Holiday Rentals in Portland

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May 9 - May 10
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May 10 - May 11
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May 10 - May 12
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May 17 - May 19

Holiday Rentals in Portland

Fridge, microwave, oven, stovetop
The Globe House on Munjoy Hill - Amazing Sunsets - Walk to Breweries
10.0 out of 10, Exceptional, (51)
"Comfortable, clean, very well decorated apartment in a pleasant, walkable neighborhood. I highly recommend this property."
The Globe House on Munjoy Hill - Amazing Sunsets - Walk to Breweries
Property grounds
Glorious getaway on Portland's Eastern Promenade.
10.0 out of 10, Exceptional, (124)
"We really enjoyed our stay. We loved being able to walk to the Eastern Promenade. The beds, including the sofa bed were very comfortable. Very cute and cozy There are stairs to enter the building for anyone with mobility issues. If you are unfamiliar with older buildings, the radiators do make some noise while heating in the winter."
The price is €287
per night
16 May - 17 May
Glorious getaway on Portland's Eastern Promenade.
Fridge, microwave, oven, stovetop
Historic Kennebunkport home only 0.3 miles to Dock Square
10.0 out of 10, Exceptional, (45)
"Very impressed with location, cleanliness, decor, and little extras like bottled water, bottle of wine, truffles in bedrooms as well as easy communications with Katie!"
The price is €594
per night
16 May - 17 May
Historic Kennebunkport home only 0.3 miles to Dock Square
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3 bedrooms, desk, iron/ironing board, travel crib
Beach House ∆ Prime Location ∆ Steps to the Ocean
10.0 out of 10, Exceptional, (35)
"The cottage was very nice but the write-up was a little misleading. For example ocean views are very limited—mostly see rooftops, half bath was on ground floor, and stairs to main living area."
The price is €714
per night
6 Jun - 7 Jun
Beach House ∆ Prime Location ∆ Steps to the Ocean
Property grounds
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
10.0 out of 10, Exceptional, (94)
"We celebrated our Mom’s 70th birthday in this beautiful space. It exceeded our expectations and the property manager David is the best!"
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
Fridge, microwave, oven, coffee/tea maker
4 min walk to the beach. Large 1BD Pets Ok
10.0 out of 10, Exceptional, (6)
"Our manager was available and very accommodating to our needs. I would recommend this rental to anyone."
The price is €208
per night
20 May - 21 May
4 min walk to the beach. Large 1BD Pets Ok
View from property
Adorable Portland getaway on the Eastern Promenade
9.8 out of 10, Exceptional, (75)
"This is a lovely little apartment, and we were very comfortable. I agree with the owner’s statement about the steps being steep; there is no landing at the top of these steps. We brought smaller bags, and that helped! I wouldn’t attempt this with a baby or a toddler. Everybody else: enjoy!"
The price is €240
per night
14 May - 15 May
Adorable Portland getaway on the Eastern Promenade
Beach/ocean view
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
9.8 out of 10, Exceptional, (174)
"Even with a snow/ice storm, the beach doesn’t disappoint! Beautiful sunrises, sunsets, and waves crashing. The condo was warm and cozy and I was very happy to be able to watch the Bruins on tv. Already planned my next visit!"
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
Beach nearby, sun-loungers, beach umbrellas, beach towels
Quintessential Maine Beach Cottage
9.8 out of 10, Exceptional, (86)
"Right near Goose Rocks Beach, quiet, clean, peaceful getaway overlooking a salt marsh."
Quintessential Maine Beach Cottage
Property grounds
Charming 110-year former Inn 10' from the Ocean!
9.8 out of 10, Exceptional, (99)
"Lovely home in a beautiful location. Very welcoming, cozy, and friendly. Easy check-in and check-out process. The owner was very accommodating and helpful. Made amazing memories and look forward to returning soon. Thank you so much!"
Charming 110-year former Inn 10' from the Ocean!
On the beach
Gorgeous ocean-front home with stunning beach views
9.6 out of 10, Exceptional, (74)
"Great little condo. Right on the beach! Balcony is wonderful, as is the view from the master. Second bedroom is definitely a “kids” room with the two bunk beds. Garage was great for a car, would not fit the height of a truck"
Gorgeous ocean-front home with stunning beach views
Property grounds
Bliss Beach House ♦ Huge Ocean View Rooftop Deck ♦
9.6 out of 10, Exceptional, (10)
"This place is just as nice as it looks in the pictures! My friends and I had a blast! What we appreciated the most was how communicative Jason was with us, and how welcome he made us feel! 10/10 recommend. Awesome place! :)"
