Holiday rentals with outdoor seating in Waldoboro

The Sail Loft is a peaceful, beautifully appointed space to rejuvenate and rest. The space itself is clean and thoughtfully designed with everything you need for a comfortable stay. The quiet morning with coffee and the calming atmosphere that made it easy to unwind. Highly recommend for anyone looking to slow down and soak up the beauty of the Maine. I’d absolutely stay again!

We absolutely loved our stay, the house is very private and comfy. The master bathroom and kitchen were both really nice. Beds are very comfy as well. I would definitely recommend this place to anyone

Thoroughly enjoyed our stay! We unexpectedly had beautiful cloudless days most of the week. Great location & easy to get to the Harbor and Southport both of which we enjoyed! Recommend the Carriage House for a really top quality meal as well as Blue Moon Cafe (good lobster roll) which was one of Shirin’s recommendations. Would totally stay here again!!

We had two nights to spend in Maine after a week long trip to Quebec. The lake house was a wonderful place to unwind after our busy trip to Canada. We spent our full day parked in the yard, enjoying the boats provided, reading, playing bags, and just sunning. It was a gorgeous day, and we loved it. The house is spacious, very well-stocked, and has many little amenities to make it feel like home. Highly recommend!

We loved our stay (late May, 2025). The weather did not cooperate but the house was perfect. Thank you Debbi!

What a beautiful and peaceful cottage to serve as our home base while on a family trip. We felt right at home, had everything we needed and plenty of room to spread out. Comfortable beds, awesome to have a washer and dryer, the parking spot could not have been more perfect! The deck was the most incredible part as we watched all forms of weather from the gorgeous spot. When we’re back in Maine next, we will return!

The accommodations were wonderful! Very well decorated, comfy beds and an amazing shower! There is a full kitchen with everything you would need! Ty is an amazing and super nice host! He provided fantastic recommendations for places to eat and things to do while visiting the area. Highly recommend!

Ammi was a wonderful host throughout our stay at her cottage. She was very responsive before and during the stay, answering any questions we had and providing great recommendations. The place was exactly as described and very clean. We would absolutely rent again.

You know it’s a lovely space when we come multiple years to stay! Amy is the nicest- a fantastic host with great recommendations for the area. The apartment is clean and spacious and full of rustic charm. Our kids adored the ducks they have on the property and the yard is wonderfully inviting! Can’t wait to come back next year 😃

This apartment was so clean, well decorated, well stocked and very comfortable. The location is perfect. So close to downtown Wiscasset, Boothbay and Freeport. This was our 2nd stay and we will return. Kathleen is a great host!

Absolutely amazing stay! The place was spotless, in a perfect location, and communication was excellent throughout. Katie is a fantastic host and I would love to stay here again!

Boo and Jonathan’s place is the definition of “the perfect air bnb”. This place truly felt like home - it was well designed, inviting, and charming. The small details (such as the delicious homemade pumpkin bread), the cozy blankets, fresh flowers and binder of local recommendations were all noticed and appreciated. We had the most wonderful stay - thank you!

We came here off season and it was beautiful. The place was clean, spacious, and warm- even on a brisk Maine evening. Downtown Damariscotta is lovely at this time of year- they were getting the town ready for Christmas. Great restaurants as well. Would definitely return.

If you’re looking for a peaceful, safe, clean, well-stocked and adorable place to stay in mid-Maine, I 100% recommend! It’s a quick drive to Camden which is chock full of restaurants, shops and a view of the water. It’s also a perfect central place to drive up or down the coast on your adventures. Cat was a great host and was able to answer any questions I had.

The place is very nice and private. Quiet neighborhood, yet close to the downtown area in Camden. Walking distance to the trail to Mt Battie. The apartment was very clean and comfortable. Jason was very friendly and had clear instructions on how to use everything. We really enjoyed our stay.

My partner and I have been staying at Penelope's place now for 4 years and we're always so happy to be there. The views truly are breathtaking, and the apartment is so cozy! Penelope is an absolute treasure of a human being as well. This is a hidden gem in Rockport and you owe it to yourself to stay there!

Great stay

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

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!

We had a great stay at Tysons place. Its a perfect location, only like 5-10 minutes drive from Old Port. The home is clean and beautiful. Street parking was super easy. Always space right on the side of the home. Each room has its own A/C. Would definitely recommend staying at Tysons place!

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.

Great place! Close to the beach. Easy and fast communication when we needed to specify parking questions.

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!

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.