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Cumberland Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Cumberland vacation 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

Luxe 5 Bed/ 3 Bath with Game Room & AC
Yarmouth
10.0 out of 10, Exceptional, (4 reviews)
"What a great place to stay! The home is very clean and very quiet. Our host was very responsive to any questions we had. We would book this one over and over again."
United States
Michelle T.
The price is ￥81,775
￥170,778 total
includes taxes & fees
Oct 18 - Oct 19
Luxe 5 Bed/ 3 Bath with Game Room & AC
A cabin with two chairs facing a fire pit, surrounded by trees.

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

Cabin w/ bath + kitchenette | Hot tub add-on - 03
Freeport
9.8 out of 10, Exceptional, (10 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 ￥28,017
￥48,452 total
includes taxes & fees
Oct 18 - Oct 19
Cabin w/ bath + kitchenette | Hot tub add-on - 03
A dirt path in a park with autumn foliage.

3. 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 ￥69,545
￥98,712 total
includes taxes & fees
Oct 18 - Oct 19
WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
A geodesic dome structure in a forest setting with a visible interior space.

4. Modern dome w/ full bath | Hot tub add-on - 04

Modern dome w/ full bath | Hot tub add-on - 04
Freeport
10.0 out of 10, Exceptional, (5 reviews)
"Pet friendly and the experience is just amazing. Thank you for having us! "
United States
Rene B.
The price is ￥41,812
￥67,966 total
includes taxes & fees
Oct 21 - Oct 22
Modern dome w/ full bath | Hot tub add-on - 04
A house with a wooden front door, a stone staircase, and a porch with a wooden railing.

5. Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
East Deering
10.0 out of 10, Exceptional, (82 reviews)
"Absolutely perfect rental!Great location with an amazing view!"
United States
Mike G.
The price is ￥110,219
￥175,601 total
includes taxes & fees
Oct 18 - Oct 19
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
A spacious living area with a blue sofa, a coffee table, and a kitchen in the background.

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

New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10
North Deering
9.4 out of 10, Exceptional, (16 reviews)
"The house was perfect for our week in Portland. New, great features in the home, lovely backyard and close to everything Portland"
United States
Patrick J.
The price is ￥65,420
￥127,092 total
includes taxes & fees
Oct 18 - Oct 19
New Luxury Maine Home Hot Tub, Fire Pit, Sleeps 10
A living room with a sofa, armchair, and glass coffee table. There are two lamps on side tables and a window with curtains.

7. Portland 1-bedroom with enclosed porch & parking

Portland 1-bedroom with enclosed porch & parking
Deering Center
8.2 out of 10, Very good, (16 reviews)
"Easy to get to, and a great night's sleep.Want to stay in Portland but in a quiet neighborhood?-Grab this spot!"
United States
Cricket C.
The price is ￥14,103
￥17,548 total
includes taxes & fees
Oct 27 - Oct 28
Portland 1-bedroom with enclosed porch & parking
A modern kitchen with a central island, bar stools, a dining table, and a built-in oven.

8. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (126 reviews)
"Really nice room and location"
United States
Victoria
The price is ￥30,900
￥45,533 total
includes taxes & fees
Nov 8 - Nov 9
The Weldon Hotel
A modern interior with a dining area, a living room, and a kitchen.

9. Studio Apartment in Freeport

Studio Apartment in Freeport
Freeport
10.0 out of 10, Exceptional, (4 reviews)
"The bed was the most comfortable I have ever slept on! Lovely large warm open room. I appreciated the coffee/tea options, and the condiments in the fridge. There was a white noise machine in the room though we did not use it."
United States
Susan S.
The price is ￥11,061
￥24,983 total
includes taxes & fees
Nov 2 - Nov 3
Studio Apartment in Freeport
A multi-story building with a stone facade, large windows, and a corner entrance.

10. Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (15 reviews)
"This is a very nice hotel in a great location. It’s new and wonderfully appointed. Everything about it is first class."
United States
Rick
The price is ￥42,080
￥69,571 total
includes taxes & fees
Nov 16 - Nov 17
Evalina Hotel
A modern kitchen with dark cabinetry, stainless steel appliances, and a large island.

11. Gorgeous 3-bedroom house in charming Portland

Gorgeous 3-bedroom house in charming Portland
North Deering
9.0 out of 10, Wonderful, (4 reviews)
"This place was exactly as it looks in the photos. Really conveniently located with good amenities."
United States
Bridget M.
The price is ￥58,625
￥107,478 total
includes taxes & fees
Oct 31 - Nov 1
Gorgeous 3-bedroom house in charming Portland
A street lined with buildings, one with a red door and a sign that reads "MINATO".

