place! Owner very responsible! Would stay again! Great choice for place to stay away from home."
United States
Arlene L.
City Amenities, Casco Bay Sunrises and Natural Beauty
A cabin with a fire pit and outdoor seating.

5. Glamping cabin w/ full bath + spa access - 21

Glamping cabin w/ full bath + spa access - 21
Freeport
10.0 out of 10, Exceptional, (1 review)
The price is AU$555
includes taxes & fees
7 Oct - 8 Oct
Glamping cabin w/ full bath + spa access - 21
A spacious living room with large windows, a sofa, a chair, and a small table.

6. 1 Mi to Maine Street! MCM-Style Home in Brunswick

1 Mi to Maine Street! MCM-Style Home in Brunswick
Brunswick
9.6 out of 10, Exceptional, (12 reviews)
"Quiet, clean, well appointed house close to Maine St Brunswick and convenient to both Portland and points north. "
United States
Kendra G.
1 Mi to Maine Street! MCM-Style Home in Brunswick
A kitchen with a wooden countertop, a black kettle, a vase with flowers, and a small wire basket.

7. Charming Studio apartment with WiFi, AC in welcoming Portland

Charming Studio apartment with WiFi, AC in welcoming Portland
Munjoy Hill
9.6 out of 10, Exceptional, (28 reviews)
"Great place! We would definitely return if we were in the area."
United States
Preston
The price is AU$332
includes taxes & fees
20 Oct - 21 Oct
Charming Studio apartment with WiFi, AC in welcoming Portland
A dirt path in a park with autumn foliage.

8. WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres

WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
Westbrook
9.6 out of 10, Exceptional, (43 reviews)
"Host was excellent, even thinking of bug spray, yoga mats, binoculars, and extra blankets. We loved our stay!"
United States
Genevieve W.
The price is AU$873
includes taxes & fees
2 Oct - 3 Oct
WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
A bedroom with a wooden bed, a nightstand, a bench, a chair, and a ceiling with a light fixture.

9. Studio Apartment near downtown Walkable!

Studio Apartment near downtown Walkable!
West Bayside
8.4 out of 10, Very good, (19 reviews)
"I will admit the location and surrounding areas are a bit sketchy, but, once inside, we felt super secure. There are multiple doors and gates with locks to ensure safety. Place was clean and had everything we needed for a quick stay."
United States
Krysta
The price is AU$232
includes taxes & fees
6 Oct - 7 Oct
Studio Apartment near downtown Walkable!
A spacious kitchen with a large island, wooden beams, and a view of the outdoors.

10. Waterfront Access with Kayaks, Private Deck and a Firepit

Waterfront Access with Kayaks, Private Deck and a Firepit
Gray
9.8 out of 10, Exceptional, (7 reviews)
"In frosty conditions the house was warm and comfortable. Jen was really responsive and welcoming, and the space was perfect."
United States
Matthew S.
The price is AU$1,052
includes taxes & fees
12 Oct - 13 Oct
Waterfront Access with Kayaks, Private Deck and a Firepit
A dining area with a white table and chairs, a bowl of fruit, a framed artwork, and a potted plant.

11. Peaceful & minutes from the Old Port with private parking

Peaceful & minutes from the Old Port with private parking
Knightville
9.8 out of 10, Exceptional, (13 reviews)
"Cute, convenient spot!"
United States
Kelly S.
The price is AU$554
includes taxes & fees
27 Sept - 28 Sept
Peaceful & minutes from the Old Port with private parking
A street lined with buildings, one with a red door and a sign that reads "MINATO".

12. Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (147 reviews)
"Owner was so accommodating!"
United States
Kiernan
The price is AU$407
includes taxes & fees
20 Oct - 21 Oct
Adorable Portland getaway on the Eastern Promenade
A beach with a wooden chair and a small building in the background.

13. Arlie`s Digs! - One Block To Willard Beach!

Arlie`s Digs! - One Block To Willard Beach!
Willard Beach
10.0 out of 10, Exceptional, (70 reviews)
"Beautiful place, perfect location! "
United States
Melissa M.
The price is AU$757
includes taxes & fees
25 Oct - 26 Oct
Arlie`s Digs! - One Block To Willard Beach!
A modern house with a wooden exterior, a small garden, and a visible window.

