Waterfront holiday rentals in Cumberland

The apartment is beautifully designed, spacious, relaxing, and comfortable. What more could you ask for? We enjoyed our 3-night stay. Read some of the assembled books on birds and enjoyed delicious food at the local restaurants. Alice was a gracious and responsive host. You will truly love staying in her apartment!

it's a magical location and such a well appointed apartment. as someone who has hosted on airbnb, I really appreciated all the amenities they had. the hosts are so dope as well. you cannot go wrong with the place, the location, or the vibe.

The Crow's Nest was a lovely apartment with a great view of the city from the rooftop. The photos and description of the apartment matched the actual experience. Kathy was super responsive any time we reached out to her. She also gave us a fabulous list of recommendations for the area including restaurants, coffee shops, bakeries, and local hikes.

The location is incredible! Ive never had such a great view. The place was clean and comfortable. Booth ay Harbor is very nice place to stay.

We really enjoyed Suzanne’s charming apartment. It had everything that we needed and a lovely porch off the kitchen overlooking the river. Great coffee shop next door! Nonna’s Italian restaurant and Big Day brewery are excellent. There is a cool art shop across the street from Nonna’s

Adorable, idyllic, comfortable, serene. Couldn’t have asked for a better spot for our Maine Minimoon! Some places have 5 stars and aren’t really legit — this is not one such place. Hillary’s place fully deserves ⭐️⭐️⭐️⭐️⭐️. We look forward to staying again soon!!

These accommodations were perfect! Overlooking the Casco Bay harbor, the view was even better than depicted in the pictures. The condo was meticulously clean and very well appointed. The beds and pillows were so comfortable we slept even better than we do at home. The location could NOT have been better! It overlooks Portland’s old-town shopping district, and is easily walkable to all of the best restaurants in town. There is a beautiful walking trail just up the street, and you can easily catch the ferry to the islands from this location. It is convenient, beautiful and welcoming.

I can’t say enough about this cute condo right on the water! Easy to find and close to restaurants and historic sites, plus cute shops and art galleries. Audray was an amazing host and we will certainly be back!

Stayed at Bethany's place for a long weekend at the end of the season. The location is unbeatable, the house is situated on its own little peninsula in a stunning cove; it feels very private and has amazing views of the water. There's tons of outdoor space and seating, along with several kayaks. The house itself is clean, quiet, and peaceful, although it's definitely small--probably best for one or two people, or a couple with a small child. Access is down an unpaved road but Bethany's very clear instructions made it easy to find, and she was responsive to any questions we had. Harpswell abounds with areas to hike and explore, lots of good places to eat (though you will definitely need a car) and is less than an hour from Portland and only half an hour from Freeport.

We had a wonderful stay at this beautiful beachfront home with our extended family, including a total of 6 adults and 5 kids. We had two additional adults spend one night, there was plenty of room for everyone. The house was spacious, comfortable, and perfectly suited for a group of our size. The location is unbeatable, right on Drakes Island Beach, with incredible views and direct access to the sand. While we didn’t go in the water, we spent plenty of time relaxing on the beach, walking along the shore, and enjoying the peaceful setting. The home was clean, well-maintained, and stocked with everything we needed. The large deck and open living spaces gave us plenty of room to spend time together and unwind. This was a perfect spot for a relaxing family getaway, and we’d absolutely return again. Highly recommended!

Enjoyed our stay very much! Lovely location on the water. Some white traffic noise but worth it watching the boats and wildlife! Comfy bed. We slept very well. Well-stocked kitchen. The location is perfect for lots of little day trips. Our only disappointment was the size of the smallest room. It’s very tiny. Great for a child but pretty tight for our adult son. Host was attentive. We will be back!

Perfect weekend retreat for a small family with a young one. Close to downtown, museum, and the firepit was so nice at night. 5 stars all around and will return in the future. Thanks Phillip!

Beautiful, well-appointed home. All the little things add up to a stress-free experience. Fully stocked with towels, cooking supplies, even q-tips if you forget your own! By far the cleanest, most comfortable AirBNB I've stayed in. Photos don't do justice to the view from inside and from the patio. Incredibly quiet at night and the feeling of seclusion helped recharge my batteries. Super clear directions and entry instructions. Nothing beats dinner or wine by the firepit overlooking the bay except for the sunrise over the water. Would 100% stay again.

We loved our stay (late May, 2025). The weather did not cooperate but the house was perfect. Thank you Debbi!

I can’t say enough about what a nicely appointed home in a beautiful setting this is. I came for peace and tranquility and it did not disappoint. I haven’t had such good sleep in over 2 years. Highly recommend and plan to return next year! Thank you all so much for sharing your lovely home.

fantastic stay. clean and well equipped. the lake is even more beautiful than the pictures! Roman was very responsive and went above and beyond in providing helpful information about the area and place.

Unit was very clean, situated in a quiet residential area and within walking distance to many of Portland's best bars, restaurants and attractions. Host was communicative and provided clear guidance on check-in/-out procedures and offered up suggestions to local attractions. On my recommended list - dinner at Twelve (one of the best restaurants in the US, IMHO); on-site food truck tacos washed down with a Hazy IPA at Bellflower or Austin Street Brewery; an everything bagel with lox & morning latte at Forage; the East Promenade for a food truck lunch, then a stroll along the waterfront trail to the port area for an ice cream cone at Gorgeous gelato; afternoon coffee at Double Great Coffee; and a post-dinner whiskey @ Independence Ice. Only downside on my visit was the upstairs neighbor. Dude clearly isn't a principal dancer in the Portland Ballet, as light on his feet wouldn't describe him. Not a stereo or TV issue - you can just hear the noise from him walking (8AM-10PM when there)

Wonderful place, beautiful view, clean home, would Definitely rebooked in the near future! 100% recommend

Deborah was very helpful and quick to respond. She had great suggestions on where and what to visit. The travel magazines she had on her TV stand were extremely helpful. The bed was very soft, which I love, so I slept really well. We loved the touch of having beach chairs available. The only downsides I can think of, are that the shower is very small, and it’s hard to back out of the parking space.

This AirBnB was a perfect winter vacation escape. It had everything we needed for our two families. The kitchen was so well stocked and we were never without. Great set up. My 5 year old begged to live there forever! We can't wait to come back!

Great stay

Christopher was a helpful host and his place was perfect! Clean, fully stocked, great location. It was close to lots of beaches and restaurants and the pool was great for the little ones

This cute little cottage was perfect for my stay in Old Orchard Beach. My stay was in cold January but the cottage was warm and cozy. The highlight was being steps from the beach and being able to roll out of bed and catch the sunrise each morning.

Perfect little place for a weekend away near Portland!