
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

Sunny 2-BR 5 min to Bates & River Trails
This is the 2nd time I've stayed at Emma's place. I came both times for a workshop and ceremony that took place in both Freeport and in Portland. Drives to Portland were the longest, and not too taking, and I chose to stay at Emma's place BECAUSE of the way the house holds me: the spaciousness, the attention to art and wisdom, the lighting and unfussy-yet-design-inspired furniture choices, the plant life, the textures and colors: all these things are soothing and welcoming. It was a pleasure to drive "home" exhausted, knowing what it feels like to open that back door.

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!

Grandma's 2 Bedroom Bungalow with loft
Rhonda’s house was so charming with its many decorations from the 1940s, 1950s. It felt very cozy and completely comfortable there for the five of us. The grands loved the loft with the toys, and we adults appreciated the awesome shower and towel filled bathroom. So nice! Very comfortable beds, well equipped kitchen, easy to get into entrance, porch a nice place to relax. Great AC, too. Beautifully clean and tidy. Very close to downtown Portland for all of the going’s on and super restaurants. We would definitely stay again.
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!

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
Ein perfekter Aufenthalt. Die Unterkunft ist super gelegen und man kann Portland problemlos zu Fuss erkunden. Es hat viele Restaurants etc. in der Nähe, die Auswahl ist gross. Sharon und Eric waren perfekte Hosts und wir haben uns rundum wohlgefühlt. Die Unterkunft ist sehr sauber und hat alles was man braucht. Auch der private Parkplatz ist ein grosses Plus. Vielen Dank Sharon&Eric für einen super Aufenthalt und das wir uns wie zu Hause gefühlt haben. Wir werden wieder kommen!
Condo rentals with outdoor seating

Oceanfront Condo with Awesome Views
Je recommande à 100%

Modern Industrial Beach Cottage
Très beau séjour! L’emplacement est parfait, tout ce dont on a besoin est sur place. Je recommande!

Light-filled Modern Central Penthouse w/Views
The apartment was just as lovely as it appeared in the photos online, and the sunlight was fantastic. The location was also great, with many terrific restaurants and bars within easy walking distance. I would definitely want to stay at Taryn's place again the next time I'm visiting Portland!

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!
We enjoyed our stay at Tyson’s. Lot’s of extra touches like fresh flowers, bottled waters, and ground coffee ready to go. Tyson had mini shampoos and conditioners in the bathroom too. The house was spotless. Our family was very comfortable for 3 days. The location being next to the freeway is noisy more so outside than inside but the AC unit fans covered it up well at night. And…..It did not take away from how much we enjoyed our stay whatsoever. Great noodle house and coffee shop within walking distance.

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.
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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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