Cumberland County Holiday Rentals

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Top cities in Cumberland County

A lighthouse and houses on a rocky coastline with the ocean in the background.
Vacation Rentals

Portland

Portland

Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Cumberland County holiday 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
The price is NZ$210
includes taxes & fees
1 Dec - 2 Dec
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, (131 reviews)
"It was so spacious, kitchen area was well kept and they have QR codes to help travels understand how to use certain things"
United States
Branden
The price is NZ$504
includes taxes & fees
2 Dec - 3 Dec
The Weldon Hotel
A backyard with a wooden deck, a small staircase, and a wooden fence.

3. 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
The price is NZ$141
includes taxes & fees
10 Nov - 11 Nov
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.

4. Studio Apartment near downtown Walkable!

Studio Apartment near downtown Walkable!
West Bayside
8.2 out of 10, Very good, (27 reviews)
"Location was convenient to everything and building was super secure."
United States
Rose
The price is NZ$220
includes taxes & fees
12 Nov - 13 Nov
Studio Apartment near downtown Walkable!
A living room with a sofa, armchair, and glass coffee table. There are two lamps on side tables and a window with curtains.

5. Portland 1-bedroom with enclosed porch & parking

Portland 1-bedroom with enclosed porch & parking
Deering Center
7.8 out of 10, Good, (18 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.
The price is NZ$147
includes taxes & fees
10 Nov - 11 Nov
Portland 1-bedroom with enclosed porch & parking
A brick wall with a logo and the text 'THE SEND BREWING CO.'

6. 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.
The price is NZ$367
includes taxes & fees
10 Nov - 11 Nov
Sunny Spot with Private Parking
A living room with a sofa, armchairs, a coffee table, and a potted plant.

7. Beautiful 1st Floor Apartment & Amazing Shower

Beautiful 1st Floor Apartment & Amazing Shower
Parkside
8.6 out of 10, Excellent, (35 reviews)
"This was a clean and good location for our stay. "
United States
Jocelyn R.
The price is NZ$259
includes taxes & fees
18 Nov - 19 Nov
Beautiful 1st Floor Apartment & Amazing Shower
A multi-story building with a stone facade, large windows, and a corner entrance.

8. Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (19 reviews)
"Truly a wonderful place with an unbeatable location. Highly recommend for a visit to Portland."
United States
Eric
The price is NZ$724
includes taxes & fees
6 Dec - 7 Dec
Evalina Hotel
A gym with treadmills, elliptical machines, and exercise balls.

9. 1-bedroom hotel suites in Scarborough with essentially stocked kitchens.

1-bedroom hotel suites in Scarborough with essentially stocked kitchens.
South Portland
9.4 out of 10, Exceptional, (23 reviews)
"We really appreciated our stay!"
United States
Anonymous traveller
The price is NZ$216
includes taxes & fees
11 Nov - 12 Nov
1-bedroom hotel suites in Scarborough with essentially stocked kitchens.
A brick wall with a logo and the text 'THE SEND BREWING CO.'

10. 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.
The price is NZ$440
includes taxes & fees
10 Nov - 11 Nov
Peaceful & minutes from Old Port w/private parking
A kitchen with wooden cabinets, a stainless steel sink, and a potted plant.

11. 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.
The price is NZ$294
includes taxes & fees
10 Nov - 11 Nov
Bright & Spacious Apartment with Amazing Shower
A kitchen with a wooden countertop, a black kettle, a vase with flowers, and a small wire basket.

12. 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)
"Everything you need, very clean, close to the water and easily walkable to many things. Would definitely stay again!"
United States
Ryan B.
The price is NZ$389
includes taxes & fees
10 Nov - 11 Nov
Charming Studio Retreat with Queen bed, WiFi, and AC in welcoming Portland
A spacious restaurant with wooden tables and benches, large windows, and hanging pendant lights.

