Portland Holiday Rentals

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Check prices for these dates

In two weeks
31 Oct - 2 Nov
In two months
12 Dec - 14 Dec
In three months
9 Jan - 11 Jan
In four months
6 Feb - 8 Feb

Holiday Rentals in Portland

Deluxe Suite, 1 King Bed | Living area
The Weldon Hotel
The Weldon Hotel
4.5 star property
9.8 out of 10, Exceptional, (84)
"Loved this place and would definitely stay here next time we go back."
The price is AU$424
includes taxes & fees
9 Nov - 10 Nov
The Weldon Hotel
Interior
Adorable Portland getaway on the Eastern Promenade
Adorable Portland getaway on the Eastern Promenade
9.8 out of 10, Exceptional, (123)
"So clean! Loved all the little notes, very helpful. Such a great location close to the water and would definitely recommend this place in the future."
The price is AU$322
includes taxes & fees
9 Nov - 10 Nov
Adorable Portland getaway on the Eastern Promenade
Interior
Bright & Sunny West End Apartment with Private Parking.
Bright & Sunny West End Apartment with Private Parking.
10.0 out of 10, Exceptional, (44)
"Adorable apartment for our family of 5 to spend a night. Great location in town. "
The price is AU$533
includes taxes & fees
2 Nov - 3 Nov
Bright & Sunny West End Apartment with Private Parking.
Smart TV
Beautiful 1st Floor Apartment & Amazing Shower
Beautiful 1st Floor Apartment & Amazing Shower
9.0 out of 10, Wonderful, (23)
"Our stay was phenomal!! From the communication with the hosts to the coziness and cleanliness of this place, it was perfect! Highly suggest for a visit, and the location is perfect! Parking sucks, but it’s Portland not the hosts fault!"
The price is AU$276
includes taxes & fees
10 Nov - 11 Nov
Beautiful 1st Floor Apartment & Amazing Shower
TV
Port City Nest: Beautiful 2bd w/ Balcony & Parking
Port City Nest: Beautiful 2bd w/ Balcony & Parking
The price is AU$521
includes taxes & fees
19 Oct - 20 Oct
Port City Nest: Beautiful 2bd w/ Balcony & Parking
Fridge, microwave, oven, stovetop
Luxury on Back Cove - Three Gables
Luxury on Back Cove - Three Gables
10.0 out of 10, Exceptional, (7)
"GoodLocation, very clean. Would stay again "
The price is AU$644
includes taxes & fees
4 Nov - 5 Nov
Luxury on Back Cove - Three Gables
Exterior
Completely remodeled 2 bedroom apartment in Portland's West End
Completely remodeled 2 bedroom apartment in Portland's West End
10.0 out of 10, Exceptional, (76)
"Great place! Perfect size for my family and our dog. Thank you!"
The price is AU$748
includes taxes & fees
28 Oct - 29 Oct
Completely remodeled 2 bedroom apartment in Portland's West End
Exterior
Cozy, Elegant and Bright 2 bed in the East End
Cozy, Elegant and Bright 2 bed in the East End
9.8 out of 10, Exceptional, (48)
"Very nice apartment. Nice area!"
The price is AU$521
includes taxes & fees
12 Nov - 13 Nov
Cozy, Elegant and Bright 2 bed in the East End
TV
East end. Walk to food, beer and downtown fun.
East end. Walk to food, beer and downtown fun.
9.8 out of 10, Exceptional, (32)
"The decor and accommodations were great. We only stayed one night, but certainly would have loved more time. The location was central to many downtown spots. The host was very responsive and informative. "
The price is AU$493
includes taxes & fees
2 Nov - 3 Nov
East end. Walk to food, beer and downtown fun.
Property grounds
State of Charm | Historic West End Haven
State of Charm | Historic West End Haven
9.2 out of 10, Wonderful, (5)
The price is AU$751
includes taxes & fees
6 Nov - 7 Nov
State of Charm | Historic West End Haven
Dining
Sunny Spot with Private Parking.
Sunny Spot with Private Parking.
2.0 star property
9.8 out of 10, Exceptional, (23)
"Wonderful stay!"
The price is AU$313
includes taxes & fees
16 Nov - 17 Nov
Sunny Spot with Private Parking.
Exterior detail
1200 Sq Ft ♦ West End Gem ♦ Perfect Location
1200 Sq Ft ♦ West End Gem ♦ Perfect Location
9.4 out of 10, Exceptional, (96)
"The house is good and reasonably appointed for a short stay. Beds quite comfortable and home is clean You can walk to downtown port area easily. Very peaceful residential street. Enjoyed our short visit. "
The price is AU$417
includes taxes & fees
3 Nov - 4 Nov
1200 Sq Ft ♦ West End Gem ♦ Perfect Location
Dining
Chic 3 BR Retreat- Prime Old Port Spot with parking- Park and walk the town
Chic 3 BR Retreat- Prime Old Port Spot with parking- Park and walk the town
9.8 out of 10, Exceptional, (159)
"Easy parking and walkable to many of the great locations in Portland! Very easy communication."
The price is AU$1,402
