Cumberland Holiday Rentals from AU$164: Search Short-Term Rentals

Q: 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.

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Our top choices for Cumberland holiday rentals

A compact living space with a sofa, a coffee table, a TV on a stand, a floor lamp, and a bookshelf.

1. Great suburban location close to town!

Deering Center

Kaley

includes taxes & fees

16 Nov - 17 Nov

A modern interior with a dining area, a living room, and a kitchen.

2. Studio Apartment in Freeport

Freeport

Susan S.

includes taxes & fees

2 Dec - 3 Dec

A narrow hallway with wooden flooring leading to a bedroom with a bed and a nightstand.

3. Portland 1-bedroom with enclosed porch & parking

Deering Center

Cricket C.

includes taxes & fees

16 Nov - 17 Nov

A cabin with two chairs facing a fire pit, surrounded by trees.

4. Cabin w/ bath + kitchenette | Hot tub add-on - 03

Freeport

Kirt v.

includes taxes & fees

15 Nov - 16 Nov

A compact kitchen with a dishwasher, microwave, and coffee maker on the countertop.

5. Quiet Spot in lovely Freeport neighborhood

Freeport

includes taxes & fees

15 Nov - 16 Nov

A staircase with wooden railings, two wooden chairs with cushions, a small table with a lamp, and a potted plant.

6. Fully Updated Airy Historic Home in South Freeport

Freeport

boodu

A bedroom with a wooden bed, a nightstand, a bench, a chair, and a ceiling with a light fixture.

7. Studio Apartment near downtown Walkable!

West Bayside

Rose

includes taxes & fees

19 Nov - 20 Nov

A modern kitchen with wooden cabinets, a black refrigerator, and a dining area with a wooden table and chairs.

8. Bright & Spacious Apartment with Amazing Shower

Parkside

Gintare V.

includes taxes & fees

17 Nov - 18 Nov

A modern kitchen with a central island, bar stools, a dining table, and a built-in oven.

9. The Weldon Hotel

Downtown Portland

Branden

includes taxes & fees

3 Dec - 4 Dec

A living room with a sofa, a coffee table, a TV, and a plant.

10. Beautiful 1st Floor Apartment & Amazing Shower

Parkside

Chloe C.

includes taxes & fees

18 Nov - 19 Nov

A cabin with a fire pit and outdoor seating.

11. Glamping cabin w/ full bath | Hot tub add-on - 21

Freeport

includes taxes & fees

15 Nov - 16 Nov

A kitchen with wooden cabinets, a stainless steel dishwasher, a coffee maker, and a potted plant.

12. Cozy Two Bedroom on Munjoy Hill

Munjoy Hill

includes taxes & fees

22 Nov - 23 Nov

A house surrounded by trees and a body of water.

13. Highland Lake House - Epic Lake Views, Easy Lake Access, Fully Appointed Home!

Windham

Michael S.

includes taxes & fees

20 Nov - 21 Nov

A kitchen with a wooden countertop, a black kettle, a vase with flowers, and a small wire basket.

14. Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland

Munjoy Hill

Ryan B.

includes taxes & fees

16 Nov - 17 Nov

A sandy beach with people and a play structure.

15. Sunny Spot with Private Parking

Knightville

Greg Z.

includes taxes & fees

15 Nov - 16 Nov

A multi-story building with a stone facade, large windows, and a flat roof with dormer windows.

16. Evalina Hotel

Downtown Portland

Eric

includes taxes & fees

13 Dec - 14 Dec

A spacious living room with a sofa, ottoman, and coffee table, a dining area with chairs, and a kitchen with cabinets and appliances.

17. Heated Game Room, Coastal Maine Cape Sleeps 10

Yarmouth

Michelle T.

A beach with people, a play structure, and a view of the sea.

18. Peaceful & minutes from Old Port w/private parking

Knightville

Kelly S.

includes taxes & fees

15 Nov - 16 Nov

A backyard with a white wooden fence, a small bush, a white wicker bench, and a stone wall in the background.

19. 1200 sq ft ♦ West End Townhouse ♦ Walk to Old Port

West End

Susan d.

includes taxes & fees

16 Nov - 17 Nov

A narrow pathway leading to a wooden house with a porch, surrounded by lush greenery and trees.

20. King Size Bed ♦ West End Studio ♦ Walk to Old Port

West End

Maureen R.

includes taxes & fees

17 Nov - 18 Nov

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Top Cumberland Hotel Reviews

Portland Harbor Hotel

10/10 Excellent

"Old hotel recently updated. Great location in Old Port in walking distance of restaurants and shop. Very helpful staff. Easy valet parking. They charge a resort fee but you get it back as credit to use for breakfast or at the bar. Great outdoor patio area with gas fire pit. Great vibe for adult travelers."

Inn at St John Portland In-Town

10/10 Excellent

"Each room is different, which is fun. I've stayed here many times and always happy with the place. A parking spot comes with the room in one of about 3 different lots very close to the hotel. There is an Asian market immediately next door where you can pick up some unique snacks and stuff too."

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$164 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 Portland Observatory, 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.

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Check prices for these dates

Our top choices for Cumberland holiday rentals

1. Great suburban location close to town!

2. Studio Apartment in Freeport

3. Portland 1-bedroom with enclosed porch & parking

4. Cabin w/ bath + kitchenette | Hot tub add-on - 03

5. Quiet Spot in lovely Freeport neighborhood

6. Fully Updated Airy Historic Home in South Freeport

7. Studio Apartment near downtown Walkable!

8. Bright & Spacious Apartment with Amazing Shower

9. The Weldon Hotel

10. Beautiful 1st Floor Apartment & Amazing Shower

11. Glamping cabin w/ full bath | Hot tub add-on - 21

12. Cozy Two Bedroom on Munjoy Hill

13. Highland Lake House - Epic Lake Views, Easy Lake Access, Fully Appointed Home!

14. Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland

15. Sunny Spot with Private Parking

16. Evalina Hotel

17. Heated Game Room, Coastal Maine Cape Sleeps 10

18. Peaceful & minutes from Old Port w/private parking

19. 1200 sq ft ♦ West End Townhouse ♦ Walk to Old Port

20. King Size Bed ♦ West End Studio ♦ Walk to Old Port

Find holiday rentals that suit your style

Top Cumberland Hotel Reviews

Portland Harbor Hotel

The Westin Portland Harborview

Holiday Inn Portland-By the Bay by IHG

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

Hampton Inn Portland Downtown - Waterfront

Inn at St John Portland In-Town

Portland Regency Hotel & Spa

Find out more about Cumberland

Frequently asked questions

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