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

Cumberland County Holiday Rentals

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Top Cities in Cumberland County

A flowing river with large rocks, surrounded by trees and a snowy bank.
Holiday RentalsHoliday Rentals

Raymond

Raymond

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, (121 reviews)
"Really nice room and location"
United States
Victoria
The price is NZ$832
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, (12 reviews)
"Truly a wonderful place with an unbeatable location. Highly recommend for a visit to Portland."
United States
Eric
The price is NZ$1,305
includes taxes & fees
25 Oct - 26 Oct
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, (112 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 NZ$814
includes taxes & fees
27 Sept - 28 Sept
Ocean View East End Studio in a Historic Victorian
A grand room with ornate chandeliers, a fireplace, and classical furniture.

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

Historic Home in the West End. Private Parking.
West End
9.8 out of 10, Exceptional, (68 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 NZ$691
includes taxes & fees
18 Oct - 19 Oct
Historic Home in the West End. Private Parking.
A modern apartment with a living room, dining area, and kitchen.

5. 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 NZ$850
includes taxes & fees
28 Sept - 29 Sept
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".

6. Glorious getaway on Portland's Eastern Promenade.

Glorious getaway on Portland's Eastern Promenade.
Munjoy Hill
9.8 out of 10, Exceptional, (184 reviews)
"Wonderful experience with exceptional hosts!"
United States
Cynthia
The price is NZ$825
includes taxes & fees
28 Sept - 29 Sept
Glorious getaway on Portland's Eastern Promenade.
A modern loft with a large arched window, a glass dining table, and a flat-screen TV mounted on the brick wall.

7. 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.
Downtown Penthouse Suite - Stunning Harbor Views
A street lined with buildings, one with a red door and a sign that reads "MINATO".

8. Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (148 reviews)
"Owner was so accommodating!"
United States
Kiernan
The price is NZ$501
includes taxes & fees
20 Oct - 21 Oct
Adorable Portland getaway on the Eastern Promenade
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 NZ$759
includes taxes & fees
25 Oct - 26 Oct
Luxury Condo Downtown Portland Old Port
A modern kitchen with a central island, bar stools, pendant lighting, and a large refrigerator.

10. Harborview - Curated East End Escape w/ Parking

Harborview - Curated East End Escape w/ Parking
Munjoy Hill
10.0 out of 10, Exceptional, (14 reviews)
"5 star in every way"
United States
Doug F.
Harborview - Curated East End Escape w/ Parking
A room with a wooden bench, a red guitar, and a plant on a table.

11. 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 NZ$1,416
includes taxes & fees
30 Sept - 1 Oct
Prime Old Port 3BR • Free Parking • Sleeps 8
A two-story house with a covered porch, a garage, and a front yard with potted plants.

12. 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, (172 reviews)
"What a beautiful place to stay. Jeff and Susan made your stay a very special experience."
United States
DENESE
The price is NZ$286
includes taxes & fees
28 Sept - 29 Sept
Large suite/private bath/private entrance on quiet street near Thomas Bay
A garden with a stone bridge over a small stream, surrounded by various plants and flowers.

13. Peaceful Oasis on Munjoy Hill 2nd flr 3BR parking

Peaceful Oasis on Munjoy Hill 2nd flr 3BR parking
Munjoy Hill
9.8 out of 10, Exceptional, (7 reviews)
"10/10 would stay again Close to nice bars,restaurants, gas stations. Clean apartment. Host was very nice! "
United States
Mary C.
Peaceful Oasis on Munjoy Hill 2nd flr 3BR parking
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 price is NZ$833
includes taxes & fees
22 Oct - 23 Oct
THE RALEIGH BnB APARTMENT SELF CHECK-IN / Free Off-Street Parking
A modern kitchen with a central island, stainless steel appliances, and contemporary artwork.

15. A Peaceful Oasis on Munjoy Hill: 1st flr - 3BR + parking

A Peaceful Oasis on Munjoy Hill: 1st flr - 3BR + parking
Munjoy Hill
10.0 out of 10, Exceptional, (8 reviews)
"This apartment was perfect. Great location, spotlessly clean, very spacious rooms and comfortable beds. Thank you Ani for letting us stay in your lovely apartment. "
United States
Lauren
A Peaceful Oasis on Munjoy Hill: 1st flr - 3BR + parking
A kitchen with a wooden countertop, a black kettle, a vase with flowers, and a small wire basket.

16. 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, (28 reviews)
"Great place! We would definitely return if we were in the area."
United States
Preston
The price is NZ$407
includes taxes & fees
20 Oct - 21 Oct
Charming Studio apartment with WiFi, AC in welcoming Portland
A black console table with a mirror above it, a lamp, and a potted plant beside it.

17. 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 NZ$608
includes taxes & fees
27 Sept - 28 Sept
Peaceful & minutes from the Old Port with private parking
A deck with wicker furniture and a view of the water.

18. 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 NZ$1,259
includes taxes & fees
4 Oct - 5 Oct
Portland’s Best Ocean Views from a 40-Foot Private Deck
A two-story house with a balcony, a covered patio, and a fenced yard.

19. 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, (108 reviews)
"Everything was as advertised; great accommodations!"
United States
Richard D.
The price is NZ$1,167
includes taxes & fees
6 Oct - 7 Oct
The Globe House on Munjoy Hill - Walk to Breweries
A wooden bench on a rocky shore overlooking a calm body of water.

20. City Amenities, Casco Bay Sunrises and Natural Beauty

City Amenities, Casco Bay Sunrises and Natural Beauty
East Deering
9.8 out of 10, Exceptional, (133 reviews)
"Wonderful place! Owner very responsible! Would stay again! Great choice for place to stay away from home."
United States
Arlene L.
City Amenities, Casco Bay Sunrises and Natural Beauty
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

Inn at St John Portland In-Town

Inn at St John Portland In-Town

8/10 Good
"Everything was good."
Robert 1-night trip
Posted less than an hour ago
Inn at St John Portland In-Town

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$188 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.