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

Cumberland County Holiday Rentals

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Our top choices for Cumberland County holiday rentals

A modern kitchen with a central island, bar stools, a dining table, and a built-in oven.

1. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (122 reviews)
"Really nice room and location"
United States
Victoria
The price is AU$647
includes taxes & fees
25 Oct - 26 Oct
The Weldon Hotel
A multi-story building with a stone facade, large windows, and a corner entrance.

2. Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (13 reviews)
"Truly a wonderful place with an unbeatable location. Highly recommend for a visit to Portland."
United States
Eric
The price is AU$973
includes taxes & fees
27 Oct - 28 Oct
Evalina Hotel
Exterior

3. 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, (113 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 AU$648
includes taxes & fees
13 Oct - 14 Oct
Ocean View East End Studio in a Historic Victorian
A kitchen with a wooden countertop, a black kettle, a vase with flowers, and a small wire basket.

4. Charming Studio apartment with WiFi, AC in welcoming Portland

Charming Studio apartment with WiFi, AC in welcoming Portland
Munjoy Hill
9.6 out of 10, Exceptional, (29 reviews)
"Loved this spot and would stay again. Had everything you needed and a great location. Cute little attic spot but nice and cool."
United States
Emily N.
The price is AU$372
includes taxes & fees
20 Oct - 21 Oct
Charming Studio apartment with WiFi, AC in welcoming Portland
A grand room with ornate chandeliers, a fireplace, and classical furniture.

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

Historic Home in the West End. Private Parking.
West End
10.0 out of 10, Exceptional, (71 reviews)
"This home was a unique and wonderful stop on a trip through Portland. The historical charm really shines through. Jennifer left very clear instructions throughout the apartment on how everything worked. And the parking and location were very convenient. I would not hesitate to stay here again!"
United States
Daina
The price is AU$557
includes taxes & fees
27 Oct - 28 Oct
Historic Home in the West End. Private Parking.
A street lined with buildings, one with a red door and a sign that reads "MINATO".

6. Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (149 reviews)
"Owner was so accommodating!"
United States
Kiernan
The price is AU$416
includes taxes & fees
21 Oct - 22 Oct
Adorable Portland getaway on the Eastern Promenade
A beach with a wooden chair and a small building in the background.

7. Arlie`s Digs! - One Block To Willard Beach!

Arlie`s Digs! - One Block To Willard Beach!
Willard Beach
10.0 out of 10, Exceptional, (70 reviews)
"Beautiful place, perfect location! "
United States
Melissa M.
The price is AU$663
includes taxes & fees
26 Oct - 27 Oct
Arlie`s Digs! - One Block To Willard Beach!
A modern apartment with a living room, dining area, and kitchen.

8. 2 Bedroom Apartment on Top Floor in Portland's West End

2 Bedroom Apartment on Top Floor in Portland's West End
West End
10.0 out of 10, Exceptional, (88 reviews)
"The rooftop deck makes the climb worth it. Everything was clean neat and organized. Great beds. Communication was fast and friendly. Thanks for a great stay. "
United States
TODD H.
The price is AU$673
includes taxes & fees
18 Oct - 19 Oct
2 Bedroom Apartment on Top Floor in Portland's West End
A street lined with buildings, one with a red door and a sign that reads "MINATO".

9. Glorious getaway on Portland's Eastern Promenade.

Glorious getaway on Portland's Eastern Promenade.
Munjoy Hill
9.8 out of 10, Exceptional, (185 reviews)
"Wonderful experience with exceptional hosts!"
United States
Cynthia
The price is AU$650
includes taxes & fees
1 Oct - 2 Oct
Glorious getaway on Portland's Eastern Promenade.
A theater with a marquee reading "STATE" and a classic architectural design.

10. Luxury Condo Downtown Portland Old Port

Luxury Condo Downtown Portland Old Port
Downtown Portland
9.4 out of 10, Exceptional, (23 reviews)
"Portland is awesome, the house was in a great location, nice neighborhood and really conveniently located to an abundance of restaurants"
United States
Doug T.
The price is AU$558
includes taxes & fees
27 Oct - 28 Oct
Luxury Condo Downtown Portland Old Port
A black console table with a mirror above it, a lamp, and a potted plant beside it.

