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

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

Windham Wind Down-Lakefront, Dock, Kayaks, & SUPs
Our group was two small families with kids ages 6 and 8. Everyone had a great time. If you’re looking for a home to get out into nature, this is it. The private dock and lake gave us hours of time to play outside. Kayaks, paddle boards, and fishing off the dock was fun and all part of the house. Kids had a blast and so did the adults. Perfect for family summer vacation. We had a few rainy days but either played board games inside or went into Portland which is only 20-30 minutes away. Visited Mackworth Island in Casco Bay. Must do if you want to have a day excursion. The house well kept and easy to navigate. We spent more time outside on the lake than inside.

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
We loved our time staying here, the house was beautiful and just as described/ seen in the pictures. Randy was a great host and always very responsive with some great local recommendations. Would definitely love to return!

Breathtaking Bay Views!
I can’t say enough about what a nicely appointed home in a beautiful setting this is. I came for peace and tranquility and it did not disappoint. I haven’t had such good sleep in over 2 years. Highly recommend and plan to return next year! Thank you all so much for sharing your lovely home.

The Hendrick House
It has been a wonderful experience getting to meet and work with this couple! Very understanding and accommodating and beautiful home and location I highly recommend!
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

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
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!

Quiet West End Retreat - parking - 100% Non Smoker
A perfect stay. The accommodation is superbly located and you can easily explore Portland on foot. There are many restaurants, etc. nearby, the selection is great. Sharon and Eric were perfect hosts and we felt completely comfortable. The accommodation is very clean and has everything you need. The private parking space is also a big plus. Thank you Sharon & Eric for a great stay and for making us feel at home. We will be 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!
Condo rentals with outdoor seating

Oceanfront Condo with Awesome Views
Great stay

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.

KimBills’ on the Saco
We are a family of four and we stayed for four nights. It was larger than we expected and we were all quite comfortable. We loved that we could ski, swim, and have dinner without getting into our car on an extremely frigid (-17 degree windchill) day! It was a fun atmosphere and we loved our stay!

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 Windham
Total rentals
90 properties
Nightly prices starting at
$99 NZD before taxes and fees
Total number of reviews
5.1K reviews
Family-friendly rentals
70 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Destinations to explore
- Rentals with beach access Windham
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- Family-friendly rentals Windham
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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
- 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