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Cumberland Vacation Rentals

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Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Cumberland vacation rentals

TV

Private Entrance Residential Portland

Private Entrance Residential Portland
Deering Center
8.4 out of 10, Very Good, (7 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 ￥17,900
￥21,439 total
includes taxes & fees
Aug 2 - Aug 3
Private Entrance Residential Portland
Property grounds

Modern cabin w/ full bath & kitchenette - 03

Modern cabin w/ full bath & kitchenette - 03
Freeport
10.0 out of 10, Exceptional, (7 reviews)
"This was a perfect little cabin. It was clean, well equipped with a nice kitchen and bathroom, quiet and wooded location, and comfy bed. "
United States
Chris B.
The price is ￥39,453
￥63,887 total
includes taxes & fees
Jul 26 - Jul 27
Modern cabin w/ full bath & kitchenette - 03
Honeymoon Studio | Egyptian cotton sheets, premium bedding, down comforters, bed sheets

Fortland Island Campground

Fortland Island Campground
1.0 star property
Portland
10.0 out of 10, Exceptional, (3 reviews)
"It was very quiet and liked the experience of staying in a camp like setting."
United States
leela srinivas
The price is ￥35,529
￥38,726 total
includes taxes & fees
Jul 21 - Jul 22
Fortland Island Campground
Property grounds

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 ￥39,453
￥63,533 total
includes taxes & fees
Jul 27 - Jul 28
Glamping cabin w/ full bath + spa access - 21
1 bedroom, WiFi, bed sheets

Studio Apartment near downtown Walkable!

Studio Apartment near downtown Walkable!
West Bayside
8.2 out of 10, Very Good, (10 reviews)
"Check in process was smooth and description of area was accurate though cleanliness of unit left a lot to be desired. There was a lot of hair all over the apartment floor and bedding when we arrived with old stains in bedding. Booked 2 nights and ended up getting a hotel for the 2nd day."
United States
Raul
The price is ￥18,753
￥30,941 total
includes taxes & fees
Jul 22 - Jul 23
Studio Apartment near downtown Walkable!
Property grounds

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, (38 reviews)
"Overall a pleasing stay."
United States
Mallory D.
The price is ￥22,674
￥74,064 total
includes taxes & fees
Jul 19 - Jul 20
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
Dining

Elegant condo - walk to Portland's best restaurants & Old Port

Elegant condo - walk to Portland's best restaurants & Old Port
East Bayside
9.4 out of 10, Exceptional, (81 reviews)
"Lovely unit. Very comfortable bed. Nice to have off street parking. Walkable to Old Port. Would def stay again. "
United States
Erin H.
The price is ￥27,236
￥81,053 total
includes taxes & fees
Jul 29 - Jul 30
Elegant condo - walk to Portland's best restaurants & Old Port
Terrace/patio

Sebago Lake studio-style condo with enclosed sunroom and sunset views

Sebago Lake studio-style condo with enclosed sunroom and sunset views
Standish
8.6 out of 10, Excellent, (4 reviews)
"Awesome quaint unit with water views, close to everything. Awesome community and communication!"
United States
James B.
The price is ￥29,182
￥42,411 total
includes taxes & fees
Jul 29 - Jul 30
Sebago Lake studio-style condo with enclosed sunroom and sunset views
Beach

City Amenities, Casco Bay Sunrises and Natural Beauty

City Amenities, Casco Bay Sunrises and Natural Beauty
East Deering
9.8 out of 10, Exceptional, (130 reviews)
"Wonderful place! Owner very responsible! Would stay again! Great choice for place to stay away from home."
United States
Arlene L.
City Amenities, Casco Bay Sunrises and Natural Beauty
Dining

Modern Apartment - 20 Mins to Portland, Deck, Grill & Firepit, King Bed, DogsOK

Modern Apartment - 20 Mins to Portland, Deck, Grill & Firepit, King Bed, DogsOK
Westbrook
10.0 out of 10, Exceptional, (11 reviews)
"Fantastic property. Hosts were very communicative. Amazing stay. Great location! Thank you so much!"
United States
Laurie A.
The price is ￥35,459
￥83,248 total
includes taxes & fees
Jul 20 - Jul 21
Modern Apartment - 20 Mins to Portland, Deck, Grill & Firepit, King Bed, DogsOK
Outdoor dining

Sebago Lake Cottage on Raymond Cape

Sebago Lake Cottage on Raymond Cape
Raymond
10.0 out of 10, Exceptional, (49 reviews)
"This little cabin was so clean and comfortable!! Very well equipped kitchenette. Comfortable bed too. Everything we needed and more!"
United States
Teresa G.
The price is ￥28,731
￥50,854 total
includes taxes & fees
Aug 7 - Aug 8
Sebago Lake Cottage on Raymond Cape
Outdoor dining

'Osprey Cottage' South Freeport Home on Casco Bay!

