Portland Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Portland

Sunny Spot with Private Parking.

2.0 star property
Knightville
9.8 out of 10, Exceptional, (24)
"Had a great stay here! The place was very clean and well-equipped. Convenient parking and a short drive to Portland center. Would stay here again!"
United States
Emre G.
The price is NZ$315
includes taxes & fees
16 Nov - 17 Nov
Sunny Spot with Private Parking.

Beautiful 1st Floor Apartment & Amazing Shower

Parkside
9.0 out of 10, Wonderful, (26)
"My brother in law and I stayed here while my husband was hospitalized at the Maine Med and it was a lovely property. Everything was clean and organized, check in was easy and the hosts were responsive and kind. I would stay here again!"
United States
Lillian L.
The price is NZ$277
includes taxes & fees
18 Nov - 19 Nov
Beautiful 1st Floor Apartment & Amazing Shower

Studio Apartment near downtown Walkable!

West Bayside
7.6 out of 10, Good, (5)
"The apartment was exactly as advertised: relatively spacious because of all the clear space, with everything needed for someone on a brief visit. The person who rents the apartment went out of his way to be helpful when I contacted him. "
United States
Helaine
The price is NZ$246
includes taxes & fees
17 Nov - 18 Nov
Studio Apartment near downtown Walkable!

Peaceful & minutes from the Old Port with private parking

Knightville
9.8 out of 10, Exceptional, (7)
"My husband and I had a wonderful weekend in South Portland and enjoyed the central location and charming touches of Jennifer’s apartment. The space is lovely, exactly as described in the listing. The communication was clear and detailed. We will definitely return!"
United States
Caitlin C.
The price is NZ$344
includes taxes & fees
16 Nov - 17 Nov
Peaceful & minutes from the Old Port with private parking

Adorable Portland getaway on the Eastern Promenade

Munjoy Hill
9.6 out of 10, Exceptional, (125)
"Welcoming small apartment in a beautiful Portland neighborhood. Clean and stocked with everything we needed. Very helpful hosts. "
United States
Annalise M.
The price is NZ$332
includes taxes & fees
7 Dec - 8 Dec
Adorable Portland getaway on the Eastern Promenade

The Weldon Hotel

4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (86)
"Absolutely beautiful place to stay. "
United States
James
The price is NZ$486
includes taxes & fees
7 Dec - 8 Dec
The Weldon Hotel

Cozy 1-bedroom apartment in awesome Portland with WiFi, AC

Parkside
8.0 out of 10, Very good, (4)
"Everything was perfect."
United States
Edward J.
The price is NZ$261
includes taxes & fees
16 Nov - 17 Nov
Cozy 1-bedroom apartment in awesome Portland with WiFi, AC

Luxury on Back Cove - Three Gables

Rosemont
10.0 out of 10, Exceptional, (8)
"GoodLocation, very clean. Would stay again "
United States
Carly B.
The price is NZ$644
includes taxes & fees
16 Nov - 17 Nov
Luxury on Back Cove - Three Gables

In-town no frills 2 bedroom apt

West Bayside
8.4 out of 10, Very good, (14)
"Beds were very comfortable. Parking was a little difficult. 3rd floor was a little tough on my 83 year old mother. But it was clean and roomy and close to downtown shopping and touristy attractions."
United States
Betsy Jean
The price is NZ$265
includes taxes & fees
20 Nov - 21 Nov
In-town no frills 2 bedroom apt

West End Bright Spot with Parking.

West End
10.0 out of 10, Exceptional, (16)
"This place was so so cute! We are really thankful for Jennifer’s responsiveness and hospitality. And the location was pristine. Would definitely stay again."
United States
Brant H.
The price is NZ$366
includes taxes & fees
16 Nov - 17 Nov
West End Bright Spot with Parking.