11. 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, (13 reviews)
"Cute, convenient spot!"
United States
Kelly S.
The price is AU$557
includes taxes & fees
19 Oct - 20 Oct
Peaceful & minutes from the Old Port with private parking
A wide beach with people walking and a few dogs.

12. 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, (5 reviews)
"Great place, so close to everything and a clean, quiet spot to sleep."
United States
Dan K.
The price is AU$683
includes taxes & fees
28 Oct - 29 Oct
THE RALEIGH BnB APARTMENT SELF CHECK-IN / Free Off-Street Parking
A modern living room with a sofa, a coffee table, a TV, and a window with blinds.

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

Pine Point Beach private, quaint, charming studio.
Blue Point
10.0 out of 10, Exceptional, (44 reviews)
"Great vacation rental. Convenient to all we wanted to do in the area. Very clean and very livable property!"
United States
Thomas M.
The price is AU$470
includes taxes & fees
30 Sept - 1 Oct
Pine Point Beach private, quaint, charming studio.
A restaurant window with 'OYSTER CO. EVENTIDE' signage, indicating a raw bar, chowders, and cocktails.

14. Modern & Sunny House Steps from the Promenade.

Modern & Sunny House Steps from the Promenade.
Munjoy Hill
10.0 out of 10, Exceptional, (44 reviews)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
The price is AU$796
includes taxes & fees
12 Oct - 13 Oct
Modern & Sunny House Steps from the Promenade.
A room with a wooden bench, a red guitar, and a plant on a table.

15. Prime Old Port 3BR • Free Parking • Sleeps 8

Prime Old Port 3BR • Free Parking • Sleeps 8
Downtown Portland
9.8 out of 10, Exceptional, (164 reviews)
"Clean and comfortable stay in great location! "
United States
Juliet S.
The price is AU$1,144
includes taxes & fees
21 Oct - 22 Oct
Prime Old Port 3BR • Free Parking • Sleeps 8
A deck with wicker furniture and a view of the water.

16. Portland’s Best Ocean Views from a 40-Foot Private Deck

Portland’s Best Ocean Views from a 40-Foot Private Deck
Munjoy Hill
9.6 out of 10, Exceptional, (31 reviews)
"Beautiful location with easy walk to downtown. "
United States
Megan T.
The price is AU$991
includes taxes & fees
27 Oct - 28 Oct
Portland’s Best Ocean Views from a 40-Foot Private Deck
A building with a brick facade, large windows, and a covered outdoor seating area.

17. Spacious 3 BR in Portland's Libbytown!

Spacious 3 BR in Portland's Libbytown!
Portland
9.4 out of 10, Exceptional, (61 reviews)
"Very clean and has a lot of amenities"
United States
Philip
The price is AU$687
includes taxes & fees
30 Sept - 1 Oct
Spacious 3 BR in Portland's Libbytown!
A modern living room with a wooden dining table, chairs, a TV, and a bookshelf.

18. East end. Walk to food, beer and downtown fun.

East end. Walk to food, beer and downtown fun.
Munjoy Hill
9.8 out of 10, Exceptional, (44 reviews)
"Very comfortable and stocked well. Lacked for nothing and able to walk to most places. Host checked in which was very nice. Enjoyed Portland."
United States
sheila g.
The price is AU$514
includes taxes & fees
27 Oct - 28 Oct
East end. Walk to food, beer and downtown fun.
A gym with treadmills, elliptical machines, and exercise balls.

19. 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, (19 reviews)
"We really appreciated our stay!"
United States
Anonymous traveller
The price is AU$257
includes taxes & fees
30 Sept - 1 Oct
1-bedroom hotel suites in Scarborough with essentially stocked kitchens.
A house with a wooden staircase leading to a door marked with the number 50.

20. 1200 Sq Ft ♦ West End Gem ♦ Perfect Location

1200 Sq Ft ♦ West End Gem ♦ Perfect Location
West End
9.2 out of 10, Wonderful, (107 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
1200 Sq Ft ♦ West End Gem ♦ Perfect Location
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

Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG

10/10 Excellent
"It was convenient"
Matthew 2-night trip
Posted 5 hours ago
Holiday Inn Portland-By the Bay by IHG

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 favourite 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 depend 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 chosen for you start as low as AU$141 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.