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Portland Holiday Rentals

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Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sept - 13 Sept
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Portland holiday rentals

Interior

2-Bedroom Apartment Steps from Eastern Prom - Walk to Everything!

2-Bedroom Apartment Steps from Eastern Prom - Walk to Everything!
Munjoy Hill
2-Bedroom Apartment Steps from Eastern Prom - Walk to Everything!
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)
"Apartment was very cute, clean, and just what I was looking for. Jennifer was very accommodating and understanding "
United States
Jolee S.
The price is HK$2,179
HK$3,426 total
includes taxes & fees
21 Jul - 22 Jul
Peaceful & minutes from the Old Port with private parking
Interior

Skyline 138: Charming West End Mansard Penthouse

Skyline 138: Charming West End Mansard Penthouse
Parkside
9.4 out of 10, Exceptional, (31 reviews)
"Great place. Had everything we needed and close to everything."
United States
Bill P.
The price is HK$2,379
HK$4,370 total
includes taxes & fees
19 Jul - 20 Jul
Skyline 138: Charming West End Mansard Penthouse
Egyptian cotton sheets, premium bedding, down duvets, bed sheets

Fortland Island Campground

Fortland Island Campground
1.0 star property
Portland
10.0 out of 10, Exceptional, (3 reviews)
"It was very quiet and liked the experience of staying in a camp like setting."
United States
leela srinivas
The price is HK$1,759
HK$1,918 total
includes taxes & fees
19 Jul - 20 Jul
Fortland Island Campground
Interior

Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
9.8 out of 10, Exceptional, (29 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$1,913
HK$3,016 total
includes taxes & fees
20 Jul - 21 Jul
Sunny Spot with Private Parking.
Exterior

Ocean View East End Studio in a Historic Victorian

Ocean View East End Studio in a Historic Victorian
Portland
9.8 out of 10, Exceptional, (104 reviews)
"Lovely view and accessibility to the Old Port area. Enjoyed our relaxing stay! Thanks Dan! "
United States
David E.
The price is HK$2,352
HK$3,666 total
includes taxes & fees
2 Aug - 3 Aug
Ocean View East End Studio in a Historic Victorian
Exterior

Luxury Condo Downtown Portland Old Port

Luxury Condo Downtown Portland Old Port
Downtown Portland
9.4 out of 10, Exceptional, (20 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 HK$2,406
HK$3,878 total
includes taxes & fees
29 Jul - 30 Jul
Luxury Condo Downtown Portland Old Port
Beach

Island View House BnB Self Check-In # 4 / Free Off-Street Parking

Island View House BnB Self Check-In # 4 / Free Off-Street Parking
Munjoy Hill
9.8 out of 10, Exceptional, (15 reviews)
"Great space in a nice neighborhood location. "
United States
Sheila G.
The price is HK$2,352
HK$4,349 total
includes taxes & fees
20 Jul - 21 Jul
Island View House BnB Self Check-In # 4 / Free Off-Street Parking
Private kitchen

The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (102 reviews)
"Spacious with plenty of room for my family of four. Excellent kitchen, washer and dryer and stellar location close to Waterfront district."
United States
Kara
The price is HK$3,263
HK$4,144 total
includes taxes & fees
28 Jul - 29 Jul
The Weldon Hotel
Dining

Charming West End Hideaway. Private Parking

Charming West End Hideaway. Private Parking
West End
10.0 out of 10, Exceptional, (53 reviews)
"Great stay. The apartment is cute, clean, and in a perfect location. Parking was easy, and the mattress was very comfortable. Would definitely stay here again."
United States
Victoria M.
The price is HK$2,171
HK$3,273 total
includes taxes & fees
20 Jul - 21 Jul
Charming West End Hideaway. Private Parking
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, (38 reviews)
"Clean, great location, excellent communication with host, perfectly furnished for our group"
United States
Elizabeth P.
The price is HK$2,791
HK$4,216 total
includes taxes & fees
17 Aug - 18 Aug
East end. Walk to food, beer and downtown fun.
Exterior

Spacious 3 BR in Portland's Libbytown!

