Holiday Rentals in Portland

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Holiday Rentals in Portland

The Weldon Hotel

4.0 star property
9.6 out of 10, Exceptional, (44)
"Literally my favorite hotel in Portland, I can’t believe I’m just learning about it. "
The price is €154
includes taxes & fees
23 Mar - 24 Mar
The Weldon Hotel

The Globe House on Munjoy Hill - Walk to Breweries

10.0 out of 10, Exceptional, (75)
"Just as advertised. Fun and happy space. Incredibly well located. Would return in an instant."
The Globe House on Munjoy Hill - Walk to Breweries

Adorable Portland getaway on the Eastern Promenade

9.8 out of 10, Exceptional, (93)
"Perfect location. Wonderful accommodations"
The price is €177
includes taxes & fees
19 Mar - 20 Mar
Adorable Portland getaway on the Eastern Promenade

Cozy, Elegant and Bright 2 bed in the East End

9.8 out of 10, Exceptional, (36)
"Very clean. Nice walk along bikepath to downtown. Will look to stay here again. Loved the neighborhood and parking was easy. Kitchen had everything we needed to cook. "
The price is €344
includes taxes & fees
19 Mar - 20 Mar
Cozy, Elegant and Bright 2 bed in the East End

Rent a room in the gorgeous Holt House

8.0 out of 10, Very good, (14)
"Really cool room and in a great location only a short walk from restaurants and sights. "
Rent a room in the gorgeous Holt House

Glorious getaway on Portland's Eastern Promenade.

10.0 out of 10, Exceptional, (145)
"Old friends (in age and longevity of relationships) met up in Portland for a weekend getaway. Great location. Great city. Enjoyed our time exploring the city culture and restaurants within easy reach but also spent long hours in the bright living room catching up over a pit of tea."
The price is €237
includes taxes & fees
16 Mar - 17 Mar
Glorious getaway on Portland's Eastern Promenade.

City Amenities, Casco Bay Sunrises and Natural Beauty

9.8 out of 10, Exceptional, (100)
"Just a few days to relax and see a new area of Maine. Our place had terrific decor, very clean, great location to get to everything in the area. Mat was very receptive to any questions and very accommodating. "
The price is €269
includes taxes & fees
13 Mar - 14 Mar
City Amenities, Casco Bay Sunrises and Natural Beauty

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

9.4 out of 10, Exceptional, (60)
"Great layout, well-appointed and super walkable to Old Port, the great restos on Washington and the Eastern Promenade. Only downside was communication with Vacasa: they always answered but didn’t necessarily address the issue, ie I struggled with the electronic door lock, was leaving for the weekend, they said the owner would come address it but when I returned 3 days later it had been left unlocked all weekend. Unreliable WiFi & I work remotely. Several times had to work from cafes.beautifully...
The price is €389
includes taxes & fees
13 Mar - 14 Mar
Elegant condo - walk to Portland's best restaurants & Old Port

Prime City Living Townhouse by RedAwning

2.0 star property
8.0 out of 10, Very good, (1)
"It was very convenient. "
The price is €475
includes taxes & fees
13 Mar - 14 Mar
Prime City Living Townhouse by RedAwning

Incredible Location! Heart of Old Port|Roomy Condo

10.0 out of 10, Exceptional, (26)
"Literally the MOST perfect location to stay in Portland. Everything was beautiful, clean, comfortable, and right in the heart of Old Port. We wish we could rent here haha! "
Incredible Location! Heart of Old Port|Roomy Condo

Stunning and Spacious 6 BR Waterfront House with Hot Tub

10.0 out of 10, Exceptional, (53)
"We had an awesome family weekend staying here! We had 8 adults and 3 kids stay. House is set up like a multi family home with a 2 bed/1 bath apartment upstairs away from the main central space downstairs (with small kitchen and a living room with TV included in apartment). We spent most of our time on the main level which has the open living room/ dining room / side room area with the trundle bed. There is a large bedroom on this floor as well and the trundle room has doors to close it off as a...
The price is €1,156
includes taxes & fees
13 Mar - 14 Mar
Stunning and Spacious 6 BR Waterfront House with Hot Tub

Luxury Condo Downtown Portland Old Port

9.4 out of 10, Exceptional, (15)
"Loved the the location. Really nice shower. Super easy check and check out. "
Luxury Condo Downtown Portland Old Port

