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Cumberland Holiday Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 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, (14 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 HK$659
HK$830 total
includes taxes & fees
30 Sept - 1 Oct
Portland 1-bedroom with enclosed porch & parking
A cabin with a fire pit and outdoor seating.

2. 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 HK$1,765
HK$2,727 total
includes taxes & fees
4 Oct - 5 Oct
Glamping cabin w/ full bath + spa access - 21
A bedroom with a bed, a nightstand, a lamp, a door, and a staircase.

3. Great suburban location close to town!

Great suburban location close to town!
Deering Center
10.0 out of 10, Exceptional, (1 review)
"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 HK$588
HK$759 total
includes taxes & fees
25 Oct - 26 Oct
Great suburban location close to town!
A cabin with two chairs facing a fire pit, surrounded by trees.

4. 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 HK$1,765
HK$2,727 total
includes taxes & fees
4 Oct - 5 Oct
Modern cabin w/ full bath & kitchenette - 03
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

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 HK$3,212
HK$7,460 total
includes taxes & fees
30 Sept - 1 Oct
Luxe 5 Bed/ 3 Bath with Game Room & AC
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

Cozy 1 BR ADU | Private Access | Projector Theater
Windham
10.0 out of 10, Exceptional, (5 reviews)
"Very clean! Small space (no microwave) pet friendly and very accommodating to our travel needs!"
United States
Traci P.
The price is HK$926
HK$3,651 total
includes taxes & fees
27 Oct - 28 Oct
Cozy 1 BR ADU | Private Access | Projector Theater
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, (29 reviews)
"Loved this spot and would stay again. Had everything you needed and a great location. Cute little attic spot but nice and cool."
United States
Emily N.
The price is HK$1,161
HK$1,949 total
includes taxes & fees
20 Oct - 21 Oct
Charming Studio apartment with WiFi, AC in welcoming Portland
A street lined with buildings, one with a red door and a sign that reads "MINATO".

8. Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (149 reviews)
"Owner was so accommodating!"
United States
Kiernan
The price is HK$1,388
HK$2,155 total
includes taxes & fees
20 Oct - 21 Oct
Adorable Portland getaway on the Eastern Promenade
A living room with a sofa, armchairs, a coffee table, and a potted plant.

9. Beautiful 1st Floor Apartment & Amazing Shower

Beautiful 1st Floor Apartment & Amazing Shower
Parkside
9.0 out of 10, Wonderful, (32 reviews)
"This was a clean and good location for our stay. "
United States
Jocelyn R.
The price is HK$1,070
HK$1,808 total
includes taxes & fees
6 Oct - 7 Oct
Beautiful 1st Floor Apartment & Amazing Shower
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

Large suite/private bath/private entrance on quiet street near Thomas Bay
Brunswick
10.0 out of 10, Exceptional, (172 reviews)
"What a beautiful place to stay. Jeff and Susan made your stay a very special experience."
United States
DENESE
The price is HK$1,012
HK$1,274 total
includes taxes & fees
30 Sept - 1 Oct
Large suite/private bath/private entrance on quiet street near Thomas Bay
A modern kitchen with white cabinets, a wooden dining table, and a vase with green leaves.

11. King Size Sun Rise Midcoast Lovely Stay

King Size Sun Rise Midcoast Lovely Stay
Topsham
9.6 out of 10, Exceptional, (18 reviews)
"Perfect for a my husband and I. Close to everything!"
United States
Tabcline S.
The price is HK$981
HK$1,941 total
includes taxes & fees
30 Sept - 1 Oct
King Size Sun Rise Midcoast Lovely Stay
A dining table with chairs, a potted plant, and decorative items.

12. Willard Beach–Apartment Near Portland & Parks

Willard Beach–Apartment Near Portland & Parks
Willard Beach
10.0 out of 10, Exceptional, (8 reviews)
"Excellent in every way."
United States
Robert B.
The price is HK$1,346
HK$2,656 total
includes taxes & fees
26 Oct - 27 Oct
Willard Beach–Apartment Near Portland & Parks
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

1 Mi to Maine Street! Mcm-style Home in Brunswick
3.0 star property
Brunswick
The price is HK$800
HK$2,127 total
includes taxes & fees
20 Oct - 21 Oct
1 Mi to Maine Street! Mcm-style Home in Brunswick
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!

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 HK$700
HK$1,263 total
includes taxes & fees
25 Oct - 26 Oct
Studio Apartment near downtown Walkable!
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, (34 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 HK$1,545
HK$2,411 total
includes taxes & fees
5 Oct - 6 Oct
Sunny Spot with Private Parking.
A hallway leading to a living room with a sofa, a lamp, and a window.

16. The Coastal Connection

The Coastal Connection
Thorton Heights
7.2 out of 10, Good, (7 reviews)
"Very convenient, comfortable, and bright apartment. We appreciated that dogs were allowed as well."
United States
Sheryl S.
The price is HK$1,059
HK$2,608 total
includes taxes & fees
30 Sept - 1 Oct
The Coastal Connection
A wooden deck with outdoor seating and string lights.

17. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (71 reviews)
"The house was lovely and well kept and in a great location."
United States
Angela M.
The price is HK$1,588
HK$2,723 total
includes taxes & fees
5 Oct - 6 Oct
Full sized home
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

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 HK$1,095
HK$3,458 total
includes taxes & fees
4 Oct - 5 Oct
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
A lakeside property with a deck, picnic table, and barbecue grill.

19. Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (68 reviews)
"Everything was great, fantastic location!"
United States
Dennis H.
The price is HK$1,647
HK$2,693 total
includes taxes & fees
3 Oct - 4 Oct
Camp Forever cottage
A window with a view of a snowy landscape and bare trees.

20. Tranquility between the Lakes & Sea

Tranquility between the Lakes & Sea
Westbrook
The price is HK$904
HK$2,439 total
includes taxes & fees
4 Oct - 5 Oct
Tranquility between the Lakes & Sea
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

Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG

10/10 Excellent
"It was convenient"
Matthew 2-night trip
Posted 4 hours ago
Holiday Inn Portland-By the Bay by IHG

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 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.