A cityscape with a prominent church steeple, various buildings, and lush green trees.

Portland Holiday Rentals

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Portland holiday rentals

A bedroom with a wooden bed, a nightstand, a bench, a chair, and a ceiling with a light fixture.

1. Studio Apartment near downtown Walkable!

Studio Apartment near downtown Walkable!
West Bayside
8.2 out of 10, Very good, (15 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$864
HK$1,453 total
includes taxes & fees
1 Sept - 2 Sept
Studio Apartment near downtown Walkable!
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, (114 reviews)
"Really nice room and location"
United States
Victoria
The price is HK$2,309
HK$3,104 total
includes taxes & fees
1 Sept - 2 Sept
The Weldon Hotel
A house with a wooden staircase leading to a door marked with the number 50.

3. 1200 Sq Ft ♦ West End Gem ♦ Perfect Location

1200 Sq Ft ♦ West End Gem ♦ Perfect Location
West End
9.2 out of 10, Wonderful, (105 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 HK$1,506
HK$2,898 total
includes taxes & fees
23 Sept - 24 Sept
1200 Sq Ft ♦ West End Gem ♦ Perfect Location
A staircase with white railings and wooden steps leading to a dining area with a table and chairs.

4. 1200 sq ft ♦ West End Townhouse ♦ Perfect Location

1200 sq ft ♦ West End Townhouse ♦ Perfect Location
West End
8.4 out of 10, Very good, (61 reviews)
"Nice place, good location and very responsive host. I would definitely stay again when in Portland."
United States
Susan d.
The price is HK$848
HK$3,009 total
includes taxes & fees
3 Sept - 4 Sept
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
A living room with a television, a wooden chest, a glass coffee table, a sofa, and a chair.

5. Walk to Old Port ♦ West End Condo ♦ Parking

Walk to Old Port ♦ West End Condo ♦ Parking
West End
9.6 out of 10, Exceptional, (89 reviews)
"Host was very responsive, and helpful. Location is amazing for walking the city."
United States
Chris P.
The price is HK$930
HK$3,116 total
includes taxes & fees
2 Sept - 3 Sept
Walk to Old Port ♦ West End Condo ♦ Parking
A grand room with ornate chandeliers, a fireplace, and classical furniture.

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

Historic Home in the West End. Private Parking.
West End
10.0 out of 10, Exceptional, (60 reviews)
"Perfect cozy apartment for a get away! Great location that’s walkable for shopping, brunch, and coffee and less than a 15 minute drive from everything else on our itinerary!"
United States
Callie R.
The price is HK$1,780
HK$2,948 total
includes taxes & fees
7 Sept - 8 Sept
Historic Home in the West End. Private Parking.
A living room with a sofa, armchair, and glass coffee table. There are two lamps on side tables and a window with curtains.

7. Private Entrance Residential Portland

Private Entrance Residential Portland
Deering Center
8.6 out of 10, Excellent, (9 reviews)
"This was a great place to stay. Easy to get to all of our destinations. Place was clean and comfortable. Would stay here again. "
United States
Ameleah B.
The price is HK$823
HK$994 total
includes taxes & fees
25 Aug - 26 Aug
Private Entrance Residential Portland
A gym with treadmills, elliptical machines, and exercise balls.

8. 1-bedroom hotel suites in Scarborough with essentially stocked kitchens.

1-bedroom hotel suites in Scarborough with essentially stocked kitchens.
South Portland
9.0 out of 10, Wonderful, (10 reviews)
"We really appreciated our stay!"
United States
Anonymous traveller
The price is HK$1,126
HK$1,407 total
includes taxes & fees
1 Sept - 2 Sept
1-bedroom hotel suites in Scarborough with essentially stocked kitchens.
A modern house with a wooden exterior, a small garden, and a visible window.

9. Spacious and Contemporary Condo in the Heart of Portland - Close to Beach

Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
East Bayside
8.8 out of 10, Excellent, (39 reviews)
"Overall a pleasing stay."
United States
Mallory D.
The price is HK$1,095
HK$3,705 total
includes taxes & fees
31 Aug - 1 Sept
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
A modern kitchen with a dining area, featuring a round table, chairs, and a hanging light fixture.

10. Elegant condo - walk to Portland's best restaurants & Old Port

Elegant condo - walk to Portland's best restaurants & Old Port
East Bayside
9.4 out of 10, Exceptional, (83 reviews)
"It was nice if you like being right in town. There is no view and it's a bit noisy."
United States
Nancy S.
The price is HK$1,317
HK$4,022 total
includes taxes & fees
25 Aug - 26 Aug
Elegant condo - walk to Portland's best restaurants & Old Port
A room with a white table, a chair, a colorful rug, and a ceiling fan.

11. Walkable near downtown 1 Bedroom

Walkable near downtown 1 Bedroom
West Bayside
5.2 out of 10, (5 reviews)
"Stay was ok! Not worth the listing price. Does the trick if you need a quick place to stay. Other than two mugs, very few supplies. "
United States
Thomas H.
The price is HK$823
HK$1,412 total
includes taxes & fees
1 Sept - 2 Sept
Walkable near downtown 1 Bedroom
A modern living room with a wooden dining table, a sofa, and a coffee table.

12. Furnished 1BR/1BA Walk to Maine Med/Mercy. Parking & All utilities included!

Furnished 1BR/1BA Walk to Maine Med/Mercy. Parking & All utilities included!
West End
9.6 out of 10, Exceptional, (8 reviews)
"Great place to stay - lovely building and really nicely kept, and it’s a perfect location if you want to walk down to Old Port, about 20 minutes. Would love to come back!"
United States
Cate
The price is HK$1,524
HK$3,755 total
includes taxes & fees
6 Sept - 7 Sept
Furnished 1BR/1BA Walk to Maine Med/Mercy. Parking & All utilities included!
A modern kitchen with a large island, dining chairs, and a view of the cityscape through large windows.

