
Condo holiday rentals in Cumberland
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Top-rated condo rentals in Cumberland
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Endless Direct Beachfront Views! 2 Oversized Decks
Such a lovely stay! The view of the beach was absolutely beautiful, and the location was perfect—just a short walk to local stores and great restaurants. The space was very clean, cozy, and ideal for a mix of relaxing and fun weekend getaway. Highly recommend!

Charming, newly remodeled space atop Munjoy Hill.
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)

Stunning Mt Washington Views
Tim's place was great! Felt like home. View is amazing! Cathedral wood ceilings make the place so warm and cozy. Kitchen and bathroom clean with upgrades. Comfortable beds and spacious rooms. Location is perfect. Close to restaurants, N. Conway, and both Crawford and Pinkham notch for hiking and other adventures. Tim was super responsive and friendly. Would definitely rent again!

2-Bedroom Condo Close to Downtown
What a great location for a quiet stay in Portland! It’s 5 minutes by car to the Old Port and easily walkable/runnable to the Back Cove Trail and even to downtown Portland itself. The condo is lovely and just as described. My family (2 adults, 2 kids ages 3 and 7) was very comfortable during our 3-night stay. Lastly, Colin was responsive and a great host.

Cozy Family Retreat with Saco River Access
Our 3rd time staying here....great location and reasonably priced. Love the view out back to the trees and a peek of some mountains. Also great snow cleanup - we were here for a big storm and the plows cleared the car park and the paths were shoveled quickly.

Cozy studio-5 minute walk to Perkins Cove!
Great place to stay, Ogunquit is such an endearing place to be 😄

Boho Surf Studio: Steps from the Beach in OOB!
Was the perfect place for a little mental retreat, was exactly the place I needed to be to clear my head and escape reality for the week I spent there. The host Amie was so helpful with questions about the area and able to give recommendations on local restaurants and parking for visitors. All in all I had an amazing time here and will definitely be booking again.

Summit Vista | Paradise | Hike • Ski • Story Land
Awesome location for a Storyland weekend. Unbelievable sunsets, beautiful views, comfortable beds, perfect layout for a group. Can’t wait to come back!
Pet-friendly condo rentals

My Old Port Sanctuary - Lux by the water & dining
Great location. Everything within walking distance. Very clean. Comfortable beds. Great water pressure in the shower. Well equipped kitchen. Feels like a very safe area and has a free parking spot. Would absolutely stay here again.

Charming 2-Bedroom Back Cove Retreat
This home was just perfect for a few days of R&R for my sister and me. The apartment is perfectly appointed with everything needed for a relaxing and easy stay. Kudos to the designer - the space was the perfect blend of a lovely aesthetic and function. I will certainly be remembering this little gem for the next time I'm in Portland!

Over 1000 Five Star Reviews! Walk to Dock Square !
Great location (definitely check out Pedro’s across the street). The place was clean and well stocked with necessities. Beds were comfortable, pillows were good, curtains would have been nice due to the early sunrises.

River Escape - Studio Apt. with River Access
Lovely stay in a cozy place during a harrowing move. Cozy place provided just what we needed.

Walk Everywhere | Free Parking | DogsOK | King Bed
Nick and Kyla’s place was wonderful. It was perfect for our group. It looked exactly like the photos, and it was very clean. The location was perfect for getting around the Portland area with many things right in walking distance. Our hosts were very friendly and responsive, and their instructions were clear. I would definitely recommend staying with them to others.

Luxurious 2BR Penthouse | Ocean Views | East End
Wonderful—everything about this place. I loved it and will stay again one day. Fantastic.

Downtown Old Orchard beach 1 bedroom
Amazing location. Very close to the beach. Perfect room! We enjoyed our stay at Mary’s place!

Renovated quiet unit, pet friendly
We came during the off season and had a quick two day stay here and thought it was great for us and our two small dogs.
Condo rentals with a pool

Upscale retreat w/ panoramic White Mountain views
We really enjoyed our stay at Lisa’s house in our white mountains foliage trip. Very quiet and stunning views of the mountains in color right in the living room. Secluded location but very short drive to Jackson and Conway. We would be happy to return again. Highly recommended!

Cozy Beach Condo in Wells - Hot Tub & Pool!
Kathleen’s Ogunquit Airbnb is perfect! She has thought of everything you may need and more. Kathleen was responsive when needed and communicated helpful details throughout our stay. The location is fantastic and made exploring the Maine coastline very convenient. Thank you, Kathleen!!!

Don’t miss out, book for Fall NOW!
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!

Two-Bedroom Condo on the Wells/Ogunquit town-line
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

Starfish Condo Wells Beach
This was a great find and enjoyed our 3 week there - We got to meet a few neighbors, and they were very nice as well - Very close to restaurants and Wells Beach - WIFI worked great as I work from home and the tip about leaving the second car at the Wells Transportation Center helped a lot ! Danielle was great with communication and rules - We would stay here again

Relaxing Beachside Condo with Pool at Wells Beach
Julie’s place was very nice and very clean. The location was great, right across the street from the ocean. The kitchen was well-equipped and there was even a small basket of treats. Julie responded very quickly to any messages we sent. We would highly recommend this place.

3 bd / 2 bth, SLOPE SIDE at Cranmore! Unit#1104
Jennifer's place is AMAZING! First, it's steps away from the ski lift. Not only can you make first tracks, but stopping for lunch/breaks/warm-up is super easy - ski to your door! Getting in was a breeze: pull up, get the FOB, grab a luggage rack and park in the designated spot by the door and you're done. No long walks hauling ski gear through endless parking lots. The condo is spacious, super comfortable, and great for hanging out. We had 4 adults and 4 kids (8-11) and we had plenty of room for game nights, dinners, and lounging after a long ski day. The bathrooms are big (and even a jet tub for bubble baths). And immaculately clean. Full kitchen equipped with everything you need. So great to have washer/dryer to get gear ready for the next day. And the heated pool/hot tub is a short walk, both are big and a hit with the kids and adults. And did I mention how clean the place was? The unit is on the end to give extra privacy and easy access. Six stars!

Cozy, clean, 2nd floor condo in Conway, NH!
A beautiful condo, just 20 minutes away from the heart of North Conway. Everything was in pristine condition and it is always amazing to have a kitchen at our fingertips. Beautiful views of the woods out back. Would definitely recommend to those coming to visit the North Conway, New Hampshire area and surroundings!!!!
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- Ogunquit Beach
- Sebago Lake
- Wells Beach
- Scarborough Beach
- York Harbor Beach
- Long Beach
- Popham Beach State Park
- Surfside Beach
- Long Sands Beach
- Pemaquid Beach
- Brunswick Golf Club
- Fox Ridge Golf Club
- Coastal Maine Botanical Gardens
- East End Beach
- Cranmore Mountain Resort
- Palace Playland
- Ferry Beach
- Cliff House Beach
- Pemaquid Point Lighthouse
- King Pine Ski Area
- Purity Spring Resort
- Diana's Baths
- Ogunquit Playhouse
- Dunegrass Golf Club