Gorgeous ocean-front home with stunning beach views

9.6 out of 10, Exceptional, (101)
"We stayed to visit family in the area. The location was excellent and we loved the ocean view. Everything was very clean, except under the sofa in the living room. We searched for a dropped puzzle piece and "
Gorgeous ocean-front home with stunning beach views

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 €213
includes taxes & fees
13 Mar - 14 Mar
Oceanfront Condo! Spectacular Views From Private Large Balcony

100 feet from the ocean 3 bedroom cottage 420 friendly

8.6 out of 10, Excellent, (16)
"Owner should get new cleaners. House smelled like dog urine. Bathroom smelled like human urine. Had to clean floors and bathroom…lots of dirt…not sure the last time floors were I’m mopped. Dog hair on sheets. Beds were not comfortable so be prepared. Parking is a challenge. One paid parking spot in front ($36/day). Can park super close to house for 2nd spot. Owner not very responsive. Had to constantly message for arrival info and didn’t get it until 10 mins after checkin time. No instructions...
100 feet from the ocean 3 bedroom cottage 420 friendly

Large 2BD cottage 10 min to Pier & Beach Pets ok

9.4 out of 10, Exceptional, (26)
"This 2 bedroom cottage was perfect for our 3 day stay.Location was a 10 minute walk to the boardwalk.Would like to come back in the summer."
The price is €201
includes taxes & fees
17 Mar - 18 Mar
Large 2BD cottage 10 min to Pier & Beach Pets ok

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

9.8 out of 10, Exceptional, (199)
"This is exactly what we needed to do a "wow what a crazy life we have" reset. Beautiful view for sure. And the deck was warm in the winter sun."
The price is €323
includes taxes & fees
13 Mar - 14 Mar
Oceanfront condo!!!! Steps to 7 mile beach & downtown OOB. 3rd floor w/elevator

Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!

8.2 out of 10, Very good, (50)
"We had a large group and had more than enough beds and plenty of space to hang out. Would recommend for a big group or a family looking to spread out!"
Cozy & Secluded Estate on 7 acres, Boasting Fresh Renovations!

Quintessential Maine Beach Cottage

10.0 out of 10, Exceptional, (106)
"Loved our stay on the edge of the marsh! The house is adorable and well equipped. An ice storm the day prior to our arrival made pretty much every walkway in Maine (and in the driveway and walkaway to the house) an ice skating rink, but we managed not to break any hips. So peaceful watching the ice flows and ducks traveling down the marsh creek. The shells on Goose Rock Beach were plentiful and the seals that watched (laughed at?) us from afar as we prepped for a polar plunge (we chickened out...
Quintessential Maine Beach Cottage

Beach House ∆ Prime Location ∆ Steps to the Ocean

10.0 out of 10, Exceptional, (40)
"Great place.... Very clean and everything you will need to stay. It was three levels and it had supplies needed for the beach (Beach wagon, chairs, towel, sand toys...). We stayed off season so most of the houses were vacant. We would definately come back again. I did send two messages to the owner, but did not get a response. "
The price is €467
includes taxes & fees
14 Mar - 15 Mar
Beach House ∆ Prime Location ∆ Steps to the Ocean
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

Ramada Plaza by Wyndham Portland

3.0 star property
7.6 out of 10, Good, (1035)
"They had 2 hot tubs, wish the pool was warmer but it was clean. Staff was great. "
The price is €92
includes taxes & fees
23 Mar - 24 Mar
Ramada Plaza by Wyndham Portland

Portland Harbor Hotel

4.0 star property
9.2 out of 10, Wonderful, (1461)
"Always wonderful! Ana helped us find an open conference room so my colleague and I could work together. "
The price is €166
includes taxes & fees
26 Mar - 27 Mar
Portland Harbor Hotel

La Quinta Inn & Suites by Wyndham Portland

2.5 star property
9.0 out of 10, Wonderful, (2093)
"Staff are excellent "
The price is €82
includes taxes & fees
13 Mar - 14 Mar
La Quinta Inn & Suites by Wyndham Portland
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 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?

The Globe House on Munjoy Hill - Walk to Breweries: This highly rated holiday home rental in Portland is located in the city centre, and has a garden, a selection of games and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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, 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.