Holiday Rentals Cumberland from £114: Find Short-Term Rentals & Holiday Accommodations

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

1. Luxe 5 Bed/ 3 Bath with Game Room & AC

Yarmouth

Michelle T.

includes taxes & fees

13 Oct - 14 Oct

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

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

Freeport

Michael H.

includes taxes & fees

8 Oct - 9 Oct

A geodesic dome structure in a forest setting with a visible interior space.

3. Modern dome w/ full bath + spa access - 04

Freeport

Rene B.

includes taxes & fees

20 Oct - 21 Oct

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

4. The Weldon Hotel

Downtown Portland

Victoria

includes taxes & fees

2 Nov - 3 Nov

A multi-story building with a stone facade, large windows, and a corner entrance.

5. Evalina Hotel

Downtown Portland

Rick

includes taxes & fees

3 Nov - 4 Nov

A dirt path in a park with autumn foliage.

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

Westbrook

Genevieve W.

includes taxes & fees

12 Oct - 13 Oct

A cabin with a fire pit and outdoor seating.

7. Modern glamping cabin w/ full bath + kitchen - 19

Freeport

Kathleen K.

includes taxes & fees

13 Oct - 14 Oct

8. Luna 22-ft dome w/ star loft & full bath - 07

Freeport

Andrew L.

includes taxes & fees

8 Oct - 9 Oct

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

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

Munjoy Hill

Emily N.

includes taxes & fees

1 Nov - 2 Nov

A street lined with buildings, one with a red door and a sign that reads "MINATO".

10. Glorious getaway on Portland's Eastern Promenade.

Munjoy Hill

William

includes taxes & fees

14 Oct - 15 Oct

11. Adorable Portland getaway on the Eastern Promenade

Munjoy Hill

Kiernan

includes taxes & fees

21 Oct - 22 Oct

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

Freeport

includes taxes & fees

18 Oct - 19 Oct

A spacious living area with a blue sofa, a coffee table, and a kitchen in the background.

13. New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10

North Deering

Peter H.

includes taxes & fees

18 Oct - 19 Oct

A hallway with a large, rustic mirror leaning against the wall, a potted plant in the foreground, and a glimpse of a bed with a yellow blanket in the background.

14. Lush Coastal Downtown Home - Beaches & Shopping

Freeport

Alana K.

includes taxes & fees

8 Oct - 9 Oct

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

15. Portland 1-bedroom with enclosed porch & parking

Deering Center

Lance

includes taxes & fees

14 Oct - 15 Oct

A bedroom with a bed, a nightstand, a lamp, a door, and a staircase.

16. Great suburban location close to town!

Deering Center

Peter H.

includes taxes & fees

25 Oct - 26 Oct

17. Ocean View East End Studio in a Historic Victorian

Portland

Ryan S.

includes taxes & fees

14 Oct - 15 Oct

A room with a wooden floor, a round table, two chairs, a sofa, and a patterned rug.

18. NEW 1 BDR-Heart of Munjoy Hill

Munjoy Hill

Susan

includes taxes & fees

8 Oct - 9 Oct

A wooden house with a deck and a stone pathway leading to a grassy area.

19. Waterfront Couples Retreat w/Porch, Private Patio, Freeport, Near LL Bean

Freeport

Hana L.

includes taxes & fees

25 Oct - 26 Oct

A gray house with a black front door, white trim, and a number 70 sign.

20. Vintage Maine & Modern Convenience in Portlands Exclusive East End

Munjoy Hill

maureen

includes taxes & fees

15 Oct - 16 Oct

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Top Cumberland Hotel Reviews

Tru by Hilton Portland Airport Area

8/10 Good

"Staff members absolutely amazing even prior to checking in. There was a problem with the system generating keys, The staff made sure we could get in our room and rest. Hats off to the weekend staff!"

Inn at St John Portland In-Town

8/10 Good

"The inn itself was beautifully kept. The water pressure was great. There was plenty of hot water except very early in the morning (before 6am). I didn’t walk in the area but if I had too, I wouldn’t feel comfortable in the evening. There was parking behind the hotel and I was lucky to get a spot both nights that I was there otherwise you would have to park in their other lot somewhere around the corner. They had lemon water, fruit, cookies, tea and coffee out all the time. The included breakfast was just an easy grab a toasted bagel and go. Nothing special but it was a nice offer. The beds were soft, the AC worked well and our room was very large. Our room was on the second floor, no elevator and extremely steep steps, but staff was always available to help with bags or luggage. Overall, a very nice stay and less expensive than closer to town."

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

10/10 Excellent

"The room clean and the property was well kept. The included breakfast was solid for a hotel breakfast. My only complaints would be that we didnt have hand soap which took a few tries to track down because the desk staff was away when we came back late night, the other complaint is the elevator door is scary loud but it functions properly, just something wonky with the door"

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 £114 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 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. Luxe 5 Bed/ 3 Bath with Game Room & AC

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

3. Modern dome w/ full bath + spa access - 04

4. The Weldon Hotel

5. Evalina Hotel

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

7. Modern glamping cabin w/ full bath + kitchen - 19

8. Luna 22-ft dome w/ star loft & full bath - 07

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

10. Glorious getaway on Portland's Eastern Promenade.

11. Adorable Portland getaway on the Eastern Promenade

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

13. New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10

14. Lush Coastal Downtown Home - Beaches & Shopping

15. Portland 1-bedroom with enclosed porch & parking

16. Great suburban location close to town!

17. Ocean View East End Studio in a Historic Victorian

18. NEW 1 BDR-Heart of Munjoy Hill

19. Waterfront Couples Retreat w/Porch, Private Patio, Freeport, Near LL Bean

20. Vintage Maine & Modern Convenience in Portlands Exclusive East End

Find holiday rentals that suit your style

Top Cumberland Hotel Reviews

Tru by Hilton Portland Airport Area

Inn at St John Portland In-Town

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

Clarion Hotel Portland Airport ME

Portland Regency Hotel & Spa

The Westin Portland Harborview

Fireside Inn & Suites Portland

DoubleTree by Hilton Hotel Portland

Quality Inn & Suites South Portland

Find out more about Cumberland

Frequently asked questions

Go further with the Expedia app

Search Holiday Rentals in Cumberland

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Cumberland holiday rentals

1. Luxe 5 Bed/ 3 Bath with Game Room & AC

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

3. Modern dome w/ full bath + spa access - 04

4. The Weldon Hotel

5. Evalina Hotel

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

7. Modern glamping cabin w/ full bath + kitchen - 19

8. Luna 22-ft dome w/ star loft & full bath - 07

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

10. Glorious getaway on Portland's Eastern Promenade.

11. Adorable Portland getaway on the Eastern Promenade

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

13. New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10

14. Lush Coastal Downtown Home - Beaches & Shopping

15. Portland 1-bedroom with enclosed porch & parking

16. Great suburban location close to town!

17. Ocean View East End Studio in a Historic Victorian

18. NEW 1 BDR-Heart of Munjoy Hill

19. Waterfront Couples Retreat w/Porch, Private Patio, Freeport, Near LL Bean

20. Vintage Maine & Modern Convenience in Portlands Exclusive East End

Find holiday rentals that suit your style

Top Cumberland Hotel Reviews

Tru by Hilton Portland Airport Area

Find out more about Cumberland

Frequently asked questions

Go further with the Expedia app