Portland Holiday Rentals

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Check prices for these dates

In two weeks
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sept - 27 Sept

Our top choices for Portland holiday rentals

1 bedroom, WiFi, bed sheets

Studio Apartment near downtown Walkable!

Studio Apartment near downtown Walkable!
West Bayside
8.4 out of 10, Very good, (7 reviews)
"Maine Oyster Company was a highlight of the trip! "
United Kingdom
Tyler P.
The price is HK$823
HK$1,403 total
includes taxes & fees
14 Jun - 15 Jun
Studio Apartment near downtown Walkable!
Smart TV

Willard Beach–Private Apt Near Portland & Parks

Willard Beach–Private Apt Near Portland & Parks
Willard Beach
10.0 out of 10, Exceptional, (5 reviews)
"Excellent in every way."
United States
Robert B.
The price is HK$1,051
HK$2,291 total
includes taxes & fees
8 Jun - 9 Jun
Willard Beach–Private Apt Near Portland & Parks
Property grounds

South Portland Beach area rental

South Portland Beach area rental
Willard Beach
10.0 out of 10, Exceptional, (1 review)
"Great place, just like pictures "
United States
Evan M.
The price is HK$1,515
HK$2,813 total
includes taxes & fees
9 Jun - 10 Jun
South Portland Beach area rental
Interior

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, (59 reviews)
"Nice place. Good location."
United States
Rob M.
The price is HK$726
HK$2,850 total
includes taxes & fees
7 Jun - 8 Jun
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
TV

Private Entrance Residential Portland

Private Entrance Residential Portland
Deering Center
8.8 out of 10, Excellent, (6 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$741
HK$1,312 total
includes taxes & fees
8 Jun - 9 Jun
Private Entrance Residential Portland
Interior

Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
9.8 out of 10, Exceptional, (26 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 HK$1,387
HK$2,366 total
includes taxes & fees
9 Jun - 10 Jun
Sunny Spot with Private Parking.
Interior

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$741
HK$1,312 total
includes taxes & fees
4 Jun - 5 Jun
Walkable near downtown 1 Bedroom
Interior

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, (12 reviews)
"A great location and a comfortable place to stay!"
United States
Andrew K.
The price is HK$1,183
HK$2,033 total
includes taxes & fees
18 Jun - 19 Jun
Charming Studio apartment with WiFi, AC in welcoming Portland
Exterior detail

Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (132 reviews)
"The host was very friendly and it was an easy apartment to check into. "
United States
Kendall M.
The price is HK$1,544
HK$2,426 total
includes taxes & fees
11 Jun - 12 Jun
Adorable Portland getaway on the Eastern Promenade
Fitness facility

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

1-bedroom hotel suites in Scarborough with essentially stocked kitchens.
South Portland
10.0 out of 10, Exceptional, (1 review)
"We really appreciated our stay!"
United States
Anonymous traveller
The price is HK$1,716
HK$2,144 total
includes taxes & fees
1 Jul - 2 Jul
1-bedroom hotel suites in Scarborough with essentially stocked kitchens.
Outdoor dining

Peaceful & minutes from the Old Port with private parking

Peaceful & minutes from the Old Port with private parking
Knightville
9.6 out of 10, Exceptional, (10 reviews)
"Great little place in south Portland! Close to many parks, lighthouses, and driving distance to downtown. Parking downtown and in the old port area can be tricky and expensive though. "
United States
Christopher R.
The price is HK$1,513
HK$2,597 total
includes taxes & fees
7 Jun - 8 Jun
Peaceful & minutes from the Old Port with private parking
Smart TV

Hidden private one bedroom gem

Hidden private one bedroom gem
Oakdale
7.0 out of 10, Good, (2 reviews)
"This is a great little place to stay for one or two people. It was perfect for us and our small dog. The room was easy to find. The host provided excellent instructions. The place was clean. It was also easy to explore the rest of Portland from here. I liked being able to park on a quiet street as opposed to dealing with city parking. I would stay here again."
United States
Lisa B.
The price is HK$1,354
HK$2,518 total
includes taxes & fees
5 Jun - 6 Jun
Hidden private one bedroom gem
Exterior detail

1200 Sq Ft ♦ West End Gem ♦ Perfect Location

1200 Sq Ft ♦ West End Gem ♦ Perfect Location
West End
9.4 out of 10, Exceptional, (101 reviews)
"Screen door was broke, would not close properly. Inside was very clean and comfortable beds. We just slept there and is fine for 2 people but not more. "
United States
Carolyn S.
The price is HK$815
HK$2,041 total
includes taxes & fees
4 Jun - 5 Jun
1200 Sq Ft ♦ West End Gem ♦ Perfect Location
Interior

East end. Walk to food, beer and downtown fun.

