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Portland Holiday Rentals

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Our top choices for Portland holiday rentals

Private Entrance Residential Portland

Private Entrance Residential Portland
Deering Center
8.4 out of 10, Very good, (7 reviews)
"This was a great place to stay. Easy to get to all of our destinations. Place was clean and comfortable. Would stay here again. "
United States
Ameleah B.
The price is NZ$321
includes taxes & fees
2 July - 3 July
Private Entrance Residential Portland

Studio Apartment near downtown Walkable!

Studio Apartment near downtown Walkable!
West Bayside
8.6 out of 10, Excellent, (8 reviews)
"Maine Oyster Company was a highlight of the trip! "
United Kingdom
Tyler P.
The price is NZ$341
includes taxes & fees
5 July - 6 July
Studio Apartment near downtown Walkable!

Spacious and Contemporary Condo in the Heart of Portland - Close to Beach

Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
East Bayside
8.8 out of 10, Excellent, (38 reviews)
"Overall a pleasing stay."
United States
Mallory D.
The price is NZ$809
includes taxes & fees
6 July - 7 July
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach

1-bedroom hotel suites in Scarborough with essentially stocked kitchens.

1-bedroom hotel suites in Scarborough with essentially stocked kitchens.
South Portland
10.0 out of 10, Exceptional, (2 reviews)
"We really appreciated our stay!"
United States
Anonymous traveller
The price is NZ$402
includes taxes & fees
2 July - 3 July
1-bedroom hotel suites in Scarborough with essentially stocked kitchens.

Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
9.8 out of 10, Exceptional, (27 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 NZ$705
includes taxes & fees
6 July - 7 July
Sunny Spot with Private Parking.

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

Elegant condo - walk to Portland's best restaurants & Old Port
East Bayside
9.2 out of 10, Wonderful, (80 reviews)
"Lovely unit. Very comfortable bed. Nice to have off street parking. Walkable to Old Port. Would def stay again. "
United States
Erin H.
The price is NZ$879
includes taxes & fees
6 July - 7 July
Elegant condo - walk to Portland's best restaurants & Old Port

Charming Studio apartment with WiFi, AC in welcoming Portland

Charming Studio apartment with WiFi, AC in welcoming Portland
Munjoy Hill
9.6 out of 10, Exceptional, (15 reviews)
"Great place! We would definitely return if we were in the area."
United States
Preston
The price is NZ$540
includes taxes & fees
14 July - 15 July
Charming Studio apartment with WiFi, AC in welcoming Portland

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 NZ$790
includes taxes & fees
2 July - 3 July
Fortland Island Campground

The Coastal Connection

The Coastal Connection
Thorton Heights
9.0 out of 10, Wonderful, (2 reviews)
"Very convenient, comfortable, and bright apartment. We appreciated that dogs were allowed as well."
United States
Sheryl S.
The price is NZ$735
includes taxes & fees
2 July - 3 July
The Coastal Connection

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

Historic Home in the West End. Private Parking.

Historic Home in the West End. Private Parking.
West End
10.0 out of 10, Exceptional, (57 reviews)
"Place was beautiful walking distance to everything check-in was great parking was great."
United States
TJS S.
Historic Home in the West End. Private Parking.

Walk to Back Cove | Smart TV | Wi-Fi | Parking

Walk to Back Cove | Smart TV | Wi-Fi | Parking
Oakdale
Walk to Back Cove | Smart TV | Wi-Fi | Parking

The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (101 reviews)
"Lovely suite! Comfy king bed, everything spotless, Great location. Would stay here again"
United States
Roberta
The price is NZ$690
includes taxes & fees
8 July - 9 July
The Weldon Hotel

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, (103 reviews)
"Lovely view and accessibility to the Old Port area. Enjoyed our relaxing stay! Thanks Dan! "
United States
David E.
The price is NZ$814
includes taxes & fees
5 July - 6 July
Ocean View East End Studio in a Historic Victorian

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 NZ$772
includes taxes & fees
12 July - 13 July
Peaceful & minutes from the Old Port with private parking

THE RALEIGH BnB APARTMENT SELF CHECK-IN / Free Off-Street Parking

THE RALEIGH BnB APARTMENT SELF CHECK-IN / Free Off-Street Parking
Munjoy Hill
10.0 out of 10, Exceptional, (4 reviews)
"Great place, so close to everything and a clean, quiet spot to sleep."
United States
Dan K.
The price is NZ$864
includes taxes & fees
14 July - 15 July
THE RALEIGH BnB APARTMENT SELF CHECK-IN / Free Off-Street Parking

1200 Sq Ft ♦ West End Gem ♦ Perfect Location

1200 Sq Ft ♦ West End Gem ♦ Perfect Location
West End
9.4 out of 10, Exceptional, (102 reviews)
"Communication with the host was very good . The house was older than expected . Sheets on sofa bed were soiled , but we had additional clean sheets to use. Kitchen would benefit from being better stocked . (Additional dish towels, sponge missing , additional frying pan .) Steps to the kitchen , bathroom and bedroom are steep . Street parking available …."
United States
Maria Pilar
The price is NZ$698
includes taxes & fees
20 July - 21 July
1200 Sq Ft ♦ West End Gem ♦ Perfect Location

Walk to Old Port ♦ West End Condo ♦ Parking

Walk to Old Port ♦ West End Condo ♦ Parking
West End
9.6 out of 10, Exceptional, (86 reviews)
"Great location and very spacious! Easy commutation - must stay! "
United States
Courtney H.
The price is NZ$756
includes taxes & fees
14 July - 15 July
Walk to Old Port ♦ West End Condo ♦ Parking

Willard Beach–Apartment Near Portland & Parks

Willard Beach–Apartment Near Portland & Parks
Willard Beach
10.0 out of 10, Exceptional, (5 reviews)
"Excellent in every way."
United States
Robert B.
Willard Beach–Apartment Near Portland & Parks

Cozy Two Bedroom on Munjoy Hill

Cozy Two Bedroom on Munjoy Hill
Munjoy Hill
The price is NZ$518
includes taxes & fees
14 July - 15 July
Cozy Two Bedroom on Munjoy Hill
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

Find out more about Portland

Everything you need to know about Portland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Portland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Portland holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Portland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Portland. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Portland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Portland holiday rentals we have selected for you start as low as NZ$319 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Portland rentals

At Expedia, we put the best Portland holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Portland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Portland holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Portland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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 acclaimed theatre scene 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 Maine. One Bedroom, Private Bathroom “No Kitchen”: This highly rated holiday home rental in Portland is located on the beach, and offers a fireplace, air conditioning and a Smart TV 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.