
Holiday rentals with outdoor seating in Cumberland
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Top-rated Holiday Houses with Outdoor Seating in Cumberland
Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.
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Popular amenities for Cumberland outdoor seating rentals
Holiday House Rentals with Outdoor Seating

Reno Barn w/ a lot of Charm! Breweries & Airport
Fantastic place to stay with comfy beds and a great location! Would definitely recommend!

Kelley's Ocean View Cottage
Our son, his girlfriend, my husband and I enjoyed staying at the cottage in late October 2024. The location was quite scenic as it overlooked Casco Bay, near Portland, ME. The host made suggestions that we followed (bringing firewood & blankets). The kitchen was equipped with utensils & coffeemakers. The neighborhood was quiet. We enjoyed walking in the local preserve along the water and took advantage of visiting the Portland Museum of Art and eating at The Honey Paw, an Asian fusion restaurant.

Waterfront Gem walkable to Restaurants!
a wonderful place to stay.

The Inn on Ludlow Street
Cathy’s place was wonderful for our family stay. Lots of space to hang out, everything is super clean, and Cathy provides everything you could need. She was also very gracious when we were not out by 10 AM, thinking that checkout time was 11. We would definitely stay here again and strongly recommended. Thank you, Cathy!

Hilltop Retreat with Hot Tub & Sauna near Downtown
Everything was as described and more! With a wonderful location close to town, good privacy, and so much space inside with many commodities we wouldn’t even think of. Even our dog had a fun filled week with us. We hope to visit again, it’s just the perfect home away from home. Couldn’t recommend a better place to stay.

Stone Isle. 8 acres next 2 little john preserve.
Amazing surroundings and views. The reserve loop walk is great.The perfect Maine coastal experience.

LUX Designer Private Waterfront
We came here for a private getaway on our honeymoon and it did not disappoint. The price was a bit much, but for such a special time I felt it was worth it at the time I booked, and worth it it certainly was. beautiful, quiet, serene, it was perfect for a getaway. I would absolutely recommend, and I already have, this stay. 10/10

Beautiful Home In Gorham Maine
We stayed at Rob and Nate's place while we visited Portland and the surrounding area over the long weekend. It was the perfect choice! They were great hosts. Their home was in a beautiful setting. From the back deck, we could look out onto beautiful gardens and a small pond. The home itself was lovely and cozy, spotlessly clean, and had all the amenities we needed. It was an easy drive to Portland and Sebago Lake. We would definitely recommend staying here!
Apartment rentals with outdoor seating

Cape Elizabeth Garden Apt+Beach+Close to Portland!
Enjoyed our stay so much! Nestled into a picturesque and quiet town. Super easy to get to and from Portland without having to stay in the hustle and bustle of staying directly downtown. The house itself is charming and clean. Felt like we were coming back to our own home every night after exploring Portland and the surrounding cities. Plus, the banana bread was such a sweet and thoughtful touch. 10/10 would recommend to anyone!

Clean & Safe Apt w/Parking-Close to Downtown
Great little place. We parked our car and trailer right in front of the house, had takeout and a few groceries delivered (I think we used DoorDash or GrubHub), and got rested up for the next leg of our trip. Hyeri was super kind and responsive.

Sauna & fire table near Portland's Back Cove
Arian’s house is so lovely. It’s cozy, modern and very clean. The house is in an excellent location close to restaurants and walking paths. Arian was responsive and helpful. We highly recommend his place if you’re looking for somewhere to stay in Portland

Elegantly Done Apartment in a Sun-Drenched Corner Lot House
The apartment was very comfortable. We would definitely stay there again if we’re ever back in Portland.

Oceanside Modern Victorian 2BR- East End/ Downtown
Great stay! Location is perfect for everything we wanted to do, be by the water, stay right next to downtown, and a short walk from our tour with Eco Adventures. Furniture was very comfortable and everything was clean. Great restaurants in the area. Would return back!

Adorable getaway on the Eastern Promenade
A lovely place to stay in Portland’s East End. Great location in a very quiet and walkable neighborhood. (I happily did not need a car during my visit.) The apartment is great, with a comfy bed, smart TV and a nice little patio too. And you’re just steps from the Eastern Promenade park, which is one of Portland’s best amenities imo and leads to a beach, waterfront trail, dock w/ kayak rentals, etc. Jennifer was a very kind host; thank you!

The Yankee Dugout
This place was perfect for our quick weekend getaway. Super clean, clear instructions, and great location. Barry was super responsive and helpful with everything we needed. Would definitely recommend!

Hip & Cozy, high end Modern Design
Kate’s place was cozy and clean with lots of added amenities. It was in a great location to explore the town and easily walk to places if you wanted! Definitely would recommend to family and friends!
Condo rentals with outdoor seating

Oceanfront Condo with Awesome Views
Great stay

Modern Industrial Beach Cottage
Very nice stay! The location is perfect, everything you need is on site. I recommend it!

Cozy condo with North Conway at your finger tips!
We had a great time! The place was very clean, nicely maintained, and in a perfect location—just a short drive to local coffee shops and great restaurants. The surrounding nature was absolutely beautiful and made the whole trip feel relaxing and refreshing. Highly recommend!

Cozy condo by the beach!
Wonderful little spot very close to the beach. Plenty of places to walk to from the location as well as a short drive to Old Orchard Beach. Would come back in a heartbeat!

Top Of The Line Stay!
Great place to stay if you want to be close to downtown but with a larger, comfortable space. The place is exactly as described, exceptionally clean and tastefully decorated. No dollar store products here! The ground coffee and half and half really made it feel like we were staying at a friend’s home.

Attractive 1 bedroom cabin only 50 ft from beach#1
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.

Comfy condo with loft by the beach!
We had a great time! The condo is clean, cozy, and comfortable. I highly recommend this AirBnB, especially for the beach proximity.

Rustic Willard Beach condo ten mins from Old Port!
We loved our stay! The space is beautiful and cozy. The walk to the family friendly beach was just the right distance for my 4yo. The neighborhood is adorable and friendly! With an amazing bakery and ice cream shop just around the corner! Dave was a great host and took great care of us.
Quick stats about holiday rentals with outdoor seating in Cumberland
Total rentals
90 properties
Nightly prices starting at
$99 NZD before taxes and fees
Total number of reviews
5.1K reviews
Family-friendly rentals
60 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
50 properties have a dedicated workspace
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- Ogunquit Beach
- Sebago Lake
- Wells Beach
- Scarborough Beach
- York Harbor Beach
- Popham Beach State Park
- Long Beach
- Surfside Beach
- Long Sands Beach
- Pemaquid Beach
- Diana's Baths
- Fox Ridge Golf Club
- Coastal Maine Botanical Gardens
- East End Beach
- Cliff House Beach
- Brunswick Golf Club
- Palace Playland
- Pemaquid Point Lighthouse
- Ferry Beach
- Funtown Splashtown USA
- Cranmore Mountain Resort
- Purity Spring Resort
- King Pine Ski Area
- Dunegrass Golf Club