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Portland Holiday Rentals

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Our top choices for Portland holiday rentals

1. Studio Apartment near downtown Walkable!

Studio Apartment near downtown Walkable!
West Bayside
8.2 out of 10, Very good, (14 reviews)
"A perfectly decent place to stay, plenty of restaurants and bars within reasonable walking distance. Neighborhood is a bit rough, as the listing mentioned, but no problems while I was there. Response time on questions to the host could be better."
Canada
Brian
The price is NZ$300
includes taxes & fees
18 Aug - 19 Aug
Studio Apartment near downtown Walkable!

2. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (110 reviews)
"Really nice room and location"
United States
Victoria
The price is NZ$661
includes taxes & fees
1 Sept - 2 Sept
The Weldon Hotel

3. 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 NZ$291
includes taxes & fees
16 Aug - 17 Aug
Walkable near downtown 1 Bedroom

4. 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 NZ$444
includes taxes & fees
31 Aug - 1 Sept
1200 Sq Ft ♦ West End Gem ♦ Perfect Location

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, (88 reviews)
"Host was very responsive, and helpful. Location is amazing for walking the city."
United States
Chris P.
Walk to Old Port ♦ West End Condo ♦ Parking

6. 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."
United States
Rob M.
The price is NZ$710
includes taxes & fees
3 Sept - 4 Sept
1200 sq ft ♦ West End Townhouse ♦ Perfect Location

7. 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, (38 reviews)
"Overall a pleasing stay."
United States
Mallory D.
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach

8. Private Entrance Residential Portland

Private Entrance Residential Portland
Deering Center
8.6 out of 10, Excellent, (8 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 NZ$224
includes taxes & fees
2 Sept - 3 Sept
Private Entrance Residential Portland

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

Historic Home in the West End. Private Parking.
West End
10.0 out of 10, Exceptional, (59 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 NZ$629
includes taxes & fees
7 Sept - 8 Sept
Historic Home in the West End. Private Parking.

10. 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, (9 reviews)
"We really appreciated our stay!"
United States
Anonymous traveller
The price is NZ$318
includes taxes & fees
14 Sept - 15 Sept
1-bedroom hotel suites in Scarborough with essentially stocked kitchens.

11. 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, (7 reviews)
"All was great...clean and convenient."
United States
Krista P.
Furnished 1BR/1BA Walk to Maine Med/Mercy. Parking & All utilities included!

12. 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$723
includes taxes & fees
9 Sept - 10 Sept
Luxury Condo Downtown Portland Old Port

13. 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 NZ$701
includes taxes & fees
17 Aug - 18 Aug
2BR Apt | Full Kitchen | 10 Min to Old Port

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

Elegant condo - walk to Portland's best restaurants & Old Port
East Bayside
9.2 out of 10, Wonderful, (82 reviews)
"I had a wonderful week at this perfect place. Met my expectations and way more. So walkable all over Portland. I will be back. Thank you so very much."
United States
Margaret H.
The price is NZ$852
includes taxes & fees
25 Aug - 26 Aug
Elegant condo - walk to Portland's best restaurants & Old Port

15. Great suburban location close to town!

Great suburban location close to town!
Deering Center
The price is NZ$300
includes taxes & fees
18 Aug - 19 Aug
Great suburban location close to town!

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, (24 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

17. Beautiful 1st Floor Apartment & Amazing Shower

Beautiful 1st Floor Apartment & Amazing Shower
Parkside
9.2 out of 10, Wonderful, (29 reviews)
"Apartment was as described. Clean, walking distort downtown and parks. Enjoyed stay. Easy communication with host. "
United States
James R.
The price is NZ$542
includes taxes & fees
17 Aug - 18 Aug
Beautiful 1st Floor Apartment & Amazing Shower

18. Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (9 reviews)
"Truly a wonderful place with an unbeatable location. Highly recommend for a visit to Portland."
United States
Eric
The price is NZ$1,213
includes taxes & fees
31 Aug - 1 Sept
Evalina Hotel

19. Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
10.0 out of 10, Exceptional, (31 reviews)
"Cute property.. also really suitable for long stay as the amenities were complete and near groceries and some restaurants and cafes.. convenient!"
United States
Giana
The price is NZ$542
includes taxes & fees
10 Sept - 11 Sept
Sunny Spot with Private Parking.

20. Willard Beach–Apartment Near Portland & Parks

Willard Beach–Apartment Near Portland & Parks
Willard Beach
10.0 out of 10, Exceptional, (5 reviews)
"Excellent in every way."
United States
Robert B.
The price is NZ$613
includes taxes & fees
16 Aug - 17 Aug
Willard Beach–Apartment Near Portland & Parks
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

Find out more about Portland

Everything you need to know about Portland 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 Portland 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 Portland holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Portland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Portland. 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 Portland 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 Portland holiday rentals we have selected for you start as low as NZ$300 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Portland rentals

At Expedia, we put the best Portland 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 Portland 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 Portland 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 Portland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.

How many holiday rentals are there in Portland?

Choose from 88 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.