A coastal lighthouse with red-roofed houses, rocky shoreline, and the ocean.

Vacation Rentals in Cumberland County

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Top Cities in Cumberland County

A lighthouse, a white house with a red roof, and rocky coastline at sunset.
Vacation RentalsVacation Rentals

Portland

Portland

Our top choices for Cumberland County vacation rentals

A two-story house with a covered porch, a garage, and a front yard with potted plants.

1. 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, (176 reviews)
"This is a really lovely place to stay. Clean and very comfortable with lovely hosts."
United Kingdom
Lucinda
$107 nightly
The price is $117
Nov 5 - Nov 6
Total with taxes and fees
Large suite/private bath/private entrance on quiet street near Thomas Bay
A modern kitchen with a central island, bar stools, a dining table, and a built-in oven.

2. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (129 reviews)
"Really nice room and location"
United States
Victoria
$263 nightly
The price is $280
Nov 16 - Nov 17
Total with taxes and fees
The Weldon Hotel
A multi-story building with a stone facade, large windows, and a corner entrance.

3. Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (18 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
$367 nightly
The price is $400
Dec 1 - Dec 2
Total with taxes and fees
Evalina Hotel
A backyard with a wooden deck, a small staircase, and a wooden fence.

4. Great suburban location close to town!

Great suburban location close to town!
Deering Center
9.4 out of 10, Exceptional, (6 reviews)
"We were staying here for the sake of being able to see a show at Good Theater. The theater itself ended up being within walking distance, and same for a few different places to eat! This worked out great for our plans :)"
United States
Kaley
$77 nightly
The price is $78
Nov 9 - Nov 10
Total with taxes and fees
Great suburban location close to town!
A bedroom with a wooden bed, a nightstand, a bench, a chair, and a ceiling with a light fixture.

5. Studio Apartment near downtown Walkable!

Studio Apartment near downtown Walkable!
West Bayside
8.2 out of 10, Very good, (25 reviews)
"Location was convenient to everything and building was super secure."
United States
Rose
$121 nightly
The price is $122
Nov 12 - Nov 13
Total with taxes and fees
Studio Apartment near downtown Walkable!
A living room with a sofa, armchairs, a coffee table, and a potted plant.

6. Beautiful 1st Floor Apartment & Amazing Shower

Beautiful 1st Floor Apartment & Amazing Shower
Parkside
8.6 out of 10, Excellent, (34 reviews)
"This was a clean and good location for our stay. "
United States
Jocelyn R.
$142 nightly
The price is $155
Nov 8 - Nov 9
Total with taxes and fees
Beautiful 1st Floor Apartment & Amazing Shower
A gym with treadmills, elliptical machines, and exercise balls.

7. 1-bedroom hotel suites in Scarborough with essentially stocked kitchens.

1-bedroom hotel suites in Scarborough with essentially stocked kitchens.
South Portland
9.2 out of 10, Wonderful, (22 reviews)
"We really appreciated our stay!"
United States
Anonymous traveler
$110 nightly
The price is $120
Nov 6 - Nov 7
Total with taxes and fees
1-bedroom hotel suites in Scarborough with essentially stocked kitchens.
A living room with a sofa, armchair, and glass coffee table. There are two lamps on side tables and a window with curtains.

8. Portland 1-bedroom with enclosed porch & parking

Portland 1-bedroom with enclosed porch & parking
Deering Center
8.0 out of 10, Very good, (17 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.
$75 nightly
The price is $76
Nov 5 - Nov 6
Total with taxes and fees
Portland 1-bedroom with enclosed porch & parking
A kitchen with wooden cabinets, a stainless steel sink, and a potted plant.

9. Bright & Spacious Apartment with Amazing Shower

Bright & Spacious Apartment with Amazing Shower
Parkside
8.6 out of 10, Excellent, (29 reviews)
"Lovely apartment, in a pristine location. Very spacious and comfortable all around. Highly recommended this place for your next stay in Portland, Maine!"
United States
Gintare V.
$149 nightly
The price is $163
Nov 10 - Nov 11
Total with taxes and fees
Bright & Spacious Apartment with Amazing Shower
A kitchen with a wooden countertop, a black kettle, a vase with flowers, and a small wire basket.