Spacious 3 BR in Portland's Libbytown!
Portland
9.6 out of 10, Exceptional, (50 reviews)
"Really cute, clean place that was a short drive to everything!"
United States
Annalise E.
The price is HK$2,587
HK$4,204 total
includes taxes & fees
20 Jul - 21 Jul
Spacious 3 BR in Portland's Libbytown!
Outdoor dining

Parkside Victorian 2BR — walk to Old Port, off-street parking, balcony

Parkside Victorian 2BR — walk to Old Port, off-street parking, balcony
Parkside
10.0 out of 10, Exceptional, (3 reviews)
"Location was perfect for our needs , exploring Portland! Easy check in process.Very clean !"
United States
veggies 2.
Parkside Victorian 2BR — walk to Old Port, off-street parking, balcony
Living area

SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11

SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11
Ligonia
10.0 out of 10, Exceptional, (1 review)
"Incredibly welcoming house! Very nicely furnished and prepared for guests. Couldn’t be more grateful for the thoughtfulness and accessibility to the property. We kept saying how impressed we were with how many towels were available! A lot of small details were paid attention to by the host! Thank you so much!"
United States
Patrick S.
SAUNA - Spacious and Centrally Located! Two Connected Apartments- Sleeps 11
TV, offices

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.
2BR Apt | Full Kitchen | 10 Min to Old Port
Exterior

Luxury on Back Cove - Three Gables

Luxury on Back Cove - Three Gables
Rosemont
10.0 out of 10, Exceptional, (9 reviews)
The price is HK$1,939
HK$4,583 total
includes taxes & fees
19 Jul - 20 Jul
Luxury on Back Cove - Three Gables
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, (87 reviews)
"It was what we were looking for- in Portland, with a parking spot. Some nice restaurants nearby- walking distance! Note the bathroom is on the first floor, bedrooms are on second. Modest but had everything we needed! What we were disappointed in was we had no idea how many museums and local attractions in a city are closed till the end of April or May! "
United States
Susan R.
Walk to Old Port ♦ West End Condo ♦ Parking
Smart TV, fireplace

Local Landmark! Gorgeous Historic Home

Local Landmark! Gorgeous Historic Home
West End
9.8 out of 10, Exceptional, (12 reviews)
"Very nice apartment in downtown Portland. Clean, bright, had everything we needed. Would stay again."
United States
Honnie B.
The price is HK$2,887
HK$5,309 total
includes taxes & fees
20 Jul - 21 Jul
Local Landmark! Gorgeous Historic Home
Coffee/tea maker, fridge, microwave, oven

Harborview - Curated East End Escape w/ Parking

Harborview - Curated East End Escape w/ Parking
Munjoy Hill
10.0 out of 10, Exceptional, (12 reviews)
"It was a beautiful property with everything you could need available. There were a lot of little touches that made it really nice! "
United States
Jeannette B.
The price is HK$5,252
HK$7,810 total
includes taxes & fees
27 Jul - 28 Jul
Harborview - Curated East End Escape w/ Parking
Exterior detail

Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (138 reviews)
"Owner was so accommodating!"
United States
Kiernan
The price is HK$2,093
HK$3,127 total
includes taxes & fees
30 Jul - 31 Jul
Adorable Portland getaway on the Eastern Promenade
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

Fireside Inn & Suites Portland

Fireside Inn & Suites Portland

10/10 Excellent
"Great hotel with a really nice outdoor pool."
David 2-night trip
Posted 3 hours ago
Fireside Inn & Suites Portland

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
  • Use the map to find apartments and other holiday homes in the Portland neighbourhood you prefer
  • 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 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 great live music 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?

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 free WiFi 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 89 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.