
Holiday rentals with outdoor seating in Cumberland County
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Top-rated Holiday Houses with Outdoor Seating in Cumberland County
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Holiday House Rentals with Outdoor Seating

Cozy cottage near Sebago Lake
Beautiful place, everything witching driving distance

Rising Tide Times - quintessential Maine cottage
We thoroughly enjoyed our peaceful and quiet time of rest at The Rising Tides. The setting is absolutely serene. It’s very secluded and quiet, the perfect place for a week of rest and relaxation. We went hiking on the Cliff Trail (15 minutes away and a very nice hiking trail), watched the sunrise at the Lands End store on Bailey island (15-20 minutes), and kayaked in the cove. The grill was very nice and we enjoyed cooking on it regularly. The place was very clean and ready on our arrival. The host communicated very clearly. You will need to follow her driving directions as they are very clear and helpful. In our four days there we only saw 1 neighbor - and that was as we were leaving on the weekend. There’s a grocery store only 15 minutes away and we were able to stock up on our way there. Really, this was one of our favorite places we’ve ever stayed. We really enjoyed having a few options of things to do while also being able to just do nothing on our vacation in a quiet place.

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

Close to Breweries, Outlets, and Portland Food!
We booked Will’s place last minute and it turned out to be the perfect spot to relax for an evening! Nice neighborhood and close to amenities! Cute house with great Maine coastal decor. Would definitely stay again!

Kayak to the Causeway-50s cottage with modern vibe
This has been by far the nicest place we have stayed. Super clean and nicely decorated. Wonderful communication by the hosts. Perfect weekend getaway.

Dreamy Mountain Home w/ Hot Tub, Firepit, + Views!
This house was perfect for me and my guests! All 7 of us fit perfectly, It didn’t feel too overcrowded! We loved the beautiful view off the deck and the hot tub was an amazing touch! The house was very clean and had everything we could’ve needed. I loved how clear the instructions were for everything and how responsive the hosts are if you need anything!

Beautiful Coastal Maine Getaway
Stop scrolling & just book this amazing home! Randy is an excellent, gracious & very responsive host! Check-in was a breeze w/ wonderful detailed instructions for the house and region sent in advance. This house is awesome, pristine clean, beautifully decorated and outfitted. Totally turnkey set up as they thought of everything one might need to cook, relax, sleep, explore and enjoy your visit! It's very evident that these hosts want their guests to have an exceptional experience and we did! Beds were comfy along with plenty of high quality linens and supplies. We truly cannot wait to return on what will be our regular road trips to Maine! We toured Boothbay, Chebeague Island, Brunswick, Portland, Kennebunkport, Freeport and Ogunquit while we were there. Yarmouth is awesome with super friendly locals! Close by, we found Rosemont Market, Maggie Mae's Cafe and Royal River Grille convenient options among many good ones in the area. Thanks to our host for the wine & chocolate!

The "Happy Hen House" cottage in lakes region
As Mainer living across the country, it is always nice to come. Unfortunately this trip was to attend my Mom's funeral. Pam's home was the right level of closeness to the rest of my family to make visiting easy. The place was the peaceful retreat I needed to visit with myself. Five minutes to most things a person living out of a suitcase could need. Also less then 5 minutes walk puts one at the boat launch for personal watercraft. A great place to sit for a few. The amenities were plentiful at the house and the character was Maine charming. Pam was wonderful and easy to communicate with at all stages. I will be back in the future. Matt
Apartment rentals with outdoor seating

Charming 1 Bedroom Flat in the Heart of Portland
Cozy place in a nice area! Walkable to downtown. Great communication - very nice and accommodating! We had a great trip :-)

Clean & Safe Apt w/Parking-Close to Downtown
Spotlessly clean. Although we didn’t use the kitchen, it was well supplied and very useable.

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

The Misty Mountain Hideout
My dog and I had a great time here and would recommend to anyone looking to stay in the area. We found lots of dog-friendly hikes and nature reserves nearby within 15-30 minutes . Otherwise we enjoyed the peaceful yard and small brook on the property. Beautiful and thoughtful rental, with very friendly hosts.

Elegantly Done Apartment in a Sun-Drenched Corner Lot House
Great location just a short drive into downtown. Also, we really enjoyed the local restaurants, ice cream stand, and coffee shop all within a few blocks of the place. The beds and coach are very comfortable, we would consider staying again upon our return. As other comments have mentioned, there is resident family above which I believe includes a younger child who can be heard running around a lot. This is an older building so I am guessing hardwood floors are throughout and that accentuated the noise.

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!

Quiet West End Retreat - parking - 100% Non Smoker
Sharon & Eric were very friendly upon arrival and throughout the stay. Eric helped us with our luggage and they both gave us great suggestions and had great conversation. The apartment itself is perfect for two people and in a nice neighborhood. Would highly recommend if you are looking to explore Portland!

Beekeeper's Cottage- Peaceful,Quiet - Ocean Front
Our stay at The Bee Keepers Cottage was amazing. The property met our needs perfectly and it was super cute and cozy. The host was very responsive and communicative. And for any star gazers out there, the sky on a clear night is mesmerizing.
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 by the beach!
Awesome place. Would book in a heartbeat again! Alyssa rocks too! Loved everything about this stay.

Top Of The Line Stay!
Great location, very clean and quiet. As described and would book again!

Comfy condo with loft by the beach!
This was a beautifully decorated space. The location near the beach was perfect! Cute little spot.

Rustic Willard Beach condo ten mins from Old Port!
You cannot beat the location with this rental. We love coming to Willard Beach with our pup, and when our old go-to BNB stopped renting we were so worried we wouldn’t find another. But this condo worked out so perfectly in terms of location (across the road from both Scratch Bakery and Willard Scoops, comfortable walk to the beach with several entrance options) and the actual comfort of the condo itself. The proximity to the beach was really a plus for us, as we didn’t have to get up as early to make the dog friendly beach hours! Host is responsive, and any household items (eg. soap, coffee filters) that were missing from the condo we could easily run down to get from Hannaford. The downsides: It is on a second floor walk up, which may be challenging for those with mobility issues. Hand railing is odd too. Bit pricey, couldn’t swing a full week this time around as the price shot up dramatically when I added Friday to the duration. But overall, really lovely!

Oceanfront condo, spectacular views
We’ve stayed here 3x so far and will always come back. This place is such a unique stay with live music right below. You can open the balcony doors and see and hear the ocean. The home is always clean and feels very homey. We truly love it here and will always choose to stay at this airbnb.

Modern Condo, Victorian Charm. Walk To Everything!
Super cute apartment in a great location and very responsive host! The apartment was clean and well stocked, and the Steve was very kind and responsive. He was also able to accommodate a very early check-in for us which was greatly appreciated. The location was great for getting around Portland. Our only complaint was that the free parking was not as easy/available as we had hoped, but the host did a great job compiling a list of other (paid) parking options. Overall loved it and highly recommend, just consider that you may have to pay for parking.
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- Ogunquit Beach
- Sebago Lake
- Wells Beach
- Scarborough Beach
- York Harbor Beach
- Story Land
- Popham Beach State Park
- Long Beach
- Surfside Beach
- Long Sands Beach
- Attitash Mountain Resort
- Pemaquid Beach
- Diana's Baths
- Fox Ridge Golf Club
- Coastal Maine Botanical Gardens
- Cliff House Beach
- East End Beach
- Brunswick Golf Club
- Palace Playland
- Pemaquid Point Lighthouse
- Ferry Beach
- Funtown Splashtown USA
- Cranmore Mountain Resort
- Purity Spring Resort
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