12. Glorious getaway on Portland's Eastern Promenade.

Glorious getaway on Portland's Eastern Promenade.
Munjoy Hill
9.8 out of 10, Exceptional, (189 reviews)
"The property is well equipped for a long weekend. Parking was convenient. The location offered a quiet place to stay just minutes from Portland’s bustling commercial corridors. Will definitely look to book again on our next visit."
United States
William
The price is ￥37,206
￥61,912 total
includes taxes & fees
Oct 18 - Oct 19
Glorious getaway on Portland's Eastern Promenade.
A bedroom with a bed, a nightstand, a lamp, a door, and a staircase.

13. Great suburban location close to town!

Great suburban location close to town!
Deering Center
10.0 out of 10, Exceptional, (2 reviews)
"Small but cozy space, well kept, good value for the price and has all the amenities you could expect. Would be happy to stay here again."
United States
Peter H.
The price is ￥11,852
￥15,297 total
includes taxes & fees
Oct 25 - Oct 26
Great suburban location close to town!
A cabin with a fire pit and outdoor seating.

14. Modern cabin w/ full bath | Hot tub add-on - 19

Modern cabin w/ full bath | Hot tub add-on - 19
Freeport
10.0 out of 10, Exceptional, (5 reviews)
"Great location to Freeport shopping. Very clean and responsive staff and management. Fun for families with children. We would have liked more room inbetween cabins, but otherwise would highly recommend."
United States
Kathleen K.
The price is ￥29,724
￥51,174 total
includes taxes & fees
Oct 19 - Oct 20
Modern cabin w/ full bath | Hot tub add-on - 19
Exterior

15. Ocean View East End Studio in a Historic Victorian

Ocean View East End Studio in a Historic Victorian
Portland
9.8 out of 10, Exceptional, (114 reviews)
"Fantastic host, fantastic place, fantastic location. 30 second walk out to a massive green lawned park overlooking the water. Easy stroll downtown. Dan was a very friendly, welcoming, and accommodating host. We had a great stay and would return again."
United States
Ryan S.
The price is ￥47,406
￥73,375 total
includes taxes & fees
Oct 18 - Oct 19
Ocean View East End Studio in a Historic Victorian
A kitchen with a wooden countertop, a black kettle, a vase with flowers, and a small wire basket.

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

Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland
Munjoy Hill
9.4 out of 10, Exceptional, (32 reviews)
"Had a wonderful stay. Very clean and great location."
United States
Aimee S.
The price is ￥19,753
￥36,344 total
includes taxes & fees
Nov 1 - Nov 2
Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland
A street lined with buildings, one with a red door and a sign that reads "MINATO".

17. Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (155 reviews)
"Owner was so accommodating!"
United States
Kiernan
The price is ￥27,970
￥45,645 total
includes taxes & fees
Oct 26 - Oct 27
Adorable Portland getaway on the Eastern Promenade
A cabin with a fire pit and outdoor seating.

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

Glamping cabin w/ full bath | Hot tub add-on - 21
Freeport
10.0 out of 10, Exceptional, (1 review)
The price is ￥28,017
￥48,969 total
includes taxes & fees
Oct 18 - Oct 19
Glamping cabin w/ full bath | Hot tub add-on - 21
A garden with a stone bridge over a small stream, surrounded by various plants and flowers.

19. Peaceful Oasis on Munjoy Hill 2nd flr 3BR parking

Peaceful Oasis on Munjoy Hill 2nd flr 3BR parking
Munjoy Hill
9.8 out of 10, Exceptional, (7 reviews)
"10/10 would stay again Close to nice bars,restaurants, gas stations. Clean apartment. Host was very nice! "
United States
Mary C.
The price is ￥34,820
￥65,684 total
includes taxes & fees
Nov 4 - Nov 5
Peaceful Oasis on Munjoy Hill 2nd flr 3BR parking
A geodesic dome structure in a forest setting with a visible interior space.

20. 22-ft dome w/ star loft | Hot tub add-on - 07

22-ft dome w/ star loft | Hot tub add-on - 07
Freeport
10.0 out of 10, Exceptional, (1 review)
"Fun place with all amenities. Had an excellent time!"
United States
Andrew L.
The price is ￥44,799
￥71,740 total
includes taxes & fees
Oct 27 - Oct 28
22-ft dome w/ star loft | Hot tub add-on - 07
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
"Close to airport. Good for 1 night stay"
Nivedtha 1-night trip
Posted less than an hour ago
Spark by Hilton Portland Airport Maine Mall

Find out more about Cumberland

Search for holiday rentals in Cumberland on Expedia! You can easily find your home rentals, villas, holiday apartments in Cumberland using one of the methods below:

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Look no further and take a look at our great range of rental properties in Cumberland!

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 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 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.