Cumberland Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Cumberland vacation rentals

Exterior
Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach

Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach

Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach
Brunswick
10.0 out of 10, Exceptional, (145)
"Lovely space, comfortable bed, very convenient to downtown Brunswick."
United States
Kimberly G.
The price is ￥14,051
￥18,719 total
includes taxes & fees
Dec 28 - Dec 29
Large suite/private bath/private entrance on quiet street near Thomas Pt. Beach
Interior
Brunswick Downtown Sugar Cube next to Bowdoin

Brunswick Downtown Sugar Cube next to Bowdoin

Brunswick Downtown Sugar Cube next to Bowdoin
Brunswick
8.4 out of 10, Very Good, (7)
"Stayed for one night. Very convenient to campus"
United States
Lin-Lin R.
The price is ￥14,831
￥41,181 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Brunswick Downtown Sugar Cube next to Bowdoin
Private kitchen
Classic New England 1st Floor 3 BR Downtown Brunswick

Classic New England 1st Floor 3 BR Downtown Brunswick

Classic New England 1st Floor 3 BR Downtown Brunswick
Brunswick
9.6 out of 10, Exceptional, (9)
"We had a good time in Brunswick.... great location and jumping off point to explore."
United States
Karin S.
The price is ￥35,303
￥72,342 total
includes taxes & fees
Dec 28 - Dec 29
Classic New England 1st Floor 3 BR Downtown Brunswick
Smart TV, books
Little Lincoln beautiful home

Little Lincoln beautiful home

Little Lincoln beautiful home
Brunswick
9.2 out of 10, Wonderful, (15)
"Simon was very easy to communicate with, the place was clean, the bed was quite comfortable, and we were right by Main Street in Brunswick which made for easy access to food and things to do. Wonderful place to stay!"
United States
Jessica B.
The price is ￥19,515
￥46,797 total
includes taxes & fees
Dec 28 - Dec 29
Little Lincoln beautiful home
Fridge, microwave, oven, stovetop
Pine Point Beach private, quaint, charming studio.

Pine Point Beach private, quaint, charming studio.

Pine Point Beach private, quaint, charming studio.
2.0 star property
Blue Point
10.0 out of 10, Exceptional, (24)
"Cozy, clean and comfortable! Perfect weekend beach get away! "
United States
jen e.
The price is ￥12,490
￥31,142 total
includes taxes & fees
Dec 28 - Dec 29
Pine Point Beach private, quaint, charming studio.
Dining
Sunny Spot with Private Parking.

Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
2.0 star property
Knightville
9.8 out of 10, Exceptional, (24)
"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 ￥15,144
￥31,312 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Sunny Spot with Private Parking.
Fridge, microwave, oven, stovetop
Beautiful 3BR Home with Office in Town of Brunswick with King beds

Beautiful 3BR Home with Office in Town of Brunswick with King beds

Beautiful 3BR Home with Office in Town of Brunswick with King beds
Brunswick
9.2 out of 10, Wonderful, (5)
"Great place for our family to stay while visiting the Maine coast."
United States
Craig C.
The price is ￥23,535
￥57,976 total
includes taxes & fees
Dec 27 - Dec 28
Beautiful 3BR Home with Office in Town of Brunswick with King beds
Interior
Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (127)
"Very convenient location. Comfortable accommodation! I would stay here again. "
United States
Cynthia W.
The price is ￥11,603
￥25,475 total
includes taxes & fees
Dec 25 - Dec 26
Adorable Portland getaway on the Eastern Promenade
Exterior
Large, luxurious geodesic dome - 02

Large, luxurious geodesic dome - 02

Large, luxurious geodesic dome - 02
Freeport
10.0 out of 10, Exceptional, (1)
"Doug our host always was ready to answer any questions we had and we loved his sense of humor "
United States
Alice A.
The price is ￥34,815
￥56,837 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Large, luxurious geodesic dome - 02
Outdoor dining
Peaceful & minutes from the Old Port with private parking

Peaceful & minutes from the Old Port with private parking

Peaceful & minutes from the Old Port with private parking
Knightville
9.8 out of 10, Exceptional, (7)
"This well- appointed apartment was perfect for our stay in the Portland area. Jennifer was always quick to answer any questions. We would definitely recommend this listing."
United States
Lynn E.
The price is ￥15,300
￥33,524 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Peaceful & minutes from the Old Port with private parking
Fridge, microwave, oven, stovetop
Private Home w/ Office Year Round in town Brunswick next to Bowdoin

Private Home w/ Office Year Round in town Brunswick next to Bowdoin

Private Home w/ Office Year Round in town Brunswick next to Bowdoin
Brunswick
9.0 out of 10, Wonderful, (24)
"Nice place, I'd stay again!"
United States
Ronnie C.
The price is ￥23,418
￥61,091 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Private Home w/ Office Year Round in town Brunswick next to Bowdoin
TV
In-town no frills 2 bedroom apt