The price is €634
per night
20 May - 21 May
Bliss Beach House ♦ Huge Ocean View Rooftop Deck ♦
Private kitchen
Elegant condo - walk to Portland's best restaurants & Old Port
9.4 out of 10, Exceptional, (45)
"The kitchen was very well equipped. Living room was so cozy with the fire. Bed was super comfortable. The unit has really tall ceilings and is cozy. Only issue was the dog upstairs. They kept barking and whining."
The price is €403
per night
12 May - 13 May
Elegant condo - walk to Portland's best restaurants & Old Port
Private kitchen
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
9.4 out of 10, Exceptional, (21)
"Stayed for a weekend for bachelorette party! Very clean, close to downtown and loved the hot tub."
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
Property grounds
100 feet from the ocean 3 bedroom cottage 420 friendly
9.2 out of 10, Wonderful, (13)
"The property was great and a very convenient location to the beach, shops, and pier. They have everything you could possibly need except food and clothing! Very clean, TVs and ACs in every room. The only challenge as others mentioned is parking. It is a tight fit and if your tires are on the sidewalk you can be ticketed. On our second to last day we were approached by the parking patrol and told this. He was super nice and said he wouldn't ticket us but another may. I said we were leaving the...
100 feet from the ocean 3 bedroom cottage 420 friendly
Exterior
Large 2BD cottage 10 min to Pier & Beach Pets ok
9.2 out of 10, Wonderful, (15)
"The house was cozy and well equipped. We had a wonderful time."
The price is €207
per night
13 May - 14 May
Large 2BD cottage 10 min to Pier & Beach Pets ok
Beach/ocean view
Oceanfront Condo! Spectacular Views From Private Large Balcony
9.0 out of 10, Wonderful, (112)
"A good room/property. Check in & out was easy. Beds were a little firm, but everything else was good."
The price is €452
per night
10 May - 11 May
Oceanfront Condo! Spectacular Views From Private Large Balcony
Beach
East Grand Ave Fabulous Cottage
9.0 out of 10, Wonderful, (110)
"Good location, owner was very responsive to our needs."
East Grand Ave Fabulous Cottage
Beach nearby, beach towels
Come enjoy 7 miles of beaches in Sunny OOB in this 2 bedroom condo.
9.0 out of 10, Wonderful, (47)
"Cute little place, perfect for a night away after college graduation. 2nd Bedroom was very cramped for adults, fine for kids. could use a few more touches but otherwise would recommend. Great that it had 2 parking spots"
The price is €298
per night
10 May - 11 May
Come enjoy 7 miles of beaches in Sunny OOB in this 2 bedroom condo.
Beach nearby
2 min walk to the beach. Pet friendly condo
9.0 out of 10, Wonderful, (21)
"such a cute little place. We enjoyed staying here across from the beach so it was quick access."
The price is €208
per night
14 May - 15 May
2 min walk to the beach. Pet friendly condo
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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.

Other types of properties in Portland you may be interested in

Bar (on property)
Canopy by Hilton Portland Waterfront
4.0 star property
9.4 out of 10, Exceptional, (640)
"Very nice place"
The price is €215
per night
12 May - 13 May
Canopy by Hilton Portland Waterfront
Honeymoon Suite, 1 King Bed
Portland Harbor Hotel
4.0 star property
9.0 out of 10, Wonderful, (1187)
"Our first time staying at this property - will not be our last! "
The price is €199
per night
27 May - 28 May
Portland Harbor Hotel
Water view
The Westin Portland Harborview
4.0 star property
8.6 out of 10, Excellent, (1058)
"Staff was very friendly and made my stay better ."
The price is €173
per night
13 May - 14 May
The Westin Portland Harborview
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.

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, apart-hotels, 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 €207 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 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 fascinating museums 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?

Rent a room in the gorgeous Holt House: This highly rated holiday home rental in Portland has 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 117 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 Wadsworth-Longfellow House. 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.

Recent reviews of Portland properties
Expedia verified reviews

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

5/5 Excellent
"This hotel is located in a very convenient location in downtown. "
A verified traveller from Belmont stayed at Portland Regency Hotel & Spa
Posted 15 hours ago
Portland Regency Hotel & Spa