Portland Holiday Rentals

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Our top choices for Portland holiday rentals

Peaceful & minutes from the Old Port with private parking

Peaceful & minutes from the Old Port with private parking
Knightville
9.8 out of 10, Exceptional, (7 reviews)
"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$322
includes taxes & fees
15 Feb - 16 Feb
Peaceful & minutes from the Old Port with private parking

Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
9.8 out of 10, Exceptional, (25 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$328
includes taxes & fees
22 Feb - 23 Feb
Sunny Spot with Private Parking.

Port City Nest: Beautiful 2bd w/ Balcony & Parking

Port City Nest: Beautiful 2bd w/ Balcony & Parking
Parkside
10.0 out of 10, Exceptional, (2 reviews)
"Very nice apartment. Had everything we needed. "
United States
Bob S.
The price is NZ$401
includes taxes & fees
19 Feb - 20 Feb
Port City Nest: Beautiful 2bd w/ Balcony & Parking

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, (11 reviews)
"A great location and a comfortable place to stay!"
United States
Andrew K.
The price is NZ$355
includes taxes & fees
16 Feb - 17 Feb
Charming Studio apartment with WiFi, AC in welcoming Portland

Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (129 reviews)
"Tidy place in a great location! "
United States
Mary M.
The price is NZ$334
includes taxes & fees
8 Mar - 9 Mar
Adorable Portland getaway on the Eastern Promenade

The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (92 reviews)
"Loved this place and would definitely stay here next time we go back."
United States
Eleni
The price is NZ$290
includes taxes & fees
22 Feb - 23 Feb
The Weldon Hotel

Charming West End Hideaway. Private Parking

Charming West End Hideaway. Private Parking
West End
10.0 out of 10, Exceptional, (47 reviews)
"Excellent place in every way-- I wish we could have stayed longer!"
United States
Alicia
The price is NZ$340
includes taxes & fees
16 Feb - 17 Feb
Charming West End Hideaway. Private Parking

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

Cozy 1-bedroom apartment in awesome Portland with WiFi, AC
Parkside
8.0 out of 10, Very good, (4 reviews)
"Everything was perfect."
United States
Edward J.
The price is NZ$245
includes taxes & fees
26 Feb - 27 Feb
Cozy 1-bedroom apartment in awesome Portland with WiFi, AC

City Amenities, Casco Bay Sunrises and Natural Beauty

City Amenities, Casco Bay Sunrises and Natural Beauty
East Deering
9.8 out of 10, Exceptional, (124 reviews)
"Great location for an our trip; laundry in basement "
United States
maria h.
The price is NZ$464
includes taxes & fees
19 Feb - 20 Feb
City Amenities, Casco Bay Sunrises and Natural Beauty

Beautiful 1st Floor Apartment & Amazing Shower

Beautiful 1st Floor Apartment & Amazing Shower
Parkside
9.0 out of 10, Wonderful, (27 reviews)
"This was a clean and good location for our stay. "
United States
Jocelyn R.
The price is NZ$243
includes taxes & fees
15 Feb - 16 Feb
Beautiful 1st Floor Apartment & Amazing Shower

Skyline 138: Charming West End Mansard Penthouse

Skyline 138: Charming West End Mansard Penthouse
Parkside
9.2 out of 10, Wonderful, (25 reviews)
"Nice easy process, clean place, cute decor, easy to walk and uber to hot spots we wanted to see"
United States
Faith E.
The price is NZ$516
includes taxes & fees
16 Feb - 17 Feb
Skyline 138: Charming West End Mansard Penthouse

1200 Sq Ft ♦ West End Gem ♦ Perfect Location

1200 Sq Ft ♦ West End Gem ♦ Perfect Location
West End
9.4 out of 10, Exceptional, (98 reviews)
"Great location with easy parking"
United States
Lauren J.
1200 Sq Ft ♦ West End Gem ♦ Perfect Location

Cozy, Elegant and Bright 2 bed in the East End

Cozy, Elegant and Bright 2 bed in the East End
Munjoy Hill
9.8 out of 10, Exceptional, (52 reviews)
"Great location and cozy."
United States
Heather G.
The price is NZ$554
includes taxes & fees
16 Feb - 17 Feb
Cozy, Elegant and Bright 2 bed in the East End

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, (58 reviews)
"Quiet, close to everything and east to find."
United States
Jesse M.
The price is NZ$499
includes taxes & fees
15 Feb - 16 Feb
1200 sq ft ♦ West End Townhouse ♦ Perfect Location

Bright & Spacious Apartment with Amazing Shower

Bright & Spacious Apartment with Amazing Shower
Parkside
8.4 out of 10, Very good, (18 reviews)
"Super cute. Enjoyed our stay"
United States
Amber T.
The price is NZ$243
includes taxes & fees
15 Feb - 16 Feb
Bright & Spacious Apartment with Amazing Shower

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
9.4 out of 10, Exceptional, (3 reviews)
"All was great...clean and convenient."
United States
Krista P.
The price is NZ$762
includes taxes & fees
16 Feb - 17 Feb
Furnished 1BR/1BA Walk to Maine Med/Mercy. Parking & All utilities included!

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, (76 reviews)
"Property is clean quiet."
United States
Spencer S.
The price is NZ$823
includes taxes & fees
20 Feb - 21 Feb
Elegant condo - walk to Portland's best restaurants & Old Port

Modern & Sunny House Steps from the Promenade. Private Parking!

Modern & Sunny House Steps from the Promenade. Private Parking!
Munjoy Hill
10.0 out of 10, Exceptional, (38 reviews)
"Perfect stay for a quick trip to Portland! "
United States
stacey p.
The price is NZ$597
includes taxes & fees
17 Feb - 18 Feb
Modern & Sunny House Steps from the Promenade. Private Parking!

State of Charm | Historic West End Haven

State of Charm | Historic West End Haven
Parkside
8.8 out of 10, Excellent, (9 reviews)
"We had a wonderful time, loved the home, relaxed and enjoyed the sights of Portland! "
United States
Nancy H.
The price is NZ$605
includes taxes & fees
25 Feb - 26 Feb
State of Charm | Historic West End Haven

Walk to Old Port ♦ West End Condo ♦ Parking

Walk to Old Port ♦ West End Condo ♦ Parking
West End
9.6 out of 10, Exceptional, (80 reviews)
"Great location and very spacious! Easy commutation - must stay! "
United States
Courtney H.
The price is NZ$450
includes taxes & fees
16 Feb - 17 Feb
Walk to Old Port ♦ West End Condo ♦ 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$258 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 Portland Observatory, 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 acclaimed theatre scene and fascinating museums 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.

How many holiday rentals are there in Portland?

Choose from 84 Expedia holiday rentals in Portland for a memorable holiday.

What can I see and do in Portland?

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