'Osprey Cottage' South Freeport Home on Casco Bay!
Freeport
8.8 out of 10, Excellent, (22 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.
The price is ￥53,416
￥104,944 total
includes taxes & fees
Jul 19 - Jul 20
'Osprey Cottage' South Freeport Home on Casco Bay!
Interior

Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
9.8 out of 10, Exceptional, (29 reviews)
"Cute property.. also really suitable for long stay as the amenities were complete and near groceries and some restaurants and cafes.. convenient!"
United States
Giana
The price is ￥39,616
￥62,471 total
includes taxes & fees
Jul 20 - Jul 21
Sunny Spot with Private Parking.
Property grounds

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 ￥65,513
￥93,498 total
includes taxes & fees
Jul 18 - Jul 19
WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
Exterior

Luxury on Back Cove - Three Gables

Luxury on Back Cove - Three Gables
Rosemont
10.0 out of 10, Exceptional, (9 reviews)
"GoodLocation, very clean. Would stay again "
United States
Carly B.
The price is ￥40,155
￥94,914 total
includes taxes & fees
Jul 19 - Jul 20
Luxury on Back Cove - Three Gables
Interior

1200 sq ft ♦ West End Townhouse ♦ Perfect Location

1200 sq ft ♦ West End Townhouse ♦ Perfect Location
West End
8.4 out of 10, Very Good, (61 reviews)
"Nice place. Good location."
United States
Rob M.
The price is ￥23,832
￥69,271 total
includes taxes & fees
Aug 11 - Aug 12
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
Cottage (2 Bedrooms) | Interior

'osprey Cottage' South Freeport Home on Casco Bay!

'osprey Cottage' South Freeport Home on Casco Bay!
3.0 star property
Freeport
The price is ￥64,132
￥99,697 total
includes taxes & fees
Jul 19 - Jul 20
'osprey Cottage' South Freeport Home on Casco Bay!
Smart TV, fireplace

Cozy 2-bedroom house with shared beach access to Sebago Lake

Cozy 2-bedroom house with shared beach access to Sebago Lake
Raymond
The price is ￥36,531
￥45,305 total
includes taxes & fees
Jul 21 - Jul 22
Cozy 2-bedroom house with shared beach access to Sebago Lake
3 bedrooms, premium bedding, iron/ironing board, travel crib

Cozy 3BR | Pet Friendly | Near Portland | Parking

Cozy 3BR | Pet Friendly | Near Portland | Parking
Westbrook
10.0 out of 10, Exceptional, (13 reviews)
"We had a great stay here. It was very clean and conveniently located."
United States
Angela B.
The price is ￥42,863
￥88,663 total
includes taxes & fees
Aug 9 - Aug 10
Cozy 3BR | Pet Friendly | Near Portland | Parking
Outdoor dining

Peaceful & minutes from the Old Port with private parking

Peaceful & minutes from the Old Port with private parking
Knightville
9.6 out of 10, Exceptional, (10 reviews)
"Apartment was very cute, clean, and just what I was looking for. Jennifer was very accommodating and understanding "
United States
Jolee S.
The price is ￥45,136
￥70,966 total
includes taxes & fees
Jul 21 - Jul 22
Peaceful & minutes from the Old Port with private parking
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

Comfort Inn South Portland Airport

Comfort Inn South Portland Airport

10/10 Excellent
"Great location!"
Valerie 1-night trip
Posted 1 hour ago
Comfort Inn South Portland Airport

Find out more about Cumberland

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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?

Cozy & Quiet Home in Portland Maine. One Bedroom, Private Bathroom “No Kitchen”: This vacation home rental near Cumberland is located on the beach and offers a fireplace, air-conditioning, and free WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave, and an electric kettle.

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.