In-town no frills 2 bedroom apt

In-town no frills 2 bedroom apt
West Bayside
8.6 out of 10, Excellent, (16)
"Good place to stay in. Safe. However, it would be good to know about the steep and narrow spiral staircase, in case you have lots of heavy luggage."
United States
Omar S.
The price is ￥11,532
￥22,797 total
includes taxes & fees
Dec 25 - Dec 26
In-town no frills 2 bedroom apt
Fridge, microwave, oven, stovetop
2King Bed BR Private Apt Downtown Brunswick

2King Bed BR Private Apt Downtown Brunswick

2King Bed BR Private Apt Downtown Brunswick
Brunswick
8.4 out of 10, Very Good, (10)
"Small place in a great location. Easily walk to several shops and restaurants. "
United States
Jillian B.
The price is ￥15,612
￥37,438 total
includes taxes & fees
Jan 4 - Jan 5, 2026
2King Bed BR Private Apt Downtown Brunswick
Interior
City Amenities, Casco Bay Sunrises and Natural Beauty

City Amenities, Casco Bay Sunrises and Natural Beauty

City Amenities, Casco Bay Sunrises and Natural Beauty
East Deering
9.8 out of 10, Exceptional, (122)
"The house was clean and homey…everything was well stocked and supplies were even there for our pet…great access to the highway…the views were beautiful…would definitely recommend! "
United States
Michelle M.
The price is ￥22,481
￥46,797 total
includes taxes & fees
Dec 28 - Dec 29
City Amenities, Casco Bay Sunrises and Natural Beauty
Beach
Sunset Hideaway on Bailey Island

Sunset Hideaway on Bailey Island

Sunset Hideaway on Bailey Island
Harpswell
8.0 out of 10, Very Good, (4)
"We really enjoyed our stay on Bailey Island. The apartment was clean and comfortable. The kitchen was well stocked and former renters had even left some food in the fridge.The house is in a sweet little, quiet community. Would recommend. Thanks"
United States
Reen and Gordon H.
The price is ￥16,847
￥36,103 total
includes taxes & fees
Dec 28 - Dec 29
Sunset Hideaway on Bailey Island
Outdoor dining
Vacation Creation Downtown Brunswick 2King Beds

Vacation Creation Downtown Brunswick 2King Beds

Vacation Creation Downtown Brunswick 2King Beds
Brunswick
9.6 out of 10, Exceptional, (18)
"Stayed here while visiting Bowdoin. Great place!"
United States
Deborah B.
Vacation Creation Downtown Brunswick 2King Beds
1 bedroom, WiFi, bed sheets
Studio Apartment near downtown Walkable!

Studio Apartment near downtown Walkable!

Studio Apartment near downtown Walkable!
West Bayside
8.4 out of 10, Very Good, (7)
"The summary and the pictures shown are exactly what you’re going to get. The owner did a good job with the description, I "
United States
Alexandria T.
The price is ￥9,885
￥21,150 total
includes taxes & fees
Dec 29 - Dec 30
Studio Apartment near downtown Walkable!
Outdoor dining
Camp Forever cottage

Camp Forever cottage

Camp Forever cottage
Harpswell
9.6 out of 10, Exceptional, (58)
"Perfect location on the water for a weekend getaway"
United States
Lydia G.
The price is ￥29,507
￥52,583 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Camp Forever cottage
Smart TV, books
Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)

Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)

Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)
Brunswick
9.8 out of 10, Exceptional, (28)
"This property is newly renovated and is in a great location--right across from the Brunswick Hotel and next to campus. Parking is easy (in the driveway) and the apartment is really spacious!"
United States
Jill C.
The price is ￥21,076
￥54,284 total
includes taxes & fees
Dec 28 - Dec 29
Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound)
Fridge, microwave, oven, stovetop
Maine Luxury Home On the Sea

Maine Luxury Home On the Sea

Maine Luxury Home On the Sea
Brunswick
The price is ￥33,577
￥109,092 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Maine Luxury Home On the 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Cumberland Hotel Reviews

Tru by Hilton Portland Airport Area

Tru by Hilton Portland Airport Area

10/10 Excellent
"Yes"
Norman 1-night trip
Posted 1 day ago
Tru by Hilton Portland Airport Area

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:

  • View our selection of featured holiday rentals in Cumberland
  • Use the map to find apartments and other holiday homes in the Cumberland neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Cumberland while they last

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 close to well known attractions in Cumberland, or you can select a more remote option if you'd like a relaxing place to stay.

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

Back yard paradise: This vacation home near Cumberland is located on a lake and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a patio and a garden.

What’s there to see and do in Cumberland?

Explore the area and family-friendly sights such as Maine Narrow Gauge Railroad Company and Museum, or get out into nature at a spot like Casco Bay. Desert of Maine and University of New England 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.