
Vacation rentals with outdoor seating in Cumberland County
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Top-rated outdoor seating rentals in Cumberland County
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House rentals with outdoor seating

Wine Down Retreat: Spacious Home Near Downtown
It was a great place for a large group and the hot tub was key! The driveway to get up to the house was long and there is a steep hill at the end so you should be prepared with AWD if you're going in the snow. Also the largest primary bedroom with the wood stove has a door that connects to another room and that would have been good to know since we were traveling with couples. The primary bedroom does have its own staircase to use the first floor bathroom, but the shower is in the adjoining room so it could be a bit awkward if it's two separate families. Overall, it was a great place to stay in Bridgton - one of our favorite towns with lots of cute restaurants (Beth's!) and fun things to do.

Charming Coastal Home
We were remodeling our home and needed a place to stay for over a month and this place did not disappoint. The home is welcoming and super clean and neat. There were plenty of amenities for cooking and it was well stocked with paper products and a few toiletries as well as plenty of linens. It is so close to many great businesses and walkable to an excellent Gluten free bakery. The host was extremely kind and responsive to our needs- my son (7) said this home felt just like our own home. His favorite part was the “fancy fridge” that we could play music on and see different pictures according to the weather haha. Definitely a great place.

By the Sea - sleeps 11! Walk to beach
The accommodation is located in a quiet area and a short distance from the beach. I highly recommend this affordable place for a stay in Old Orchard Beach!

Faith Lane with community pool
Beautiful house! Lots of space and had everything you need for your visit. The community pool was great too. Very close to Portland and easy to get to other areas of Maine from the location. Jason was a great host and very responsive and helpful! Only minor complaint was mattresses upstairs were a little on the firm side but other than that the house was great!

MAINE: Home away from Home
My husband and I lived in the place for 43 days. It was PERFECT! The house is better than in the photos. A lot of space. Laundry in the house. Kitchen with everything!! Super comfortable beds. Really good shower. Check in super clear. Michelle and her boyfriend were super nice to us. They helped with snow cleaning, they decorated the place for Christmas and it was so cute!! In new year`s eve we asked if we could bring some guests and they said yes. They are really good hosts and I definitely recommend this place! The location is really good - close to many restaurants and main roads. It was PERFECT for us!

Casa Azul - short walk to the beach
Jenelle’s house was perfect for our family stay in OOB. It is a short couple minute walk to all of the restaurants and shops on the main strip. Jenelle had available beach supplies including towels, a wagon, beach chairs and umbrella for us to use. Jenelle was very friendly and responsive. I would definitely recommend staying here!!

"Good Vibes" 4 Wonderful Seasons @ Portland Home!
We enjoyed our stay at Angela's. Communicative host, nice clean place, easy to find. Great for a weekend trip!

"Garden Off Eden - Adam & Eve"
Lovely place to stay for a beach vacation, and unusually well-equipped with everything you need for the beach - towels, wagon, toys, chairs, umbrella. Would for sure stay there again! The hosts are close by and super-responsive.
Apartment rentals with outdoor seating

Bright & Sunny Apartment with Patio
The place was clean and beautiful, the neighbourhood felt very safe and peaceful too. Victoria proactively shared all details and even left recommendations for places to go to and things to do! Overall, it was a peaceful and fun stay! Thank you Victoria :)

Sophisticated Charm at an unbeatable price!
Susan’s home was perfect for our long weekend in Portland. We could easily walk everywhere and lots of great shops, restaurants and bars very close. Her home was very comfortable and a nice large space for us to all enjoy!! Also her home was located in a great neighborhood!! We would definitely come back again!!

Sunny West End Apartment With Private Courtyard
Delightful place to stay in Portlands West end. It is easy walking distance to everywhere…. downtown and even the East side. Great restaurants in the neighborhood from breakfast to dinner. The apartment was immaculate and was stocked with just about everything you’d need. The shared yard was charming and felt very private. We have family in the area and I hope we can stay there again and again. It was much more comfortable than a B & B. Lorie was very responsive to anything you might need.

The Globe House: Amazing Sunsets Walk to Breweries
We loved the common areas and the walkability, and would come back. The living room and dining room are spacious and very nicely furnished, and the kitchen is equipped with everything you could need. The selection of kids toys and baby books is great. The beds are not a selling point, but on the whole we found the full package more than worth it. If you're traveling with kids, I'd recommend bringing an eyeglass repair kit just in case they accidentally lock the twist-lock bedroom doors behind them (as ours did).

