Portland Holiday Rentals

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Our top choices for Portland holiday rentals

Apartment in Knightville

Sunny Spot with Private Parking.
2.0 star property
9.8 out of 10, Exceptional, (25)
"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$347
includes taxes & fees
6 Jan - 7 Jan 2026
Sunny Spot with Private Parking.
9.6 out of 10, Exceptional, (128)
"The place was perfect. It was right in the middle of everything and a perfe spot for a getaway"
United States
Jon S.
The price is NZ$340
includes taxes & fees
2 Jan - 3 Jan 2026
Adorable Portland getaway on the Eastern Promenade

Aparthotel in Downtown Portland

The Weldon Hotel
4.5 star property
9.8 out of 10, Exceptional, (90)
"Loved this place and would definitely stay here next time we go back."
United States
Eleni
The price is NZ$466
includes taxes & fees
16 Jan - 17 Jan 2026
The Weldon Hotel
10.0 out of 10, Exceptional, (1)
"Loved staying at your Nest! All was great but maybe a couple of cozy blanks in living room for lounging? Thanks again-Ruth"
United States
Ruth R.
The price is NZ$403
includes taxes & fees
4 Jan - 5 Jan 2026
Port City Nest: Beautiful 2bd w/ Balcony & Parking
9.6 out of 10, Exceptional, (11)
"A great location and a comfortable place to stay!"
United States
Andrew K.
The price is NZ$366
includes taxes & fees
1 Jan - 2 Jan 2026
Charming Studio apartment with WiFi, AC in welcoming Portland
10.0 out of 10, Exceptional, (47)
"Excellent place in every way-- I wish we could have stayed longer!"
United States
Alicia
The price is NZ$392
includes taxes & fees
11 Jan - 12 Jan 2026
Charming West End Hideaway. Private Parking

Apartment in West Bayside

In-town no frills 2 bedroom apt
8.6 out of 10, Excellent, (17)
"Good place to stay in. Safe. However, it would be good to know about the steep and narrow spiral staircase, in case you have lots of heavy luggage."
United States
Omar S.
The price is NZ$268
includes taxes & fees
1 Jan - 2 Jan 2026
In-town no frills 2 bedroom apt
9.8 out of 10, Exceptional, (52)
"Great location and cozy."
United States
Heather G.
The price is NZ$397
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy, Elegant and Bright 2 bed in the East End
9.8 out of 10, Exceptional, (7)
"This well- appointed apartment was perfect for our stay in the Portland area. Jennifer was always quick to answer any questions. We would definitely recommend this listing."
United States
Lynn E.
The price is NZ$366
includes taxes & fees
4 Jan - 5 Jan 2026
Peaceful & minutes from the Old Port with private parking
9.0 out of 10, Wonderful, (26)
"This was a clean and good location for our stay. "
United States
Jocelyn R.
The price is NZ$273
includes taxes & fees
7 Jan - 8 Jan 2026
Beautiful 1st Floor Apartment & Amazing Shower
9.8 out of 10, Exceptional, (32)
"Clean, great location, excellent communication with host, perfectly furnished for our group"
United States
Elizabeth P.
East end. Walk to food, beer and downtown fun.
10.0 out of 10, Exceptional, (4)
"Great place, so close to everything and a clean, quiet spot to sleep."
United States
Dan K.
The price is NZ$651
includes taxes & fees
1 Jan - 2 Jan 2026
THE RALEIGH BnB APARTMENT SELF CHECK-IN / Free Off-Street Parking
10.0 out of 10, Exceptional, (63)
"We had a wonderful week here. Fantastic proximity to the beach & a great bakery and ice cream shop. They accommodated us and our dog very well and had everything we need for a great stay. "
United States
Elizabeth C.
The price is NZ$599
includes taxes & fees
4 Jan - 5 Jan 2026
Arlie`s Digs! - One Block To Willard Beach!
9.8 out of 10, Exceptional, (122)
"Perfect location and the host was immediately repsonsive and always friendly!"
United States
Jon L.
The price is NZ$516
includes taxes & fees
4 Jan - 5 Jan 2026
City Amenities, Casco Bay Sunrises and Natural Beauty
9.4 out of 10, Exceptional, (98)
"Great location with easy parking"
United States
Lauren J.
The price is NZ$448
includes taxes & fees
8 Jan - 9 Jan 2026
1200 Sq Ft ♦ West End Gem ♦ Perfect Location
2.0 star property
10.0 out of 10, Exceptional, (3)
"Excellent stay! 3rd floor unit so walk up the stairs is needed. The space was beautifully decorated, and the hosts even had flowers waiting upon arrival. Very cozy with the fireplace and huge outdoor patio. Would love to stay again!"
United States
Ilyna W.
Roof Deck | Parking | 5 Min Downtown
9.8 out of 10, Exceptional, (171)
"Great location, very clean, everything we needed!"
United States
dawn m.
The price is NZ$433
includes taxes & fees
1 Jan - 2 Jan 2026
Glorious getaway on Portland's Eastern Promenade.
10.0 out of 10, Exceptional, (38)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
The price is NZ$629
includes taxes & fees
4 Jan - 5 Jan 2026
Modern & Sunny House Steps from the Promenade. Private Parking!
9.6 out of 10, Exceptional, (10)
"We had a great time at this beautiful condo. The location was perfect, the home was dog friendly and there was parking included. Will definitely stay there again! "
United States
Julia C.
The price is NZ$643
includes taxes & fees
5 Jan - 6 Jan 2026
Local Landmark! Gorgeous Historic Home
2.0 star property
10.0 out of 10, Exceptional, (2)
"Absolutely fantastic stay! The house is clean, comfortable and has all the amenities to stay in. However with such a great location to all that Portland has to offer taking a quick walk to whatever strikes your fancy is highly recommended. The bakery on the corner has great coffee and baked goods. We didn’t need much from Doug but when I messaged him he was very responsive and accommodating. The beds are extremely comfortably. The location is quiet, within walking distance or a quick uber...
United States
Carl K.
The price is NZ$687
includes taxes & fees
18 Jan - 19 Jan 2026
Chic 3-bedroom house in Munjoy Hill with off-street parking.
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$232 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 Company and Museum, 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 great live music and entertainment choices 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?

Beautiful, single story ranch. Next to city park with ocean view!: This highly rated holiday home rental in Portland offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of garden in this rental home to help you unwind. Our travellers also rate Back yard paradise as a favourite home for rent in Portland.

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 Company and Museum and Children's Museum and Theatre of Maine are a couple of the family-friendly sights, whereas cultural attractions include Merrill Auditorium and Portland Museum of Art. While here, Fore Street Gallery and Casco Bay Lines Ferry Terminal 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.