13. Historic Home in the West End. Private Parking.

Historic Home in the West End. Private Parking.
West End
10.0 out of 10, Exceptional, (78 reviews)
"The location is excellent. We were very happy to have onsite parking. The apartment is lovely, nice touches all around. The hosts were easy to work with and quite pleasant. I would definitely recommend the stay."
United States
Linda
The price is NZ$515
includes taxes & fees
18 Nov - 19 Nov
Historic Home in the West End. Private Parking.
A door with a screen, a bird statue, and a house number sign.

14. 1200 sq ft ♦ West End Gem ♦ Steps from Old Port

1200 sq ft ♦ West End Gem ♦ Steps from Old Port
West End
9.2 out of 10, Wonderful, (110 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
The price is NZ$465
includes taxes & fees
18 Nov - 19 Nov
1200 sq ft ♦ West End Gem ♦ Steps from Old Port
A staircase with white railings and wooden steps leading to a dining area with a table and chairs.

15. 1200 sq ft ♦ West End Townhouse ♦ Walk to Old Port

1200 sq ft ♦ West End Townhouse ♦ Walk to Old Port
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.
The price is NZ$648
includes taxes & fees
8 Dec - 9 Dec
1200 sq ft ♦ West End Townhouse ♦ Walk to Old Port
A modern interior with a dining area, a living room, and a kitchen.

16. 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.
The price is NZ$240
includes taxes & fees
10 Nov - 11 Nov
Studio Apartment in Freeport
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)
"Was great for our few days in Portland! Having a designated parking space was great and the location was convenient for everything we wanted to do."
United States
Britney G.
The price is NZ$627
includes taxes & fees
10 Nov - 11 Nov
Walk to Old Port ♦ West End Condo ♦ Parking
A spacious dining area with a wooden table and chairs, a dark-colored sofa with a blue cushion, and a chandelier.

18. 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.
The price is NZ$680
includes taxes & fees
7 Dec - 8 Dec
Beautiful West End Apartment by Everrow
A grassy area with a picnic table and chairs, a body of water, and two trees in the background.

19. 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.
The price is NZ$342
includes taxes & fees
16 Nov - 17 Nov
Sunset Hideaway on Bailey Island
A cabin with two chairs facing a fire pit, surrounded by trees.

20. Cabin w/ bath + kitchenette | Hot tub add-on - 03

Cabin w/ bath + kitchenette | Hot tub add-on - 03
Freeport
9.8 out of 10, Exceptional, (10 reviews)
"A lovely glamping facility with several different types of structure in a quiet, wooded area just a couple miles from downtown Freeport. They've built a beautiful spa with sauna, cold plunge, hot tub, and soaking pool, the unit we stayed in was bright and airy, had an outdoor fire pit. We stayed three nights, will definitely stop here again!"
United States
Kirt v.
The price is NZ$498
includes taxes & fees
10 Nov - 11 Nov
Cabin w/ bath + kitchenette | Hot tub add-on - 03
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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Find holiday rentals that suit your style

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Top Cumberland County Hotel Reviews

A house with a sign for The James Place Inn, indicating a vacancy.
The James Place Inn B&B

The James Place Inn B&B

The James Place Inn B&B
Freeport

10/10 Excellent

Fantastic location run by a delightful family team offering all the ‘home’ comforts you might not expect at other B & Bs. Easy walking to the main town attractions including eateries. Great personalised breakfast with top up muffins and other treats throughout. Highly recommend this location for return visits.
Australia
Anonymous traveller
Reviewed July 6, 2019
The James Place Inn B&B

Find out more about Cumberland County

Everything you need to know about Cumberland County holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Cumberland County holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cumberland County holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Cumberland County holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cumberland County. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Cumberland County holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cumberland County holiday rentals we have selected for you start as low as NZ$140 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Cumberland County rentals

At Expedia, we put the best Cumberland County holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Cumberland County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cumberland County holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cumberland County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.