Cumberland Vacation Rentals from AED 592: Search Short-Term Rentals

Q: What's the top vacation rental that Cumberland has to offer?

Charming 110-year former Inn 10' from the Ocean! : This vacation home rental near Cumberland is located on the beach and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

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Our top choices for Cumberland vacation 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

Deering Center

Ameleah B.

AED 408 total

includes taxes & fees

27 Oct - 28 Oct

A cabin with a fire pit and outdoor seating.

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

Freeport

AED 1,834 total

includes taxes & fees

27 Oct - 28 Oct

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

3. Great suburban location close to town!

Deering Center

AED 356 total

includes taxes & fees

27 Oct - 28 Oct

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

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

Freeport

Michael H.

AED 1,277 total

includes taxes & fees

4 Oct - 5 Oct

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

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

Yarmouth

Gina H.

AED 3,670 total

includes taxes & fees

29 Sep - 30 Sep

A dining area with a wooden table, two chairs, and a window with a view of trees.

6. Cozy 1 BR ADU | Private Access | Projector Theater

Windham

Traci P.

AED 1,738 total

includes taxes & fees

27 Oct - 28 Oct

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

Munjoy Hill

Emily N.

AED 905 total

includes taxes & fees

20 Oct - 21 Oct

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

8. Adorable Portland getaway on the Eastern Promenade

Munjoy Hill

Kiernan

AED 1,009 total

includes taxes & fees

26 Oct - 27 Oct

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

9. Beautiful 1st Floor Apartment & Amazing Shower

Parkside

Jocelyn R.

AED 604 total

includes taxes & fees

29 Sep - 30 Sep

A two-story house with a covered porch, a garage, and a front yard with potted plants.

10. Large suite/private bath/private entrance on quiet street near Thomas Bay

Brunswick

DENESE

AED 597 total

includes taxes & fees

29 Sep - 30 Sep

A modern kitchen with white cabinets, a wooden dining table, and a vase with green leaves.

11. King Size Sun Rise Midcoast Lovely Stay

Topsham

Tabcline S.

AED 909 total

includes taxes & fees

29 Sep - 30 Sep

A dining table with chairs, a potted plant, and decorative items.

12. Willard Beach–Apartment Near Portland & Parks

Willard Beach

Robert B.

AED 1,178 total

includes taxes & fees

27 Oct - 28 Oct

A spacious living room with large windows, a sofa, a chair, and a small table.

13. 1 Mi to Maine Street! Mcm-style Home in Brunswick

Brunswick

AED 996 total

includes taxes & fees

20 Oct - 21 Oct

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

14. Studio Apartment near downtown Walkable!

West Bayside

Krysta

AED 592 total

includes taxes & fees

6 Oct - 7 Oct

A modern kitchen with a wooden countertop, a glass coffee table, and a built-in shelf with kitchenware.

15. Sunny Spot with Private Parking.

Knightville

Irish D.

AED 1,129 total

includes taxes & fees

27 Oct - 28 Oct

A hallway leading to a living room with a sofa, a lamp, and a window.

16. The Coastal Connection

Thorton Heights

Sheryl S.

AED 1,234 total

includes taxes & fees

29 Sep - 30 Sep

A wooden deck with outdoor seating and string lights.

17. Full sized home

Harpswell

Angela M.

AED 1,275 total

includes taxes & fees

5 Oct - 6 Oct

A modern house with a wooden exterior, a small garden, and a visible window.

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

East Bayside

Mallory D.

AED 1,619 total

includes taxes & fees

4 Oct - 5 Oct

A lakeside property with a deck, picnic table, and barbecue grill.

19. Camp Forever cottage

Harpswell

Dennis H.

AED 1,261 total

includes taxes & fees

3 Oct - 4 Oct

A window with a view of a snowy landscape and bare trees.

20. Tranquility between the Lakes & Sea

Westbrook

AED 1,142 total

includes taxes & fees

1 Oct - 2 Oct

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Top Cumberland Hotel Reviews

Hampton Inn Portland Downtown - Waterfront

10/10 Excellent

"The water pressure wasn’t the best and the pillows were pretty soft but other than that, it was a nice stay"

Portland Regency Hotel & Spa

8/10 Good

"The hotel was nice, the staff was friendly, the valet was completely necessary!! The rooms are clean and comfortable, but a little dated in the decor. The morning coffee and tea was a nice touch. Our room didn't have much of a view, but the bathroom was a good size with plenty of towels for our stay and the bed was comfortable. We didn't have any issues when we requested an extra blanket and the valet was always available and didn't take long to get our car. Great location to be able to walk to everything in downtown. Easy check-in check-out experience no issues. Would recommend if you want easy in/out parking with a valet and a very walkable hotel in downtown portland. Biggest pet peeve: tv only has cable option; can't login to streaming services like Netflix/Hulu."

Inn at St John Portland In-Town

8/10 Good

"Room was adequate for one overnight. I understood the room size requirements, but the furniture made the space feel cramped. I was also aware there was no elevator, but that being said, theres not really a space between floors for you to stop and catch your breath on. Also it had a mild musty smell. Breakfast was bare bones but was included so thats fine. Quick 10 minutes from the airport which was nice."

Clarion Pointe South Portland

10/10 Excellent

"For our purpose the location was perfect. The room was large and nicely done. Comfortable beds. Breakfast was the usual fair, adequate. pool was very nice. The best part was that it has a GREAT casual restaurant connected to the hotel, Coopersmith. We have already booked for the end of Oct. Thank you for a great stay. Heather and Jim"

Frequently asked questions

Are there vacation rentals in Cumberland?

Yes, there are vacation rentals in Cumberland close to Greely Center for the Arts, or you can choose a more secluded option if you want a relaxing stay.

What's the top vacation rental that Cumberland has to offer?

Charming 110-year former Inn 10' from the Ocean!: This vacation home rental near Cumberland is located on the beach and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation 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 larger area.

What’s a vacation rental in Cumberland like?

Vacation rentals are private properties you can book for several days or longer in Cumberland. Vacation rentals offer extras such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a clean environment, vacation rentals can offer a sense of safety away from public hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for family gatherings.

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Check prices for these dates

Our top choices for Cumberland vacation rentals

1. Portland 1-bedroom with enclosed porch & parking

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

3. Great suburban location close to town!

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

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

6. Cozy 1 BR ADU | Private Access | Projector Theater

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

8. Adorable Portland getaway on the Eastern Promenade

9. Beautiful 1st Floor Apartment & Amazing Shower

10. Large suite/private bath/private entrance on quiet street near Thomas Bay

11. King Size Sun Rise Midcoast Lovely Stay

12. Willard Beach–Apartment Near Portland & Parks

13. 1 Mi to Maine Street! Mcm-style Home in Brunswick

14. Studio Apartment near downtown Walkable!

15. Sunny Spot with Private Parking.

16. The Coastal Connection

17. Full sized home

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

19. Camp Forever cottage

20. Tranquility between the Lakes & Sea

Find vacation rentals that suit your style

Top Cumberland Hotel Reviews

Hampton Inn Portland Downtown - Waterfront

Portland Regency Hotel & Spa

Portland Harbor Hotel

Embassy Suites by Hilton Portland Maine

Inn at St John Portland In-Town

Clarion Pointe South Portland

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

Cambria Hotel Portland Downtown-Old Port

Spark by Hilton Portland Airport Maine Mall

Frequently asked questions

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