14. Spacious and Contemporary Condo in the Heart of Portland - Close to Beach

Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
East Bayside
8.8 out of 10, Excellent, (40 reviews)
"Overall a pleasing stay."
United States
Mallory D.
The price is AU$655
includes taxes & fees
4 Oct - 5 Oct
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
A modern kitchen with a wooden countertop, a glass coffee table, and a built-in shelf with kitchenware.

15. Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
10.0 out of 10, Exceptional, (33 reviews)
"This is a perfect location. 6 minutes from downtown Portland. Secure, Clean and Jen was a Perfect and attentive host. It is a hidden Gem!"
United States
Irish D.
The price is AU$460
includes taxes & fees
29 Sept - 30 Sept
Sunny Spot with Private Parking.
A bedroom with a large bed, white curtains, and a view through the windows.

16. Cozy 3BR | Pet Friendly | Near Portland | Parking

Cozy 3BR | Pet Friendly | Near Portland | Parking
Westbrook
10.0 out of 10, Exceptional, (14 reviews)
"We had a great stay here. It was very clean and conveniently located."
United States
Angela B.
The price is AU$686
includes taxes & fees
5 Oct - 6 Oct
Cozy 3BR | Pet Friendly | Near Portland | Parking
A spacious living room with large windows, a sofa, a chair, and a small table.

17. 1 Mi to Maine Street! Mcm-style Home in Brunswick

1 Mi to Maine Street! Mcm-style Home in Brunswick
3.0 star property
Brunswick
The price is AU$385
includes taxes & fees
20 Oct - 21 Oct
1 Mi to Maine Street! Mcm-style Home in Brunswick
A modern interior with a glass door leading to an outdoor deck with a sofa and a dining table.

18. Cozy Stay w/ Roof Deck | Parking | 5 Min Downtown

Cozy Stay w/ Roof Deck | Parking | 5 Min Downtown
Oakdale
10.0 out of 10, Exceptional, (6 reviews)
"Excellent stay! 3rd floor unit so walk up the stairs is needed. The space was beautifully decorated, and the hosts even had flowers waiting upon arrival. Very cozy with the fireplace and huge outdoor patio. Would love to stay again!"
United States
Ilyna W.
Cozy Stay w/ Roof Deck | Parking | 5 Min Downtown
A dining table with chairs, a potted plant, and decorative items.

19. Willard Beach–Apartment Near Portland & Parks

Willard Beach–Apartment Near Portland & Parks
Willard Beach
10.0 out of 10, Exceptional, (7 reviews)
"Excellent in every way."
United States
Robert B.
The price is AU$560
includes taxes & fees
25 Oct - 26 Oct
Willard Beach–Apartment Near Portland & Parks
A gym with treadmills, elliptical machines, and exercise balls.

20. 1-bedroom hotel suites in Scarborough with essentially stocked kitchens.

1-bedroom hotel suites in Scarborough with essentially stocked kitchens.
South Portland
9.2 out of 10, Wonderful, (19 reviews)
"We really appreciated our stay!"
United States
Anonymous traveller
The price is AU$254
includes taxes & fees
30 Sept - 1 Oct
1-bedroom hotel suites in Scarborough with essentially stocked kitchens.
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

Spark by Hilton Portland Airport Maine Mall

Spark by Hilton Portland Airport Maine Mall

8/10 Good
"The gentleman who managed the breakfast room was terrific. The fan in the bathroom was irritatingly loud."
Lynn 1-night trip
Posted less than an hour ago
Spark by Hilton Portland Airport Maine Mall

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$232 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 in Cumberland close to Greely Center for the Arts, 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?

Charming 110-year former Inn 10' from the Ocean!: This holiday home rental outside of Cumberland is located on the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. You can relax into your holiday with a garden and 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, or get out into nature at a spot like Casco Bay. Greely Center for the Arts and Desert of Maine 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.