Portland Holiday Rentals

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Holiday Rentals in Portland

Aparthotel in Downtown Portland

4.5 star property
9.8 out of 10, Exceptional, (88)
"Loved this place and would definitely stay here next time we go back."
United States
Eleni
The price is AU$422
includes taxes & fees
7 Dec - 8 Dec
The Weldon Hotel

Holiday Home in East Deering

10.0 out of 10, Exceptional, (65)
"Nice stay. Good amenities. "
United States
Laura H.
The price is AU$1,659
includes taxes & fees
1 Dec - 2 Dec
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

Apartment in Deering Center

9.2 out of 10, Wonderful, (5)
"Great location for seeing the Portland Head Lighthouse. Comfortable bed."
United States
Michelle S.
Private Entrance Residential Portland

Apartment in West Bayside

5.8 out of 10, (7)
"We didn't stay there at all. Canceled reservation "
United States
Dianne
The price is AU$241
includes taxes & fees
8 Dec - 9 Dec
Studio Unit Walkable Everywhere

Apartment in West Bayside

8.6 out of 10, Excellent, (16)
"Host was very accommodating. Apartment worked well for. Description accurate. Would stay again."
United Kingdom
Martha F.
The price is AU$241
includes taxes & fees
2 Dec - 3 Dec
In-town no frills 2 bedroom apt

Condo in Munjoy Hill

9.8 out of 10, Exceptional, (52)
"Excellent stay and location"
United States
David M.
The price is AU$565
includes taxes & fees
31 Dec - 1 Jan 2026
Cozy, Elegant and Bright 2 bed in the East End

Apartment in Parkside

8.8 out of 10, Excellent, (25)
"Clean and comfortable in a great location. Walking distance to the Portland Farmer’s Market on Saturdays. Easy to access and very handy off street parking. Team was very easy to work with. "
United States
Natalie R.
The price is AU$476
includes taxes & fees
8 Dec - 9 Dec
Knock on Wood | Airy Charm in Heart of Downtown

Holiday Home in Back Cove

9.2 out of 10, Wonderful, (19)
"Wonderful view, great park, spacious home, well-appointed... all the things you wish for in a Maine vacation!"
United States
Ben M.
Beautiful, single story ranch. Next to city park with ocean view!

Condo in Downtown Portland

9.6 out of 10, Exceptional, (21)
"We loved the walkable neighborhood & had a great, comfortable stay!"
United States
Erin R.
The price is AU$570
includes taxes & fees
1 Dec - 2 Dec
Gem on Congress - King Bed, Free Parking, Dog & Family Friendly, Modern Condo

Holiday Home in Portland

9.8 out of 10, Exceptional, (22)
"Excellent home overall! Great equipment, great kitchen, great pool, nice patio! Easy access to the home and driveway! Probably the best house I’ve stayed in ! "
United States
Justin J.
Back yard paradise

Condo in East Deering

9.8 out of 10, Exceptional, (122)
"I loved staying in the vacation rental! There was a lot of space, a nice waterfront view, and it was convenient to get in/out of town. "
United States
Jade G.
The price is AU$477
includes taxes & fees
1 Dec - 2 Dec
City Amenities, Casco Bay Sunrises and Natural Beauty

Apartment in Munjoy Hill

9.6 out of 10, Exceptional, (125)
"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."
United States
Lorena
The price is AU$251
includes taxes & fees
1 Dec - 2 Dec
Adorable Portland getaway on the Eastern Promenade

Apartment in Parkside

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"
United States
Faith E.
The price is AU$527
includes taxes & fees
1 Dec - 2 Dec
Skyline 138: Charming West End Mansard Penthouse

Holiday Home in Portland

Cozy Coveside Island Retreat

Holiday Home in Goose Rocks Beach

9.8 out of 10, Exceptional, (138)
"Absolutely beautiful surroundings and cozy place made for an unforgettable experience! "
United States
Sara S.
Quintessential Maine Beach Cottage

Holiday Home in Old Orchard Beach

9.8 out of 10, Exceptional, (45)
"Excellent family stay. Backyard is nice and shaded, you can see the ocean from the house and amenities are great. "
United States
Danielle N.
Private, 2nd Floor Cottage with Wonderful Ocean Views- Perfect for Families!

Holiday Home in Old Orchard Beach

9.8 out of 10, Exceptional, (97)
"The location was perfect and the house was exceptional. The host and property manager were very responsive and helpful. Would definitely recommend a stay!"
United States
Kathleen C.
The price is AU$1,725
includes taxes & fees
3 Dec - 4 Dec
Perfect for Families & friends re-unions! Outdoor Hot Tub, 50 yards to the beach!

Holiday Home in Old Orchard Beach

9.6 out of 10, Exceptional, (67)
"In one word AMAZING! We rented this property to gather our immediate family, adult children and grandchildren. We had a tragedy in our family as my oldest son was killed, this made our once close family, split apart. This property was so beautiful and such a happy place to be that my prayers were answered my family began the healing process. The location and the views one could not be unhappy. Thank you Jason for helping to make the stay amazing!"
United States
Helen F.
The price is AU$2,688
includes taxes & fees
5 Dec - 6 Dec
Sensational Beachfront Property Old Orchard Beach, with indoor elevator

Holiday Home in Kennebunkport

10.0 out of 10, Exceptional, (75)
"Quaint in a great location!"
United States
Shaun M.
The price is AU$943
includes taxes & fees
1 Dec - 2 Dec
Historic Kennebunkport home only 0.3 miles to Dock Square

Cabin in Raymond

10.0 out of 10, Exceptional, (48)
"We loved this cabin! A stone throw from the lake. Private and quiet. "
United States
Kathy K.
Sebago Lake Cottage on Raymond Cape
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 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$241 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. 

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 fascinating museums 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?

Quintessential Maine Beach Cottage: This holiday home rental outside of Portland is located on the beach, and has a private garden, a selection of games and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a full-sized fridge, a dishwasher and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Portland?

Choose from 88 Expedia holiday rentals in Portland for a memorable holiday.

What can I see and do in Portland?

Bayside Bowl and Maine Narrow Gauge Railroad Company and Museum 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.