includes taxes & fees
20 Oct - 21 Oct
Chic 3 BR Retreat- Prime Old Port Spot with parking- Park and walk the town
Exterior detail
Glorious getaway on Portland's Eastern Promenade.
Glorious getaway on Portland's Eastern Promenade.
9.8 out of 10, Exceptional, (169)
"We enjoyed our stay and would book again."
The price is AU$496
includes taxes & fees
2 Nov - 3 Nov
Glorious getaway on Portland's Eastern Promenade.
On the beach, sun-loungers, beach towels
Step right out to the beach! Amazing location 7 min to Portland. Unit 4
Step right out to the beach! Amazing location 7 min to Portland. Unit 4
10.0 out of 10, Exceptional, (13)
"Great area, close to the beach, water views, close to Portland, and everything in the apartment worked really well. There has been a lot of attention paid as to what would make a guest's stay really awesome. "
The price is AU$899
includes taxes & fees
2 Nov - 3 Nov
Step right out to the beach! Amazing location 7 min to Portland. Unit 4
Fridge, microwave, oven, stovetop
Bright & Spacious Apartment with Amazing Shower
Bright & Spacious Apartment with Amazing Shower
8.6 out of 10, Excellent, (14)
"Amazing property. Have stayed here before and hosts always have amazing communication. Place was in immaculate condition. Thank you!"
The price is AU$285
includes taxes & fees
12 Nov - 13 Nov
Bright & Spacious Apartment with Amazing Shower
Fridge, microwave, oven, stovetop
Huge Historic Downtown Townhome
Huge Historic Downtown Townhome
9.8 out of 10, Exceptional, (8)
"We gathered as a family to spend one night in Portland and we could not have been happier with the location. "
The price is AU$877
includes taxes & fees
16 Nov - 17 Nov
Huge Historic Downtown Townhome
Property grounds
Amazing West End apartment walkable to downtown and the waterfront.
Amazing West End apartment walkable to downtown and the waterfront.
10.0 out of 10, Exceptional, (1)
"We really enjoyed our visit! The apartment was very charming, with spacious bedrooms, and it included everything we needed for our vacation. We would certainly rent this unit again! "
The price is AU$907
includes taxes & fees
2 Nov - 3 Nov
Amazing West End apartment walkable to downtown and the waterfront.
Outdoor dining
Skyline 138: Charming West End Mansard Penthouse
Skyline 138: Charming West End Mansard Penthouse
9.2 out of 10, Wonderful, (22)
"Nice easy process, clean place, cute decor, easy to walk and uber to hot spots we wanted to see"
The price is AU$697
includes taxes & fees
16 Nov - 17 Nov
Skyline 138: Charming West End Mansard Penthouse
Microwave, oven, coffee/tea maker, cookware/dishes/utensils
Walk to Old Port ♦ West End Condo ♦ Parking
Walk to Old Port ♦ West End Condo ♦ Parking
9.6 out of 10, Exceptional, (77)
"Cute place, close to old port! We brought our pup and she was happy as well. We would definitely stay there again! "
The price is AU$425
includes taxes & fees
3 Nov - 4 Nov
Walk to Old Port ♦ West End Condo ♦ 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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Top Portland Hotel Reviews

Hampton Inn Portland Downtown - Waterfront

Hampton Inn Portland Downtown - Waterfront

10/10 Excellent
"The Hampton Inn Portland Downtown Waterfront is in an excellent location near Old Port and the waterfront restaurants. It was very easy to retreat to our room during the day to cool down and relax in between sightseeing and shopping. The parking is weirdly expensive for such a hotel, but the valets were professional and easy to work with."
Timothy 2-night trip
Posted 3 days ago
Hampton Inn Portland Downtown - Waterfront

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 favourite 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 depend 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 AU$242 per night. Entering your travel dates in the search wizard might find you 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. 

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 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 Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.: This highly rated holiday home rental in Portland is located on the beach, and offers a fireplace, air conditioning and free WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave and kitchenware. Our travellers also rate Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port as a favourite home for rent in Portland.

How many holiday rentals are there in Portland?

Choose from 85 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.