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

Holiday Rentals in Cumberland County

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Top Cities in Cumberland County

A crowded beach with people sunbathing and swimming, surrounded by houses and lush green hills.
Holiday RentalsHoliday Rentals

Scarborough

Scarborough

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, (117 reviews)
"Really nice room and location"
United States
Victoria
The price is €421
includes taxes & fees
21 Sept - 22 Sept
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, (11 reviews)
"Truly a wonderful place with an unbeatable location. Highly recommend for a visit to Portland."
United States
Eric
The price is €698
includes taxes & fees
13 Sept - 14 Sept
Evalina Hotel

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, (111 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.
Ocean View East End Studio in a Historic Victorian
A modern loft with a large arched window, a glass dining table, and a flat-screen TV mounted on the brick wall.

4. Downtown Penthouse Suite - Stunning Harbor Views

Downtown Penthouse Suite - Stunning Harbor Views
Downtown Portland
10.0 out of 10, Exceptional, (237 reviews)
"We loved it!"
United States
Joshua H.
The price is €989
includes taxes & fees
4 Oct - 5 Oct
Downtown Penthouse Suite - Stunning Harbor Views
A yurt with a bed, a desk, and a view of the outdoors.

5. 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 €522
includes taxes & fees
1 Oct - 2 Oct
Fortland Island Campground
A modern apartment with a living room, dining area, and kitchen.

6. 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, (85 reviews)
"Lovely stay at a lovely place!"
United States
Bunny B.
The price is €520
includes taxes & fees
13 Sept - 14 Sept
2 Bedroom Apartment on Top Floor in Portland's West End
A two-story house with a covered porch, a garage, and a front yard with potted plants.

7. 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, (167 reviews)
"What a beautiful place to stay. Jeff and Susan made your stay a very special experience."
United States
DENESE
The price is €153
includes taxes & fees
15 Sept - 16 Sept
Large suite/private bath/private entrance on quiet street near Thomas Bay
A room with a wooden bench, a red guitar, and a plant on a table.

8. 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)
"Everything was great! Excellent location, clean and great communication. Thank you!"
United States
Stephanie W.
The price is €680
includes taxes & fees
9 Sept - 10 Sept
Prime Old Port 3BR • Free Parking • Sleeps 8
A theater with a marquee reading "STATE" and a classic architectural design.

9. Luxury Condo Downtown Portland Old Port

Luxury Condo Downtown Portland Old Port
Downtown Portland
9.4 out of 10, Exceptional, (22 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 €389
includes taxes & fees
9 Sept - 10 Sept
Luxury Condo Downtown Portland Old Port
A kitchen with a wooden countertop, a black kettle, a vase with flowers, and a small wire basket.

10. 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, (27 reviews)
"Great place! We would definitely return if we were in the area."
United States
Preston
The price is €257
includes taxes & fees
5 Oct - 6 Oct
Charming Studio apartment with WiFi, AC in welcoming Portland
A house with a wooden staircase leading to a door marked with the number 50.

11. 1200 Sq Ft ♦ West End Gem ♦ Perfect Location

1200 Sq Ft ♦ West End Gem ♦ Perfect Location
West End
9.2 out of 10, Wonderful, (106 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
A two-story house with a balcony, a covered patio, and a fenced yard.

12. The Globe House on Munjoy Hill - Walk to Breweries

The Globe House on Munjoy Hill - Walk to Breweries
Munjoy Hill
10.0 out of 10, Exceptional, (105 reviews)
"Everything was as advertised; great accommodations!"
United States
Richard D.
The price is €505
includes taxes & fees
15 Sept - 16 Sept
The Globe House on Munjoy Hill - Walk to Breweries
A modern living room with a large sectional sofa, a fireplace, and large windows offering a city view.

13. Waterfront Two Master Suite Penthouse with Rooftop

Waterfront Two Master Suite Penthouse with Rooftop
Downtown Portland
10.0 out of 10, Exceptional, (200 reviews)
"Great property. It was clean, comfortable, and the location was amazing"
United States
Jaylene G.
Waterfront Two Master Suite Penthouse with Rooftop
A wide beach with people walking and a few dogs.

14. 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, (4 reviews)
"Great place, so close to everything and a clean, quiet spot to sleep."
United States
Dan K.
THE RALEIGH BnB APARTMENT SELF CHECK-IN / Free Off-Street Parking
A spacious living room with a large window, a fireplace, and a view of a marina.

15. Penthouse Two Master Waterfront Suite with Rooftop

Penthouse Two Master Waterfront Suite with Rooftop
Downtown Portland
10.0 out of 10, Exceptional, (268 reviews)
"This was one of the most spectacular places we have ever stayed. The views are amazing and the place is just incredible. We really look forward to our next visit!"
United States
Daryl R.
Penthouse Two Master Waterfront Suite with Rooftop
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 €615
includes taxes & fees
4 Oct - 5 Oct
Portland’s Best Ocean Views from a 40-Foot Private Deck
A modern kitchen with a central island, two stools, skylights, and a view of the outdoors.

17. East End Guesthouse

East End Guesthouse
Munjoy Hill
10.0 out of 10, Exceptional, (3 reviews)
"Fabulous stay!! Felt like we were living in a Crate & Barrel catalog. Great location. "
United States
Ashleigh F.
East End Guesthouse
A balcony with wooden flooring and a view of the cityscape.

18. Old Port Penthouse Suite - Amazing Harbor Views

Old Port Penthouse Suite - Amazing Harbor Views
Downtown Portland
10.0 out of 10, Exceptional, (253 reviews)
"Amazing property with the perfect location! Highly recommend and would definitely stay here again."
United States
Lisa G.
Old Port Penthouse Suite - Amazing Harbor Views
A modern living room with a wooden dining table, chairs, a TV, and a bookshelf.

19. 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, (42 reviews)
"Exactly as described and in one of the loveliest parts of Portland! Communication with owner was smooth and seamless. Perfect place to get to multiple places of interest in this charming city."
United States
Emily W.
East end. Walk to food, beer and downtown fun.
A room with a wooden floor, a round table, two chairs, a sofa, and a patterned rug.

20. NEW 1 BDR-Heart of Munjoy Hill

NEW 1 BDR-Heart of Munjoy Hill
Munjoy Hill
9.8 out of 10, Exceptional, (8 reviews)
"Great location within walking distance to activities, food, the bay, etc. "
United States
Anne D.
NEW 1 BDR-Heart of Munjoy Hill
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

Hyatt Place Portland Downtown - Old Port Square

Hyatt Place Portland Downtown - Old Port Square

10/10 Excellent
"Great Staff. Good Breakfast. We will return."
Christopher 1-night trip
Posted 2 hours ago
Hyatt Place Portland Downtown - Old Port Square

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, apart-hotels, 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 €143 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.