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Cumberland Vacation Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Cumberland vacation rentals

Cottage (2 Bedrooms) | Interior

1. 'osprey Cottage' South Freeport Home on Casco Bay!

'osprey Cottage' South Freeport Home on Casco Bay!
3.0 star property
Freeport
'osprey Cottage' South Freeport Home on Casco Bay!
Property grounds

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

Modern dome w/ full bath + spa access - 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 SAR 632
SAR 1,168 total
includes taxes & fees
23 Sep - 24 Sep
Modern dome w/ full bath + spa access - 04
Outdoor dining

3. 'Osprey Cottage' South Freeport Home on Casco Bay!

'Osprey Cottage' South Freeport Home on Casco Bay!
Freeport
8.8 out of 10, Excellent, (23 reviews)
"This was an adorable cottage in a picturesque location. The cottage was clean and comfortable, right on the water. Additional friends stayed in the adjacent Heron cottage, and we joined them on the patio for a fire one evening as summer faded to autumn."
United States
John J.
'Osprey Cottage' South Freeport Home on Casco Bay!
Property grounds

4. 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 SAR 1,653
SAR 2,363 total
includes taxes & fees
22 Sep - 23 Sep
WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
Beach

5. City Amenities, Casco Bay Sunrises and Natural Beauty

City Amenities, Casco Bay Sunrises and Natural Beauty
East Deering
9.8 out of 10, Exceptional, (132 reviews)
"Wonderful place! Owner very responsible! Would stay again! Great choice for place to stay away from home."
United States
Arlene L.
The price is SAR 896
SAR 1,562 total
includes taxes & fees
22 Sep - 23 Sep
City Amenities, Casco Bay Sunrises and Natural Beauty
Property grounds

6. 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 SAR 845
SAR 1,388 total
includes taxes & fees
30 Sep - 1 Oct
Modern cabin w/ full bath & kitchenette - 03
Interior

7. Lush Coastal Downtown Home - Beaches & Shopping

Lush Coastal Downtown Home - Beaches & Shopping
Freeport
10.0 out of 10, Exceptional, (6 reviews)
"Our stay was very comfortable and easy to navigate. The host was very communicative. We had everything we needed and more. It was nice to be in walking distance from downtown Freeport. Although the price was higher than we wanted, our family of four (2 teens) enjoyed having a clean, comfortable and seamless stay."
United States
Alana K.
The price is SAR 1,285
SAR 2,289 total
includes taxes & fees
5 Oct - 6 Oct
Lush Coastal Downtown Home - Beaches & Shopping
Property grounds

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

Waterfront Couples Retreat w/Porch, Private Patio, Freeport, Near LL Bean
Freeport
10.0 out of 10, Exceptional, (17 reviews)
"Hosts were very responsive with messages. The stay was clean and comfortable."
United States
Hana L.
Waterfront Couples Retreat w/Porch, Private Patio, Freeport, Near LL Bean
Exterior detail

9. 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, (81 reviews)
"Everything was very well stocked!"
United States
Sally O.
The price is SAR 2,705
SAR 4,279 total
includes taxes & fees
22 Sep - 23 Sep
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port
Exterior detail

10. Glorious getaway on Portland's Eastern Promenade.

Glorious getaway on Portland's Eastern Promenade.
Munjoy Hill
9.8 out of 10, Exceptional, (184 reviews)
"Wonderful experience with exceptional hosts!"
United States
Cynthia
The price is SAR 1,116
SAR 1,740 total
includes taxes & fees
28 Sep - 29 Sep
Glorious getaway on Portland's Eastern Promenade.
Exterior

11. 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, (171 reviews)
"What a beautiful place to stay. Jeff and Susan made your stay a very special experience."
United States
DENESE
The price is SAR 485
SAR 610 total
includes taxes & fees
22 Sep - 23 Sep
Large suite/private bath/private entrance on quiet street near Thomas Bay
Deluxe Suite, 1 King Bed | Private kitchen | Coffee/tea maker, full-size fridge, microwave, oven

12. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (119 reviews)
"Really nice room and location"
United States
Victoria
The price is SAR 1,501
SAR 1,918 total
includes taxes & fees
18 Oct - 19 Oct
The Weldon Hotel
Interior

13. Three bedroom in United States of America, Freeport

Three bedroom in United States of America, Freeport
Freeport
9.8 out of 10, Exceptional, (10 reviews)
The price is SAR 1,587
SAR 3,613 total
includes taxes & fees
12 Oct - 13 Oct
Three bedroom in United States of America, Freeport
Exterior

14. Ocean View East End Studio in a Historic Victorian

Ocean View East End Studio in a Historic Victorian
Portland
10.0 out of 10, Exceptional, (112 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 SAR 1,127
SAR 1,732 total
includes taxes & fees
27 Sep - 28 Sep
Ocean View East End Studio in a Historic Victorian
Exterior detail

15. Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (147 reviews)
"Owner was so accommodating!"
United States
Kiernan
The price is SAR 665
SAR 1,081 total
includes taxes & fees
20 Oct - 21 Oct
Adorable Portland getaway on the Eastern Promenade
Property grounds

16. Centerview cottage

Centerview cottage
Harpswell
9.6 out of 10, Exceptional, (72 reviews)
"Incredible home in a beautiful location!"
United States
Catherine G.
The price is SAR 1,108
SAR 1,711 total
includes taxes & fees
22 Sep - 23 Sep
Centerview cottage
Beach

17. THE RALEIGH BnB APARTMENT SELF CHECK-IN / Free Off-Street Parking

THE RALEIGH BnB APARTMENT SELF CHECK-IN / Free Off-Street Parking
Munjoy Hill
10.0 out of 10, Exceptional, (4 reviews)
"Great place, so close to everything and a clean, quiet spot to sleep."
United States
Dan K.
THE RALEIGH BnB APARTMENT SELF CHECK-IN / Free Off-Street Parking
Front of property

18. Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (11 reviews)
"Truly a wonderful place with an unbeatable location. Highly recommend for a visit to Portland."
United States
Eric
The price is SAR 2,172
SAR 2,931 total
includes taxes & fees
19 Oct - 20 Oct
Evalina Hotel
Terrace/patio

19. Full sized home

Full sized home
Harpswell
9.8 out of 10, Exceptional, (69 reviews)
"The house was lovely and well kept and in a great location."
United States
Angela M.
The price is SAR 761
SAR 1,386 total
includes taxes & fees
22 Sep - 23 Sep
Full sized home
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

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

10/10 Excellent
"We had a great stay. The room was clean and comfortable."
Destalia 1-night trip
Posted less than an hour ago
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

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.