Holiday Rentals in Portland

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Holiday Rentals in Portland

Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
Fridge, microwave, oven, stovetop

Spacious & Sunny 4 Bedroom Close to Downtown, hot tub

9.2 out of 10, Wonderful, (30)
"We had a great time. Nate made check in/check out very easy and the location is great. Would recommend staying here!"
Spacious & Sunny 4 Bedroom Close to Downtown, hot tub
Glorious getaway on Portland's Eastern Promenade.
Property grounds

Glorious getaway on Portland's Eastern Promenade.

10.0 out of 10, Exceptional, (142)
"We had a wonderful night in Portland! We spent the afternoon shopping in Freeport and arrived at the apartment around 5. Very easy finding parking on the street and no trouble getting inside. The apartment is absolutely adorable! Between the colors and decorations, it just gives off this girly, cozy vibe. There were 4 of us and we all had room to sleep comfortably. Wish we could have stayed another night! "
The price is €235
includes taxes & fees
8 Jan - 9 Jan 2025
Glorious getaway on Portland's Eastern Promenade.
Rent a room in the gorgeous Holt House
Exterior

Rent a room in the gorgeous Holt House

8.0 out of 10, Very good, (24)
"This was a perfect place, close to everything in Portland! "
Rent a room in the gorgeous Holt House
Adorable Portland getaway on the Eastern Promenade
Interior

Adorable Portland getaway on the Eastern Promenade

9.8 out of 10, Exceptional, (92)
"We really enjoyed our stay. This little third floor walk up was a perfect place for my husband and I to explore Portland. It is homey and comfortable and spotless. If you have any issues with mobility you should look elsewhere, but that is disclosed in the listing. The last set of stairs are very steep, but we found it charming. I highly recommend this rental. Well done! "
The price is €184
includes taxes & fees
8 Jan - 9 Jan 2025
Adorable Portland getaway on the Eastern Promenade
Elegant condo - walk to Portland's best restaurants & Old Port
Fridge, microwave, oven, stovetop

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

9.4 out of 10, Exceptional, (57)
"We really enjoyed this home and the location. The upgrades were beautiful and the restaurants nearby were amazing. When we checked out and took out our trash the outside bin had a lock on it so our only issue was not being able to access that but that wasn’t anyone’s fault. "
The price is €421
includes taxes & fees
7 Jan - 8 Jan 2025
Elegant condo - walk to Portland's best restaurants & Old Port
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
Fridge, microwave, oven, stovetop

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

9.0 out of 10, Wonderful, (28)
"Great place, a little difficulty controlling temperature."
The price is €378
includes taxes & fees
1 Jan - 2 Jan 2025
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
The Globe House on Munjoy Hill - Walk to Breweries
Fridge, microwave, oven, stovetop

The Globe House on Munjoy Hill - Walk to Breweries

10.0 out of 10, Exceptional, (74)
"The Globe House was a wonderful Plato spend a couple of days while exploring Portland. The house itself was immaculate and well appointed, with extra touches that put it a step above: the fresh scent from a diffuser welcomed us, a complimentary bottle of wine awaited us in the refrigerator, and luxe amenities like L’Occitane moisturizer were provided. Great location with easily walkable and excellent restaurants. Our hosts left a fabulous “guide to Portland” for us, with many of their favorite...
The Globe House on Munjoy Hill - Walk to Breweries
Inviting apartment with full kitchen, porch, convenient location, & fast WiFi
2 bedrooms, Internet, bed sheets

Inviting apartment with full kitchen, porch, convenient location, & fast WiFi

7.4 out of 10, Good, (20)
"After a bit of confusion getting into the house, we found a nice, very well lit, spacious home with lots of windows. The beds were pretty comfy. The location was great, easy walk to the state theater, easy to walk to lots of cool bars and restaurants. The harbor and that touristy area were about 20 to 25 minute walk away, which was lovely in the nice weather. Overall, it Served well, for four people wanting to explore Portland. "
Inviting apartment with full kitchen, porch, convenient location, & fast WiFi
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
Interior

1200 sq ft ♦ West End Townhouse ♦ Perfect Location

8.6 out of 10, Excellent, (55)
"The property is an older triplex, interior is nice. Neighborhood is quiet. Close to historic wharf area. Easy to walk to local restaurants and sites. I had my dog with me and appreciated the back yard. Of note, there is no washer/dryer in the unit. No dishwasher, but this wasn't a problem. Parking is limited to on-street and would be an issue if more than one car required space. The only bathroom and both bedrooms are on the second floor and might be a consideration for anyone with mobility...
The price is €254
includes taxes & fees
5 Jan - 6 Jan 2025
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
Gorgeous ocean-front home with stunning beach views
On the beach

Gorgeous ocean-front home with stunning beach views

9.6 out of 10, Exceptional, (100)
"The view and location are amazing. The house was very comfortable for the three adults on our trip. It’s also very suitable for a family with kids as one of the rooms has two bunk bed sets. It’s comfortable, cozy, and completely relaxing. Within walking distance of the pier and entertainment. Great place to stay. "
Gorgeous ocean-front home with stunning beach views
Quintessential Maine Beach Cottage
Property grounds

Quintessential Maine Beach Cottage

10.0 out of 10, Exceptional, (105)
"Great spot, the dog loved it too"
Quintessential Maine Beach Cottage
Beach House ∆ Prime Location ∆ Steps to the Ocean
3 bedrooms, desk, iron/ironing board, free WiFi