East end. Walk to food, beer and downtown fun.
Munjoy Hill
9.8 out of 10, Exceptional, (35 reviews)
"Clean, great location, excellent communication with host, perfectly furnished for our group"
United States
Elizabeth P.
The price is HK$1,662
HK$2,909 total
includes taxes & fees
14 Jun - 15 Jun
East end. Walk to food, beer and downtown fun.
Smart TV

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$853
HK$1,605 total
includes taxes & fees
4 Jun - 5 Jun
Beautiful 1st Floor Apartment & Amazing Shower
Beach

THE RALEIGH BnB APARTMENT SELF CHECK-IN / Free Off-Street Parking

THE RALEIGH BnB APARTMENT SELF CHECK-IN / Free Off-Street Parking
Munjoy Hill
10.0 out of 10, Exceptional, (4 reviews)
"Great place, so close to everything and a clean, quiet spot to sleep."
United States
Dan K.
The price is HK$1,959
HK$3,861 total
includes taxes & fees
4 Jun - 5 Jun
THE RALEIGH BnB APARTMENT SELF CHECK-IN / Free Off-Street Parking
TV

The Coastal Connection

The Coastal Connection
Thorton Heights
9.0 out of 10, Wonderful, (2 reviews)
"Very convenient, comfortable, and bright apartment. We appreciated that dogs were allowed as well."
United States
Sheryl S.
The price is HK$1,862
HK$3,789 total
includes taxes & fees
16 Jun - 17 Jun
The Coastal Connection
Flat-screen TV, Netflix, books, streaming services

Walk to Old Port ♦ West End Condo ♦ Parking

Walk to Old Port ♦ West End Condo ♦ Parking
West End
9.6 out of 10, Exceptional, (84 reviews)
"Great location and very spacious! Easy commutation - must stay! "
United States
Courtney H.
The price is HK$806
HK$2,946 total
includes taxes & fees
10 Jun - 11 Jun
Walk to Old Port ♦ West End Condo ♦ Parking
Living room

Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (1 review)
"Beautiful new boutique hotel in Portland! Easy access to the Old Port and everything Portland has to offer. Very quiet, clean and well appointed rooms. The kitchen makes all the difference, even for a short stay! We loved our visit so much that we've booked a second trip!"
United States
Allison
The price is HK$3,367
HK$4,846 total
includes taxes & fees
8 Jun - 9 Jun
Evalina Hotel
Fridge, microwave, oven, stovetop

Bright & Spacious Apartment with Amazing Shower

Bright & Spacious Apartment with Amazing Shower
Parkside
8.6 out of 10, Excellent, (19 reviews)
"Wonderful stay! Place was amazing and host is very responsive. Thank you so much "
United States
Logan R.
The price is HK$767
HK$1,477 total
includes taxes & fees
4 Jun - 5 Jun
Bright & Spacious Apartment with 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 Regency Hotel & Spa

Portland Regency Hotel & Spa

6/10 Okay
"The Regency is a Portland institution that's located in a fantastic location. Too bad it's starting to look and sound and smell weathered. We were in room 215 and it smelled of smelly socks when we entered. The ancient air and heating system was on, but it was so loud it was hard to nap, much less sleep. Luckily it wasn't too hot or cold outside; we simply turned it off. I liked the free coffee station in the morning. The British-born valet was very cheerful and helpful. So were the front desk workers, generally, although when I reported the smell in the room and loud heating/cooling system, they just nodded and said it was getting old. You think they would've offered a more profuse apology, or a drink in the bar downstairs on the hotel--it would've been good PR. But nothing. I won't stay here again."
Peter 1-night trip
Posted less than an hour ago
Portland Regency Hotel & Spa

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
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  • 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 Bayside Bowl, 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 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?

Cozy & Quiet Home in Portland Maine. One Bedroom, Private 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 an electric kettle.

How many holiday rentals are there in Portland?

Choose from 85 Expedia holiday rentals in Portland for a memorable holiday.

What can I see and do in Portland?

Bayside Bowl and Portland Observatory 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.