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 HK$1,651
HK$2,388 total
includes taxes & fees
2 Nov - 3 Nov
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 HK$2,622
HK$4,035 total
includes taxes & fees
3 Nov - 4 Nov
Evalina Hotel
A grand room with ornate chandeliers, a fireplace, and classical furniture.

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

Historic Home in the West End. Private Parking.
West End
10.0 out of 10, Exceptional, (72 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 HK$1,781
HK$2,951 total
includes taxes & fees
1 Nov - 2 Nov
Historic Home in the West End. Private Parking.
A beach with a wooden chair and a small building in the background.

4. 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 HK$1,890
HK$4,070 total
includes taxes & fees
26 Oct - 27 Oct
Arlie`s Digs! - One Block To Willard Beach!
A kitchen with a wooden countertop, a black kettle, a vase with flowers, and a small wire basket.

5. 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 HK$981
HK$1,788 total
includes taxes & fees
23 Oct - 24 Oct
Charming Studio apartment with WiFi, AC in welcoming Portland
Exterior

6. 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 HK$2,354
HK$3,618 total
includes taxes & fees
13 Oct - 14 Oct
Ocean View East End Studio in a Historic Victorian
A deck with wicker furniture and a view of the water.

7. 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, (32 reviews)
"Beautiful location with easy walk to downtown. "
United States
Megan T.
The price is HK$3,728
HK$5,620 total
includes taxes & fees
4 Oct - 5 Oct
Portland’s Best Ocean Views from a 40-Foot Private Deck
A theater with a marquee reading "STATE" and a classic architectural design.

8. 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 HK$1,653
HK$2,990 total
includes taxes & fees
1 Nov - 2 Nov
Luxury Condo Downtown Portland Old Port
A bedroom with a bed, a nightstand, a lamp, a door, and a staircase.

9. Great suburban location close to town!

Great suburban location close to town!
Deering Center
10.0 out of 10, Exceptional, (1 review)
"Small but cozy space, well kept, good value for the price and has all the amenities you could expect. Would be happy to stay here again."
United States
Peter H.
The price is HK$589
HK$760 total
includes taxes & fees
25 Oct - 26 Oct
Great suburban location close to town!
A room with a wooden bench, a red guitar, and a plant on a table.

10. 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 HK$2,816
HK$6,439 total
includes taxes & fees
12 Oct - 13 Oct
Prime Old Port 3BR • Free Parking • Sleeps 8
A modern apartment with a living room, dining area, and kitchen.

11. 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 HK$1,954
HK$3,755 total
includes taxes & fees
18 Oct - 19 Oct
2 Bedroom Apartment on Top Floor in Portland's West End
A gray house with a black front door, white trim, and a number 70 sign.

12. Vintage Maine & Modern Convenience in Portlands Exclusive East End

Vintage Maine & Modern Convenience in Portlands Exclusive East End
Munjoy Hill
9.8 out of 10, Exceptional, (59 reviews)
"The apartment is very comfortable with everything we needed We loved the quiet neighborhood and the location was really great within walking distance to both the beach area and downtown shops & restaurants."
United States
maureen
Vintage Maine & Modern Convenience in Portlands Exclusive East End
A modern bar area with a counter, stools, and hanging lights.

13. West End Bright Spot with Parking.

West End Bright Spot with Parking.
West End
10.0 out of 10, Exceptional, (25 reviews)
"The space was pristine, comfortable, homey with an excellent location situated to shops and restaurants. Jennifer was a welcoming and warm host and we had no issues at all during our stay!"
United States
Luke E.
The price is HK$1,389
HK$2,481 total
includes taxes & fees
2 Nov - 3 Nov
West End Bright Spot with Parking.
A street lined with buildings, one with a red door and a sign that reads "MINATO".

14. 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 HK$1,389
HK$2,241 total
includes taxes & fees
20 Oct - 21 Oct
Adorable Portland getaway on the Eastern Promenade
A bedroom with a wooden bed, a nightstand, a bench, a chair, and a ceiling with a light fixture.

15. Studio Apartment near downtown Walkable!

Studio Apartment near downtown Walkable!
West Bayside
8.4 out of 10, Very good, (21 reviews)
"I will admit the location and surrounding areas are a bit sketchy, but, once inside, we felt super secure. There are multiple doors and gates with locks to ensure safety. Place was clean and had everything we needed for a quick stay."
United States
Krysta
The price is HK$618
HK$1,181 total
includes taxes & fees
1 Nov - 2 Nov
Studio Apartment near downtown Walkable!
A garden with a stone bridge over a small stream, surrounded by various plants and flowers.

16. 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.
The price is HK$1,747
HK$3,256 total
includes taxes & fees
3 Nov - 4 Nov
Peaceful Oasis on Munjoy Hill 2nd flr 3BR parking
A living room with a sofa, armchairs, a coffee table, and a potted plant.

17. Beautiful 1st Floor Apartment & Amazing Shower

Beautiful 1st Floor Apartment & Amazing Shower
Parkside
9.0 out of 10, Wonderful, (32 reviews)
"This was a clean and good location for our stay. "
United States
Jocelyn R.
The price is HK$879
HK$1,625 total
includes taxes & fees
7 Oct - 8 Oct
Beautiful 1st Floor Apartment & Amazing Shower
A street lined with buildings, one with a red door and a sign that reads "MINATO".

18. Glorious getaway on Portland's Eastern Promenade.

Glorious getaway on Portland's Eastern Promenade.
Munjoy Hill
9.8 out of 10, Exceptional, (187 reviews)
"Wonderful experience with exceptional hosts!"
United States
Cynthia
The price is HK$2,331
HK$3,635 total
includes taxes & fees
14 Oct - 15 Oct
Glorious getaway on Portland's Eastern Promenade.
A room with a wooden floor, a round table, two chairs, a sofa, and a patterned rug.

19. NEW 1 BDR-Heart of Munjoy Hill

NEW 1 BDR-Heart of Munjoy Hill
Munjoy Hill
10.0 out of 10, Exceptional, (12 reviews)
"Lovely property - exceptionally clean and really well equipped with little touches that made it even better. Great location - up a bit of a hill but near Washington Ave and nice little coffee shops and restaurants. Great communication from the host and a very comfortable stay."
United Kingdom
Kate
The price is HK$1,562
HK$3,276 total
includes taxes & fees
5 Oct - 6 Oct
NEW 1 BDR-Heart of Munjoy Hill
A hallway leading to a bedroom with a bed, a desk, and a chair. There is a framed picture on the wall and a bench in the corner.

20. Industrial Farmhouse Chic in Portland`s Most Desirable Neighborhood

Industrial Farmhouse Chic in Portland`s Most Desirable Neighborhood
Munjoy Hill
9.8 out of 10, Exceptional, (44 reviews)
"Beautiful apartment. Great location. Very comfortable and all amenities needed."
United States
Navina F.
The price is HK$2,835
HK$5,100 total
includes taxes & fees
27 Oct - 28 Oct
Industrial Farmhouse Chic in Portland`s Most Desirable Neighborhood
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

Fireside Inn & Suites Portland

Fireside Inn & Suites Portland

10/10 Excellent
"Staff are very helpful. The location is not far from freeway, so sometimes a bit noisy"
Karunia 2-night trip
Posted 1 hour ago
Fireside Inn & Suites Portland