Bright & Spacious Apartment with Amazing Shower

Parkside
8.4 out of 10, Very good, (16)
"Great location. Great price. Soft beds. Super Dirty bathroom door which was a bit of a miss. Otherwise, we would stay there again!"
United States
Liz T.
The price is NZ$278
includes taxes & fees
16 Nov - 17 Nov
Bright & Spacious Apartment with Amazing Shower

Charming Studio apartment with WiFi, AC in welcoming Portland

Munjoy Hill
9.6 out of 10, Exceptional, (11)
"This was a great stay through and through. Excellent condition, very responsive before and during the stay, and a great location. 10/10 will recommend to anyone staying in Portland! "
United States
Kirsten
The price is NZ$401
includes taxes & fees
16 Nov - 17 Nov
Charming Studio apartment with WiFi, AC in welcoming Portland

1200 Sq Ft ♦ West End Gem ♦ Perfect Location

West End
9.4 out of 10, Exceptional, (96)
"This location is convenient to places to visit in Portland and major highways to go costal. Very clean and cozy. Would stay again."
United States
Nancy M.
The price is NZ$467
includes taxes & fees
16 Nov - 17 Nov
1200 Sq Ft ♦ West End Gem ♦ Perfect Location

Charming West End Hideaway. Private Parking

West End
10.0 out of 10, Exceptional, (46)
"Great apartment in an excellent location. Super walkable to most of Portland. We loved the charming decor and outdoor deck! Furnishings and fixtures were a bit dated and we encountered a few issues with bugs getting in, likely because of the window AC unit. Location felt very safe and hosts were kind."
United States
Ansley D.
The price is NZ$367
includes taxes & fees
16 Nov - 17 Nov
Charming West End Hideaway. Private Parking

Arlie`s Digs! - One Block To Willard Beach!

Willard Beach
10.0 out of 10, Exceptional, (60)
"Near beach, walking, bakery, ice cream and close to great restaurants. Lovely spot and easily accommodated 2 couples. Would stay here again!"
United States
Kirstin D.
The price is NZ$611
includes taxes & fees
2 Dec - 3 Dec
Arlie`s Digs! - One Block To Willard Beach!

Glorious getaway on Portland's Eastern Promenade.

Munjoy Hill
9.8 out of 10, Exceptional, (170)
"Lots of room, great neighborhood, easy entry"
United States
Joel F.
The price is NZ$441
includes taxes & fees
16 Nov - 17 Nov
Glorious getaway on Portland's Eastern Promenade.

Large 1 bed w/ private deck

Deering Center
6.0 out of 10, (2)
"Clean, comfortable bed, and a good location. Kitchen items and towels were very minimal. No extras! Also, bedroom is on the second floor and the one bathroom is on the first. "
United States
Mary P.
The price is NZ$257
includes taxes & fees
16 Nov - 17 Nov
Large 1 bed w/ private deck

Back Cove Gem ★ 5 Min to Old Port ★ Bright and New

Oakdale
10.0 out of 10, Exceptional, (43)
"Perfect accommodations! My best friend and I, along with my husband, had the best time. The beds were dreamy and the kitchen had all the supplies we needed. Quiet neighborhood within a 5 minute Uber to downtown- our first trip to Portland and we hope to be back soon!"
United States
Tara (Harris) K.
The price is NZ$552
includes taxes & fees
16 Nov - 17 Nov
Back Cove Gem ★ 5 Min to Old Port ★ Bright and New

Beautiful West End Apartment

West End
8.0 out of 10, Very good, (3)
"Unfortunately, the pictures look much better than the actual property. This could be a cute space but it is not at all kept up. All of the furniture is old, scratched and just thrown together. We felt like things were thrown together like a frat house. Paint was chipped and scratched all through the house, colors didn't match and there was thick dust on blinds and molding. Many of the blinds, shutters and lighting were partially broken. There was no effort to make it comfy or keep it...
United States
Jody O.
The price is NZ$498
includes taxes & fees
17 Nov - 18 Nov
Beautiful West End Apartment

Roof Deck - Parking - 5 Min Downtown

2.0 star property
Oakdale
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
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.
Save an average of 15% on thousands of hotels when you're signed in

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$246 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 fascinating museums and acclaimed theatre scene 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?

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach: This holiday home rental outside of Portland is located on the beach, and has a patio, a garden and a BBQ to put you at ease 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. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Portland?

Choose from 87 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 Bayside Bowl are a couple of the family-friendly sights, whereas cultural attractions include Merrill Auditorium and Wadsworth-Longfellow House. 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.