Portland Holiday Rentals

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Check prices for these dates

In two weeks
26 Sept - 28 Sept
In two months
7 Nov - 9 Nov
In three months
5 Dec - 7 Dec
In four months
2 Jan - 4 Jan

Holiday Rentals in Portland

Our top choices for Portland holiday rentals

The Weldon Hotel
Living area

The Weldon Hotel

4.5 star property
9.8 out of 10, Exceptional, (77)
"Absolutely beautiful place to stay. "
The price is S$538
includes taxes & fees
29 Sept - 30 Sept
The Weldon Hotel
The Cottages at Cabot Cove
Living area

The Cottages at Cabot Cove

3.5 star property
9.6 out of 10, Exceptional, (37)
"Beautiful, charming and staff was excellent "
The price is S$637
includes taxes & fees
16 Sept - 17 Sept
The Cottages at Cabot Cove
68 East Grand Ave
Private kitchen

68 East Grand Ave

3.0 star property
8.6 out of 10, Excellent, (9)
"Property was very nice and close to the beach. Would stay there again. The front desk was extremely helpful as well. "
68 East Grand Ave
Little Miss Cottages
Property grounds

Little Miss Cottages

2.5 star property
8.4 out of 10, Very good, (88)
"Cute and tidy cottage, easy walk to beautiful beach."
Little Miss Cottages
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

Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

10/10 Excellent
"Private balcony is great! My daughter loved it!"
Michelle 1-night trip
Posted 2 days ago
Ramada Plaza by Wyndham Portland

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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 entertainment choices and great live music are some other things you might like to check out during your trip.

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?

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, Fore Street Gallery and Casco Bay Lines Ferry Terminal 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.