Portland Holiday Rentals

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Holiday Rentals in Portland

Rent a room in the gorgeous Holt House
8.4 out of 10, Very good, (19)
"It was a great trip up to Portland and the property met our needs."
Rent a room in the gorgeous Holt House
Glorious getaway on Portland's Eastern Promenade.
10.0 out of 10, Exceptional, (124)
"We really enjoyed our stay. We loved being able to walk to the Eastern Promenade. The beds, including the sofa bed were very comfortable. Very cute and cozy There are stairs to enter the building for anyone with mobility issues. If you are unfamiliar with older buildings, the radiators do make some noise while heating in the winter."
The price is NZ$498
per night
16 May - 17 May
Glorious getaway on Portland's Eastern Promenade.
Elegant condo - walk to Portland's best restaurants & Old Port
9.4 out of 10, Exceptional, (45)
"The kitchen was very well equipped. Living room was so cozy with the fire. Bed was super comfortable. The unit has really tall ceilings and is cozy. Only issue was the dog upstairs. They kept barking and whining."
Elegant condo - walk to Portland's best restaurants & Old Port
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Inviting apartment with full kitchen, porch, convenient location, & fast WiFi
8.0 out of 10, Very good, (5)
"This home was clean, bright and comfortable. Great location, no issues. Would definitely stay here again."
Inviting apartment with full kitchen, porch, convenient location, & fast WiFi
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
9.4 out of 10, Exceptional, (21)
"Stayed for a weekend for bachelorette party! Very clean, close to downtown and loved the hot tub."
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
The Globe House on Munjoy Hill - Amazing Sunsets - Walk to Breweries
10.0 out of 10, Exceptional, (51)
"Comfortable, clean, very well decorated apartment in a pleasant, walkable neighborhood. I highly recommend this property."
The Globe House on Munjoy Hill - Amazing Sunsets - Walk to Breweries
Adorable Portland getaway on the Eastern Promenade
9.8 out of 10, Exceptional, (75)
"This is a lovely little apartment, and we were very comfortable. I agree with the owner’s statement about the steps being steep; there is no landing at the top of these steps. We brought smaller bags, and that helped! I wouldn’t attempt this with a baby or a toddler. Everybody else: enjoy!"
The price is NZ$416
per night
20 May - 21 May
Adorable Portland getaway on the Eastern Promenade
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
8.8 out of 10, Excellent, (20)
"Clean and easy to access, nice property for a short stay. Easy communication."
The price is NZ$636
per night
20 May - 21 May
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
2 duplex
3.0 star property
The price is NZ$455
per night
18 May - 19 May
2 duplex
Gorgeous ocean-front home with stunning beach views
9.6 out of 10, Exceptional, (74)
"Great little condo. Right on the beach! Balcony is wonderful, as is the view from the master. Second bedroom is definitely a “kids” room with the two bunk beds. Garage was great for a car, would not fit the height of a truck"
Gorgeous ocean-front home with stunning beach views
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
9.8 out of 10, Exceptional, (174)
"Even with a snow/ice storm, the beach doesn’t disappoint! Beautiful sunrises, sunsets, and waves crashing. The condo was warm and cozy and I was very happy to be able to watch the Bruins on tv. Already planned my next visit!"
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
100 feet from the ocean 3 bedroom cottage 420 friendly
9.2 out of 10, Wonderful, (13)
"The property was great and a very convenient location to the beach, shops, and pier. They have everything you could possibly need except food and clothing! Very clean, TVs and ACs in every room. The only challenge as others mentioned is parking. It is a tight fit and if your tires are on the sidewalk you can be ticketed. On our second to last day we were approached by the parking patrol and told this. He was super nice and said he wouldn't ticket us but another may. I said we were leaving the...
100 feet from the ocean 3 bedroom cottage 420 friendly
Oceanfront Condo! Spectacular Views From Private Large Balcony
9.0 out of 10, Wonderful, (112)
"Very clean and comfortable! We loved our time there!"
The price is NZ$897
per night
16 May - 17 May
Oceanfront Condo! Spectacular Views From Private Large Balcony
Everybody's favorite Maine beach location
9.2 out of 10, Wonderful, (12)
"The property was updated and very clean. The pillows were not very good, but the bed was great! The location was not where we anticipated. It was very easy checking in and out."
Everybody's favorite Maine beach location
Large 2BD cottage 10 min to Pier & Beach Pets ok
9.2 out of 10, Wonderful, (15)
"The house was cozy and well equipped. We had a wonderful time."
The price is NZ$464
per night
20 May - 21 May
Large 2BD cottage 10 min to Pier & Beach Pets ok
Little Miss Cottages
2.5 star property
8.2 out of 10, Very good, (68)
"Perfect place for a family to stay for a fair price if you want to stay a few nights and tour around the rest of Maine. Beach was wonderful! "
Little Miss Cottages
Third-Floor Coastal Condo W/ Modern Updates, High-Speed WiFi & Perfect Location
7.4 out of 10, Good, (25)
"The unit has a really nice view of downtown and the pier. Cool view of the ferris wheel lit up at night. At first glance, the unit is nicely decorated. However, it needs to be refreshed - there are chunks missing out of the walls, things falling apart, ongoing water damage next to the tub. Maintenance from the building came by on the first morning of the stay to check on the kitchen sink because there was a massive leak happening to the unit below. Overall, it seemed as if no one has been...
Third-Floor Coastal Condo W/ Modern Updates, High-Speed WiFi & Perfect Location
Historic Kennebunkport home only 0.3 miles to Dock Square
10.0 out of 10, Exceptional, (45)
"Very impressed with location, cleanliness, decor, and little extras like bottled water, bottle of wine, truffles in bedrooms as well as easy communications with Katie!"
The price is NZ$825
per night
23 May - 24 May
Historic Kennebunkport home only 0.3 miles to Dock Square
2 min walk to the beach. Pet friendly condo
9.0 out of 10, Wonderful, (22)
"Great place to stay"
The price is NZ$342
per night
16 May - 17 May
2 min walk to the beach. Pet friendly condo
East Grand Ave Fabulous Cottage
9.0 out of 10, Wonderful, (110)
"Good location, owner was very responsive to our needs."
East Grand Ave Fabulous Cottage
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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.

Other types of properties in Portland you may be interested in

The Westin Portland Harborview
4.0 star property
8.6 out of 10, Excellent, (1054)
"The Westin is very conveniently located in downtown Portland. Great harbor view and wonderful staff."
The price is NZ$282
per night
28 May - 29 May
The Westin Portland Harborview
Portland Harbor Hotel
4.0 star property
9.0 out of 10, Wonderful, (1187)
"Rooms are nice, beds a little too hard, employees not very friendly. I did like you can get coffee in the morning in the lobby. Breakfast not so good. "
The price is NZ$344
per night
19 May - 20 May
Portland Harbor Hotel
Canopy by Hilton Portland Waterfront
4.0 star property
9.4 out of 10, Exceptional, (641)
"Wonderful place to stay. Spotlessly clean, great decor, exceptionally nice staff. Very good location. "
The price is NZ$448
per night
20 May - 21 May
Canopy by Hilton Portland Waterfront
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.

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.

How many holiday rentals are there in Portland?

Choose from 117 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 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.