Top Vacation Homes in Portland in 2025

Check prices for these dates

Next weekend

6 Jum. II - 8 Jum. II

In two weeks

13 Jum. II - 15 Jum. II

In one month

27 Jum. II - 29 Jum. II

In two months

25 Raj. - 27 Raj.

Top Cities in Portland

Winnifred Beach which includes general coastal views as well as a small group of people

Compare 503 Vacation Homes in Portland with updated reviews, rates, and availability.

"Clean and well kept. Exceptional customer service, very accommodating- they went above and beyond to make us comfortable. Gorgeous views from the rooftop pool. Ice cold A/C and fan as well. Tried the fried chicken and oxtail from the restaurant upstairs- both are great. Also had a nice jetted tub in our room. Will be back."

SAR 375 total

includes taxes & fees

2 Jun - 3 Jun

"Me and my family had a wonderful stay here in this home from Dec 23- Jan 7th. Let’s start off by saying the owner Natalie is so sweet and respectful. Inside was so nice and clean, it was very spacious and felt like home. Natalie and her family treated us as if we were her family they were all very welcoming, and if I had any questions or concerns she always was a phone call away. In the area there is a mall and other activities to do things. When we come back for vacation we will definitely book...

SAR 394 total

includes taxes & fees

1 Jun - 2 Jun

"Good property in safe neighborhood, close to many amenities."

"It was great would definitely come there again."

SAR 293 total

includes taxes & fees

7 Jun - 8 Jun

Premium Townhome, 2 Bedrooms, Executive Level | Private kitchen | Full-size fridge, microwave, oven, stovetop

"Not a nice Place"

SAR 933 total

includes taxes & fees

31 May - 1 Jun

"My stay here was awesome. The space was very clean and Kimarly was very friendly and helpful with local recommendations. Responses were quick too. I will definitely book again."

"We had an enjoyable stay just what we needed. The property is in close proximity to mall, dining and supermarket. The area is very quiet which I like."

SAR 773 total

includes taxes & fees

7 Jun - 8 Jun

SAR 791 total

includes taxes & fees

8 Jun - 9 Jun

"The property was beautiful and well kept. The bonus is that it is affordable. Ms. Trudy was the best host. She was accommodating, easy to get to and caring. We enjoyed our stay and you will too. "

"Everything from the check-in to the stay and check-out was superb. Will be back for sure! Lovely home, with comfortable rooms and beds."

SAR 530 total

includes taxes & fees

31 May - 1 Jun

"It was comfortable and communication was great. "

SAR 469 total

includes taxes & fees

8 Jun - 9 Jun

"It was very comfortable it is more suited for a couple and young children. However I did enjoyed my stay. The property owner was very very nice and available. "

SAR 413 total

includes taxes & fees

31 May - 1 Jun