10. 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.
$192 nightly
The price is $209
Nov 8 - Nov 9
Total with taxes and fees
Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland
A brick wall with a logo and the text 'THE SEND BREWING CO.'

11. Peaceful & minutes from Old Port w/private parking

Peaceful & minutes from Old Port w/private parking
Knightville
9.8 out of 10, Exceptional, (13 reviews)
"Cute, convenient spot!"
United States
Kelly S.
$240 nightly
The price is $264
Nov 5 - Nov 6
Total with taxes and fees
Peaceful & minutes from Old Port w/private parking
A house with a wooden staircase leading to a door marked with the number 50.

12. 1200 Sq Ft ♦ West End Gem ♦ Perfect Location

1200 Sq Ft ♦ West End Gem ♦ Perfect Location
West End
9.2 out of 10, Wonderful, (108 reviews)
"Very nice place, clean, good location. On-street parking was available. Second floor kitchen & bath, so not for those with issues with stairs, but fine for us. Would stay again!"
United States
Gary
$232 nightly
The price is $252
Nov 8 - Nov 9
Total with taxes and fees
1200 Sq Ft ♦ West End Gem ♦ Perfect Location
A brick wall with a logo and the text 'THE SEND BREWING CO.'

13. Sunny Spot with Private Parking

Sunny Spot with Private Parking
Knightville
9.8 out of 10, Exceptional, (38 reviews)
"Great property. Cute place. Note that there are very steep steps to get into the place, which is a conveyed attic."
United States
Greg Z.
$222 nightly
The price is $244
Nov 5 - Nov 6
Total with taxes and fees
Sunny Spot with Private Parking
A modern interior with a dining area, a living room, and a kitchen.

14. 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.
$135 nightly
The price is $142
Nov 10 - Nov 11
Total with taxes and fees
Studio Apartment in Freeport
A spacious dining area with a wooden table and chairs, a dark-colored sofa with a blue cushion, and a chandelier.

15. Beautiful West End Apartment by Everrow

Beautiful West End Apartment by Everrow
West End
8.8 out of 10, Excellent, (9 reviews)
"Check in was hassle free. It had all the basics and the communication with the manager was great. Beds were clean and comfy. The outside of the house was really unappealing but the inside was much better. "
United States
Tammy J.
$323 nightly
The price is $352
Nov 9 - Nov 10
Total with taxes and fees
Beautiful West End Apartment by Everrow
A staircase with white railings and wooden steps leading to a dining area with a table and chairs.

16. 1200 sq ft ♦ West End Townhouse ♦ Perfect Location

1200 sq ft ♦ West End Townhouse ♦ Perfect Location
West End
8.6 out of 10, Excellent, (64 reviews)
"Nice place, good location and very responsive host. I would definitely stay again when in Portland."
United States
Susan d.
$321 nightly
The price is $350
Nov 9 - Nov 10
Total with taxes and fees
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
A living room with a television, a wooden chest, a glass coffee table, a sofa, and a chair.

17. Walk to Old Port ♦ West End Condo ♦ Parking

Walk to Old Port ♦ West End Condo ♦ Parking
West End
9.4 out of 10, Exceptional, (97 reviews)
"Excellent property in Portland. Clean with amenities needed for any stay. Easy access to downtown. Hosts communicate exceptionally well and property is everything it promotes!"
United States
Adam Y.
$308 nightly
The price is $336
Nov 8 - Nov 9
Total with taxes and fees
Walk to Old Port ♦ West End Condo ♦ Parking
A modern living room with a sofa, a coffee table, a TV, and a window with blinds.