Spacious 1st floor New England charm.
There's so much that can be said about this place and the area. We stayed for a week and barely scratched the surface of what's available to do. Within 15-20 minutes of driving, you'll find both sand and rocky waterfronts to explore, Island ferries, forest hiking, and countless amazing restaurants. Coming back to this place after each day of exploring felt like coming home to rest and recharge for the next day. Comfortable places to sit/sleep, conveniently supplied snacks, and great material to review what to put on your list for the next day. Please take my advice and stay here if you want to have a peaceful and fruitful stay in the Portland, ME area.

Bright and cozy Munjoy Hill neighborhood apartment
This gem of an apartment gave us so much peace and joy on our quick getaway to Portland. The interior reminds me of beautiful homes in Denmark and Norway - humble, functional, cozy, and lovingly designed. Both bedrooms and the washroom were spacious, comfortable, and clean. Loved watching the sunset over the amazing view in the living room, and the cute park/sunset spot just a quick walk away (perfect for bringing our puppy). Sadie was a gracious host and made us feel so at home. Would definitely visit again!

Parkside Retreat on Portland's Eastern Promenade
The apartment was clean and comfortable with a beautiful view of the promenade. The kitchen and bathroom looked recently updated compared to the rest of the apartment, and they were beautiful. It was relatively quiet for a multi-unit building, which made it the perfect place to relax after a long day of exploring the town only a short distance away. The only thing I would say that wasn’t my favorite part of the apartment is that the kitchen sink is very small and the faucet is extremely sensitive. I got wet many times, but thankfully there was a powerful dishwasher that took care of the dishes for us. Overall loved staying here and would book again if we returned to Portland. Highly recommend!!

The Yankee Dugout
Host was great and friendly. Beautiful neighborhood. Apt was very clean and comfortable. Many extras like Keurig, coffee, tea hot chocolate and water bottles. Cozy extra blankets, fans and fireplace. Bathroom was clean and had liquid soaps, shampoo etc. Not a full kitchen, but all you need. Would definitely stay again.
Condo rentals with outdoor seating

Oceanfront Condo with Awesome Views
This was my 3rd time staying at Kevin's AirBnB and it is always great! The bed is very comfortable and the entire place feels cozy. To top it off, there is the perfect view of the water from the balcony. It has everything you need for a little beach getaway. Will be staying again!

Modern Industrial Beach Cottage
It was a cozy stay and very nice to be so close to the beach! Thank you, Wendy!

Pet-friendly brewery lovers dream w/fenced yard
Really nice place, great location. The yard is a nice bonus. We had issues upon arrival and the hosts do take a bit to respond. But they were very helpful in resolving everything, so no complaints. Great stay overall. The bed and bedroom is very small but we made it work!

Cozy condo by the beach!
The perfect little getaway! While many restaurants and places in the general area were closed due to the season, it was still just what we needed! We had a cozy weekend in. Would definitely come back!

Comfy condo with loft by the beach!
Very cute place in a great location! It’s a little small, so the ladder is a bit in the way of getting to the kitchen. Think “tiny house” feel, in a fun way. Big people might struggle a bit, but otherwise everything is very functional and practical. Check in and check out is super easy.

Stylish Condo at Old Orchard Beach!
This was the cutest condo. Exactly what the pictures showed. Very clean and everything we needed. It’s so close to the beach, we enjoyed that on a beautiful fall afternoon! We also enjoyed how close it was to the pier area…..we had to get pier fries! We enjoyed our stay!

Rustic Willard Beach condo ten mins from Old Port!
We’ve stayed at Dave’s condo a couple of times now. Each time we have thoroughly enjoyed our stay. The place is in such a wonderful location in South Portland and Dave is very communicative and friendly with anything we may need. Definitely recommend a stay if you’re looking to check out the Portland area and enjoy some beach time while you’re at it!

Oceanfront condo, spectacular views
I booked wendy's place for the wife and I's honeymoon and it was perfect, was nice and cozy and the view of the ocean was amazing. Also being so close to so many attractions gave us plenty of things to do and memories to make.
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- Wells Beach
- Attitash Mountain Resort
- Cranmore Mountain Resort
- Story Land
- Ogunquit Playhouse
- Long Beach
- East End Beach
- Surfside Beach
- Mt. Abram
- Long Sands Beach
- King Pine Ski Area
- Purity Spring Resort
- Portland Country Club
- Powderhouse Hill Ski Area
- PowderHouse Hill
- Ledges Golf Club
- York Golf & Tennis Club
- Little Beach
- Crescent Beach
- Arundel Beach
- Parsons Beach
- Mothers Beach
- Laudholm Beach
- Middle Beach
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