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Top Holiday Rentals in Portland

Charming Studio apartment with WiFi, AC in welcoming Portland

10.0 out of 10, Exceptional, (2)
"This was a great stay through and through. Excellent condition, very responsive before and during the stay, and a great location. 10/10 will recommend to anyone staying in Portland! "
The price is £173
includes taxes & fees
28 Jul - 29 Jul
Charming Studio apartment with WiFi, AC in welcoming Portland

Studio Unit Walkable Everywhere

The price is £136
includes taxes & fees
7 Jul - 8 Jul
Studio Unit Walkable Everywhere

Private Entrance Residential Portland

8.0 out of 10, Very good, (1)
"Great location for seeing the Portland Head Lighthouse. Comfortable bed."
The price is £145
includes taxes & fees
10 Jul - 11 Jul
Private Entrance Residential Portland

Elegant condo - walk to Portland's best restaurants & Old Port

9.4 out of 10, Exceptional, (62)
"Right off a Main Street with tons of food and drink options. Loved the area, felt safe and fun. Close to walking trails as well. Inside decor was nice. "
The price is £338
includes taxes & fees
6 Jul - 7 Jul
Elegant condo - walk to Portland's best restaurants & Old Port

Walkable near downtown 1 Bedroom

The price is £66
includes taxes & fees
21 Jul - 22 Jul
Walkable near downtown 1 Bedroom

Beautiful, Spacious Home, minutes to the Old Port!

10.0 out of 10, Exceptional, (3)
"We stayed for night with couples and friends. We had an amazing time and the place was so clean and exactly as described. "
The price is £352
includes taxes & fees
13 Jul - 14 Jul
Beautiful, Spacious Home, minutes to the Old Port!

Willard Beach–Private Apt Near Portland & Parks

10.0 out of 10, Exceptional, (1)
"Cozy and clean place with a quick walk to the beach in beautiful neighborhood!"
The price is £331
includes taxes & fees
20 Jul - 21 Jul
Willard Beach–Private Apt Near Portland & Parks

Sauna & fire table near Portland's Back Cove

10.0 out of 10, Exceptional, (1)
"Great location, clean property"
The price is £277
includes taxes & fees
10 Jul - 11 Jul
Sauna & fire table near Portland's Back Cove

Luxury on Back Cove - Three Gables

10.0 out of 10, Exceptional, (2)
"GoodLocation, very clean. Would stay again "
The price is £350
includes taxes & fees
6 Jul - 7 Jul
Luxury on Back Cove - Three Gables

Mint Ocean Promenade Condo, Steps to Old Port

The price is £286
includes taxes & fees
8 Jul - 9 Jul
Mint Ocean Promenade Condo, Steps to Old Port

Willard Square Family Home

9.6 out of 10, Exceptional, (7)
"A funky place. Liked the decor. "
The price is £510
includes taxes & fees
6 Jul - 7 Jul
Willard Square Family Home

Beautiful West End Apartment

The price is £398
includes taxes & fees
9 Jul - 10 Jul
Beautiful West End Apartment

Historic Elegance in the Heart of Portland

10.0 out of 10, Exceptional, (1)
"Our son got married in Portland and our large family came to celebrate and participate. The location of this property is superb. It’s funky in the best way. The house was built in 1800! We thoroughly enjoyed our stay. Thank you!"
The price is £3,302
includes taxes & fees
25 Jul - 26 Jul
Historic Elegance in the Heart of Portland

Huge Historic Downtown Townhome

9.8 out of 10, Exceptional, (7)
"From California, I put together a 21st birthday weekend in Portland for my daughter and five of her friends from Bates College. Tim, the manager, was communicative, helpful, and always available. The townhome is adorable, and the location is fantastic."
The price is £520
includes taxes & fees
9 Jul - 10 Jul
Huge Historic Downtown Townhome

1200 sq ft ♦ West End Townhouse ♦ Perfect Location

8.6 out of 10, Excellent, (56)
"Quiet neighborhood. Nice place"
1200 sq ft ♦ West End Townhouse ♦ Perfect Location

Brews, Art & Fun! Downtown Stay Right in the Heart of Portland!

9.0 out of 10, Wonderful, (19)
"We had a great "
The price is £329
includes taxes & fees
27 Jul - 28 Jul
Brews, Art & Fun! Downtown Stay Right in the Heart of Portland!

6BR Sleeps 16 w/ Balcony 10 mins to Downtown

The price is £1,124
includes taxes & fees
8 Jul - 9 Jul
6BR Sleeps 16 w/ Balcony 10 mins to Downtown

Spacious Portland Home + Parking

The price is £830
includes taxes & fees
18 Jul - 19 Jul
Spacious Portland Home + Parking

Amazing West End apartment walkable to downtown and the waterfront.

The price is £730
includes taxes & fees
20 Jul - 21 Jul
Amazing West End apartment walkable to downtown and the waterfront.

Modern & Sunny House Steps from the Promenade. Private Parking!

10.0 out of 10, Exceptional, (29)
"This properly was perfectly suited for my wife and I, it is exactly as it is described. We were comfortable and enjoyed every minute at this property. We had to reschedule our flight which required us staying an extra night, Jennifer so graciously allowed us to stay another night. We would definitely stay here again if we ever return to Portland."
The price is £577
includes taxes & fees
8 Jul - 9 Jul
Modern & Sunny House Steps from the Promenade. Private Parking!
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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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 acclaimed theatre scene and great live music 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 and Quiet beautiful home 1 Bedroom private bathroom Portland with WiFi, AC: This highly rated holiday home rental in Portland is located on the beach, and offers a fireplace, air conditioning and WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave and kitchenware.

How many holiday rentals are there in Portland?

Choose from 143 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.