Holiday Rentals in Portland

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Holiday Rentals in Portland

The Weldon Hotel

4.5 star property
9.8 out of 10, Exceptional, (81)
"Absolutely beautiful place to stay. "
The price is €339
includes taxes & fees
28 Oct - 29 Oct
The Weldon Hotel

Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.

2.0 star property
10.0 out of 10, Exceptional, (4)
"Very smooth and easy check-in. Very nice room and bathroom. Thank you so much for letting us stay! "
Cozy and Quiet Home One Bedroom Private Bathroom in Portland Maine. NOT KITCHEN.

Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

10.0 out of 10, Exceptional, (64)
"We stayed for a group trip to Portland and this was the perfect spot. Location is fantastic, lots of comfortable sleeping options, and great communication from the host. Highly recommend! "
The price is €966
includes taxes & fees
6 Oct - 7 Oct
Spacious Craftsman w/ Casco Bay Views. Hot Tub, Patio, Easy Access to Old Port

Studio Unit Walkable Everywhere

5.2 out of 10, (5)
"We didn't stay there at all. Canceled reservation "
The price is €146
includes taxes & fees
19 Oct - 20 Oct
Studio Unit Walkable Everywhere

Private Entrance Residential Portland

9.2 out of 10, Wonderful, (5)
"Great location for seeing the Portland Head Lighthouse. Comfortable bed."
The price is €158
includes taxes & fees
30 Sept - 1 Oct
Private Entrance Residential Portland

Spacious Historic Home | 7BR West End for Groups

10.0 out of 10, Exceptional, (6)
"Perfect accommodation for extended family to get together for a long weekend. House was comfortable and well-appointed with plenty of space, beds, towels etc. Air conditioning worked perfectly when needed."
The price is €1,404
includes taxes & fees
8 Oct - 9 Oct
Spacious Historic Home | 7BR West End for Groups

The Cottages at Cabot Cove

3.5 star property
9.6 out of 10, Exceptional, (39)
"Amazing property. Wonderful staff, perfect cabins close to town. Breakfast delivered each morning was a treat!"
The price is €425
includes taxes & fees
30 Sept - 1 Oct
The Cottages at Cabot Cove

Sensational Beachfront Property Old Orchard Beach, with indoor elevator

9.6 out of 10, Exceptional, (64)
"Our stay was perfect. The house allowed for us to sleep 17 people comfortably, eat together, cook in teams for a progressive dinner and spread out all at the same time. Jason was quick to answer questions, and he provided excellent suggestions for places to eat and shop. We could not be more pleased with our stay. Thank you, Jason!!"
The price is €1,233
includes taxes & fees
1 Oct - 2 Oct
Sensational Beachfront Property Old Orchard Beach, with indoor elevator

68 East Grand Ave

3.0 star property
8.6 out of 10, Excellent, (9)
"Property was very nice and close to the beach. Would stay there again. The front desk was extremely helpful as well. "
68 East Grand Ave

Bright and airy condo with beachfront access and walkable entertainment nearby

7.6 out of 10, Good, (4)
"Ease of beach access. "
Bright and airy condo with beachfront access and walkable entertainment nearby

Beach House ∆ Prime Location ∆ Steps to the Ocean

10.0 out of 10, Exceptional, (48)
"We loved everything about our stay here. Perfect location right on Old Orchard Beach. The house is perfect for what we needed/wanted. Wish we could have stayed longer. We would definitely come back for a longer stay next time we’re in Maine. "
The price is €425
includes taxes & fees
8 Oct - 9 Oct
Beach House ∆ Prime Location ∆ Steps to the Ocean

Cozy Coastal Condo with Parking – Walk to Beach & Town

2.0 star property
8.2 out of 10, Very good, (14)
"The place was clean and spacious enough for our family of 4. A simple place within one block of the ocean. Can’t beat that! When we had an issue with WiFi, they responded promptly and all was rectified very quickly. Easy access upon arrival and clear directions about departure. Would recommend ."
Cozy Coastal Condo with Parking – Walk to Beach & Town

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

10.0 out of 10, Exceptional, (229)
"Beautiful views, very clean and enjoyed the oceanside vibe both inside and out! Easy walk to general store and walkable to Giant Stairs trail and Cedar Beach."
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

Private, 2nd Floor Cottage with Wonderful Ocean Views- Perfect for Families!

9.8 out of 10, Exceptional, (45)
"This place is a real gem. Really clean, well equipped and for our two kids it was perfect (toys inside and playground in the yard. The host is very kind and very quick to fulfill our needs. Thanks again!"
Private, 2nd Floor Cottage with Wonderful Ocean Views- Perfect for Families!

350 Yards to the beach. Pet friendly!

8.0 out of 10, Very good, (34)
"Clean, easy access to everything! Fantastic stay will come again! Thank you!"
350 Yards to the beach. Pet friendly!

Grand Victorian on the Beach, Summer

9.8 out of 10, Exceptional, (78)
"I would recommend this place to everyone. We had a great time."
Grand Victorian on the Beach, Summer

Historic Kennebunkport home only 0.3 miles to Dock Square

10.0 out of 10, Exceptional, (74)
"Wonderful home close to downtown. Comfortable house and great host!"
The price is €507
includes taxes & fees
30 Sept - 1 Oct
Historic Kennebunkport home only 0.3 miles to Dock Square

Spectacular Oceanfront Property Offering Bold Panoramic Views of Saco Bay !

10.0 out of 10, Exceptional, (39)
"The view is beautiful and has everything you need "
Spectacular Oceanfront Property Offering Bold Panoramic Views of Saco Bay !

Gorgeous and Unique New England Beach House: Panoramic Views of Saco Bay!

10.0 out of 10, Exceptional, (97)
"Would love to stay here again!! "
Gorgeous and Unique New England Beach House: Panoramic Views of Saco Bay!

Full sized home

9.8 out of 10, Exceptional, (42)
"The house was lovely. Very comfortable place. Within 15- 20 mins to a store or restaurants."
Full sized home
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

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, 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 €146 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. 

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 entertainment choices 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 a Smart TV 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 82 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, 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.