Beach House ∆ Prime Location ∆ Steps to the Ocean

10.0 out of 10, Exceptional, (38)
"The house is very clean, and it is only a minute walk to the beach. This was the second time we’ve stayed in this house and it won’t be the last! "
The price is €485
includes taxes & fees
8 Jan - 9 Jan 2025
Beach House ∆ Prime Location ∆ Steps to the Ocean
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
Interior

Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator

9.8 out of 10, Exceptional, (196)
"My family had a wonderful stay at your condo. They had unbelievably nice weather and got to enjoy your deck and views in early Nov. "
The price is €334
includes taxes & fees
8 Jan - 9 Jan 2025
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
Terrace/patio

PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room

10.0 out of 10, Exceptional, (99)
"This property is stunning, and the view is spectacular. If this were my house, I’d never leave! We had a fabulous time. "
PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room
Come enjoy 7 miles of beaches in sunny OOB in this 2 bedroom condo.
Beach nearby, beach towels

Come enjoy 7 miles of beaches in sunny OOB in this 2 bedroom condo.

7.4 out of 10, Good, (26)
"The location was amazing! Walking distance to the pier, and right by the beach! We enjoyed that it was far enough down from the pier that the beach was a bit less crowded but we were still able to walk downtown. The accommodations are very cute and rustic. Some things could use attention, like paint touch ups and the patio table needs replacing… however these were minor issues and we will be back! "
Come enjoy 7 miles of beaches in sunny OOB in this 2 bedroom condo.
Beachfront Luxury Grand Victorian Condo (Primetime View directly down the pier)
Third-party on-site parking

Beachfront Luxury Grand Victorian Condo (Primetime View directly down the pier)

9.8 out of 10, Exceptional, (119)
"Clean, comfortable and quiet! Beautiful views of ocean."
Beachfront Luxury Grand Victorian Condo (Primetime View directly down the pier)
Oceanfront Condo! Spectacular Views From Private Large Balcony
On the beach

Oceanfront Condo! Spectacular Views From Private Large Balcony

9.0 out of 10, Wonderful, (124)
"Great location! If you are looking for quiet time during the evening hours this isn’t the place for you as The Brunswick restaurant is directly below. If you like music and a great view, it’s an amazing spot! "
The price is €264
includes taxes & fees
8 Jan - 9 Jan 2025
Oceanfront Condo! Spectacular Views From Private Large Balcony
Little Miss Cottages
Property grounds

Little Miss Cottages

2.5 star property
8.4 out of 10, Very good, (82)
"We stayed because they accept pets. Good place the 24/7 laundry was useable but not everything working"
Little Miss Cottages
Charming 110-year former Inn 10' from the Ocean!
Property grounds

Charming 110-year former Inn 10' from the Ocean!

9.8 out of 10, Exceptional, (114)
"This location is EVERYTHING!!! Right on the beach, cozy accommodations with spacious bedrooms was perfect for the 4 of us - with the 3rd bedroom, we could've included another couple! Host John was lovely!!!"
Charming 110-year former Inn 10' from the Ocean!
Cottages by the Sea #1 | Private Beach | Steps to Sand | Bayley Vacation Rentals
On the beach

Cottages by the Sea #1 | Private Beach | Steps to Sand | Bayley Vacation Rentals

10.0 out of 10, Exceptional, (6)
"We had a wonderful stay - myself, my husband and my 6,4, and 2 year old children all enjoyed our time at the beach. We could have done without the harassment of the old lady from cottage 4 (owner perhaps?) telling us to get out at 10am. We were packing the car at 10:02 and trying to get the kids in - we were not in the cottage anymore everything was out. We left the property 10:11am. Her nagging and threats of charging extra were completely unnecessary. It was too bad to have to leave on...
Cottages by the Sea #1 | Private Beach | Steps to Sand | Bayley Vacation Rentals
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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Other types of properties in Portland you may be interested in

The Westin Portland Harborview
View from room

The Westin Portland Harborview

4.0 star property
8.8 out of 10, Excellent, (1006)
"Very nice stay, staff very friendly "
The price is €106
includes taxes & fees
20 Jan - 21 Jan 2025
The Westin Portland Harborview
Ramada Plaza by Wyndham Portland
Exterior

Ramada Plaza by Wyndham Portland

3.0 star property
7.6 out of 10, Good, (1015)
"The property was excellent. The only issue was the shower in the room. Also the vending machines were a bit tricky to operate. The staff was excellent. The room was clean and comfortable. "
The price is €99
includes taxes & fees
7 Jan - 8 Jan 2025
Ramada Plaza by Wyndham Portland
Portland Harbor Hotel
Honeymoon Suite, 1 King Bed

Portland Harbor Hotel

4.0 star property
9.2 out of 10, Wonderful, (1432)
"Amazing! clean rooms, awesome staff "
The price is €155
includes taxes & fees
2 Jan - 3 Jan 2025
Portland Harbor Hotel
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.

Frequently asked questions

Can I find a holiday rental in Portland?

Yes, there are holiday rentals in Portland close to Maine Narrow Gauge Railroad Company and Museum, 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?

Spacious & Sunny 4 Bedroom Close to Downtown, hot tub: This highly rated holiday home rental in Portland is located in the city centre, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub. Some other homes for rent in Portland include Rent a room in the gorgeous Holt House and Elegant condo - walk to Portland's best restaurants & Old Port.

How many holiday rentals are there in Portland?

Choose from 112 Expedia holiday rentals in Portland for a memorable holiday.

What can I see and do in Portland?

Maine Narrow Gauge Railroad Company and Museum 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.