18. Pine Point Beach private, quaint, charming studio.

Pine Point Beach private, quaint, charming studio.
Blue Point
10.0 out of 10, Exceptional, (46 reviews)
"Great vacation rental. Convenient to all we wanted to do in the area. Very clean and very livable property!"
United States
Thomas M.
$266 nightly
The price is $290
Dec 1 - Dec 2
Total with taxes and fees
Pine Point Beach private, quaint, charming studio.
A spacious restaurant with wooden tables and benches, large windows, and hanging pendant lights.

19. Charming West End Hideaway. Private Parking

Charming West End Hideaway. Private Parking
West End
10.0 out of 10, Exceptional, (61 reviews)
"Great stay. The apartment is cute, clean, and in a perfect location. Parking was easy, and the mattress was very comfortable. Would definitely stay here again."
United States
Victoria M.
$232 nightly
The price is $257
Nov 10 - Nov 11
Total with taxes and fees
Charming West End Hideaway. Private Parking
A grassy area with a picnic table and chairs, a body of water, and two trees in the background.

20. Sunset Hideaway on Bailey Island

Sunset Hideaway on Bailey Island
Harpswell
9.0 out of 10, Wonderful, (8 reviews)
"The views from the home were amazing! The home was cozy and had everything we needed for our stay. The host was great with communication and quick to reply. We were very happy with our stay and are grateful for the ability to stay here."
United States
Elizabeth M.
$176 nightly
The price is $176
Nov 9 - Nov 10
Total with taxes and fees
Sunset Hideaway on Bailey Island
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 County Hotel Reviews

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

10/10 Excellent
"Loved how relaxing it was, very close to everything!"
Dannielle 4-night trip
Posted 7 hours ago
Portland Regency Hotel & Spa

Find out more about Cumberland County

Discover your perfect Cumberland County vacation rental with Expedia

How many vacation rentals are available in Cumberland County?


Expedia has plenty of vacation rentals to choose from in and around  Cumberland County, so you’re guaranteed to find the right one for you. 


How much is a vacation rental in Cumberland County?


The selection of Cumberland County vacation rentals we have selected for you start as low as $76 per night. Entering your travel dates in the search wizard you might find even better deals!


What type of vacation rental can I get in Cumberland County?


Vacation rentals in Cumberland County come in all shapes and sizes, and your options depend on your chosen travel dates. You could entertain in a blissful vacation home, chill in a private apartment, or find family fun at a resort. Expedia offers a superb choice of Cumberland County vacation rentals to suit everyone. 


Why should I choose a vacation rental in Cumberland County?


Expedia’s vacation rentals provide cozy comforts you can sink into on your own schedule. You’ll enjoy your own space in a property with a kitchen, a pool, a garden etc. Maybe you’ll prefer somewhere with a spa or kids activities. A Cumberland County vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in. 


How do I find the best deal on a vacation rental in Cumberland County?


Find vacation rentals in Cumberland County by viewing Expedia’s latest deals, or enter your travel dates and use the filters to select by amenities, price, or rating. Dive into the reviews to get a true feeling of which is your favorite vacation rental in Cumberland County.  


What amenities are available in a vacation rental in Cumberland County?


The choice is yours! Perhaps you love cooking in a well-equipped kitchen. Or maybe a late breakfast and a swimming pool is more your thing. Of course, there’s always the treat of having your own hot tub. Expedia has a vast range of amenities in Cumberland County vacation rentals designed to suit every budget and trip type.


When is the best time to stay in a vacation rental in Cumberland County?   


Everytime is a great time to head to Cumberland County! Staying in a Cumberland County vacation rentals you will always find lots going on to keep you entertained. 


Why book a vacation rental with Expedia?


Expedia has locked in amazing deals on a huge selection of impressive vacation rentals in Cumberland County. We give you the information and inspiration you need all in one place. With so many properties to choose from, you know you can book your perfect Cumberland County vacation rental with confidence. ANd don’t forget, if you bundle with a flight or a car rental in Cumberland County, you can save even more.


Can I cancel my vacation rental through Expedia?  


Yes, you can cancel or change your Cumberland County vacation rental by contacting your property manager directly. Contact details are easy to find on your itinerary in Trips. For more information, check out our Customer Service Portal and we’ll help you get everything sorted.