13. Walk to Back Cove | Smart TV | Wi-Fi | Parking

Walk to Back Cove | Smart TV | Wi-Fi | Parking
Oakdale
8.0 out of 10, Very good, (2 reviews)
"A lovely place."
United States
Susan S.
The price is HK$949
HK$3,427 total
includes taxes & fees
25 Aug - 26 Aug
Walk to Back Cove | Smart TV | Wi-Fi | Parking
A kitchen with wooden cabinets, a stainless steel dishwasher, a coffee maker, and a potted plant.

14. Cozy Two Bedroom on Munjoy Hill

Cozy Two Bedroom on Munjoy Hill
Munjoy Hill
The price is HK$1,271
HK$2,556 total
includes taxes & fees
1 Sept - 2 Sept
Cozy Two Bedroom on Munjoy Hill
A cozy living room with a grey sofa, a wooden coffee table with a charcuterie board, and two glasses of white wine on a side table.

15. 2BR Apt | Full Kitchen | 10 Min to Old Port

2BR Apt | Full Kitchen | 10 Min to Old Port
Oakdale
10.0 out of 10, Exceptional, (2 reviews)
"It was so easy booking this apartment. They were so helpful and quick to answer my questions. They took great care of us during our stay & were so attentive! It was very warm in the apartment when we first arrived. I told them about it & maintenance immediately arrived with a small window unit for the bedroom. It cooled things down tremendously.The apartment was clean and the linens were laid out on the bed. Turn key as we walked inside.I am definitely going to rent from this company...
United States
Tracy H.
The price is HK$1,105
HK$3,290 total
includes taxes & fees
20 Sept - 21 Sept
2BR Apt | Full Kitchen | 10 Min to Old Port
A theater with a marquee reading "STATE" and a classic architectural design.

16. 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 HK$1,919
HK$3,323 total
includes taxes & fees
9 Sept - 10 Sept
Luxury Condo Downtown Portland Old Port
A loft-style room with a sofa, a small table, a skylight, and a kitchenette.

17. Great suburban location close to town!

Great suburban location close to town!
Deering Center
The price is HK$1,333
HK$1,998 total
includes taxes & fees
4 Sept - 5 Sept
Great suburban location close to town!
A kitchen with a wooden countertop, a black kettle, a vase with flowers, and a small wire basket.

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

Charming Studio apartment with WiFi, AC in welcoming Portland
Munjoy Hill
9.4 out of 10, Exceptional, (25 reviews)
"Great place! We would definitely return if we were in the area."
United States
Preston
Charming Studio apartment with WiFi, AC in welcoming Portland
A multi-story building with a stone facade, large windows, and a corner entrance.

19. Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (10 reviews)
"Truly a wonderful place with an unbeatable location. Highly recommend for a visit to Portland."
United States
Eric
The price is HK$4,275
HK$5,836 total
includes taxes & fees
31 Aug - 1 Sept
Evalina Hotel
A living room with a sofa, armchairs, a coffee table, and a potted plant.

20. Beautiful 1st Floor Apartment & Amazing Shower

Beautiful 1st Floor Apartment & Amazing Shower
Parkside
9.2 out of 10, Wonderful, (29 reviews)
"This was a clean and good location for our stay. "
United States
Jocelyn R.
The price is HK$1,759
HK$2,704 total
includes taxes & fees
30 Aug - 31 Aug
Beautiful 1st Floor Apartment & Amazing Shower
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 Portland Hotel Reviews

Portland Harbor Hotel

Portland Harbor Hotel

10/10 Excellent
"Location of the hotel is one block from the Old Port with numerous stores and restaurants. Hotel has its own parking garage with unlimited access. Parking fee for hotel guests is $45 per day."
john 3-night trip
Posted 10 hours ago
Portland Harbor Hotel

Find out more about Portland

Search for holiday rentals in Portland on Expedia! You can easily find your home rentals, villas, holiday apartments in Portland using one of the methods below:

  • View our selection of featured holiday rentals in Portland
  • Use the map to find apartments and other holiday homes in the Portland neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Portland while they last

Look no further and take a look at our great range of rental properties in Portland!

Frequently asked questions

Can I find a holiday rental in Portland?

Yes, there are holiday rentals in Portland close to Maine Narrow Gauge Railroad, or you can select a more secluded option if you're looking for a relaxing stay. Tourists who visit Portland speak highly of the bustling port and array of shops. The entertainment choices and great live music are some other things you might like to check out during your trip.

What are some of the best holiday rentals that Portland has to offer?

Cozy&Quiet Home in Portland ME. One Bedroom with dedicated Bathroom “No Kitchen”: This highly rated holiday home rental in Portland is located on the beach, and offers a fireplace, air conditioning and a Smart TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave and kitchenware. Our travellers also rate Backyard Paradise as a favourite home for rent in Portland.

How many holiday rentals are there in Portland?

Choose from 89 Expedia holiday rentals in Portland for a memorable holiday.

What can I see and do in Portland?

Maine Narrow Gauge Railroad and Bayside Bowl are a couple of the family-friendly sights, whereas cultural attractions include Merrill Auditorium and Portland Museum of Art. While here, Casco Bay Lines Ferry Terminal and Cross Insurance Arena are other places worth a visit.

What are holiday rentals like in Portland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Portland. Holiday rentals provide amenities like kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from shared hotel lifts and busy front desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great choice for small groups.