Pet-friendly holiday rentals in Waldoboro

This was our first experience with an Air B&B and happy that it was with Spencer. Our main reason for the East Coast trip was to see our grandsons football games at Bowdoin College and it was a perfect location. We stayed for seven weeks and loved the experience.

I was looking for a small, waterfront place to stay with my dog to decompress and unplug. OakLeaf exceeded my expectations and was perfect. Sunrises and sunsets overlooking the river and sitting by a fire were spectacular and I stayed an extra night. Bill, his wife, and their dog Shadow were gracious hosts and knowledgeable about the area. I will be returning!

We had a great time! The fenced in yard was perfect for the dog, and a great location just 15 minutes to the downtown area!

Stayed with my wife and 2 year old son for a full week. Wonderful location walking distance to many shops, bakeries, restaurants etc. Blackout curtains in the bedroom were helpful for our son with naps and early sunrise. Playground a 30 second walk down the street which we used often. Private parking space directly behind the home was also convenient. We thought it was great value for the location and a nice alternative to booking an apartment or larger home when we spent the majority of our trip out exploring. Overall, we were very pleased with our experience.

Second stay at the farm house. Two weeks this time. We just love it here. Plenty of space yet cozy, everything you need, lovely outdoors space. We enjooed watching the chickens, dicks and horse next door. I wish we could stay for months. Thank you, Amy and family!

We absolutely loved our stay! We rented the house for 7 adults and 1 dog to celebrate a 31st bday! We loved being able to walk right down to the tasting room for a beer, cook a big dinner in the kitchen, play games, and watch the amazing vcr collection. Everything was clean and comfortable. So glad it’s a dog friendly space!

Great location, easy walk into town. Lovely place. on arrival had an issue with heat but Melanie responded quickly and we were able to rectify the problem quickly. Would definitely stay again. The dog enjoyed also!

Just as described! Very clean. Far enough to feel private but still close to grocery stores, shops, and nearby towns! Lisa is great at communicating and it was a seamless process! Had a wonderful new year’s getaway!

Friendly and responsive host. Place was beautiful.

I stayed there for two weeks and I would stay again. It was very quiet which is my number one need. Two it was clean. Three nice kitchen with all the appliances you need. Four Jeanmarie answered all questions quickly and clearly. Five lots of room in the house. Six it was nice and warm in the winter weather.

What a cute cottage with absolutely everything one would need Killer view

My return visit to the Boathouse was even lovelier than I hoped it would be. The location can't be matched by anything else I've seen. I enjoyed a September visit with my dog and was lucky to have pristine weather. I lived a very simple and healthy outdoors life and came home the better for it. The Boathouse is true to its description: it is simple and rustic and uncomplicated but well-equipped, and is perfect for one-and-dog, or for two people. A little coming-and-going from the neighboring houses meant that I didn't feel isolated. Margaret is truly an exceptional and friendly host who communicates promptly and clearly. I almost hesitate to share "my" Boathouse location with too many of my back-home friends because it feels so intimate and special. I already want to be back there. I offer my deep thanks to Margaret and to the place that I could - briefly - call home.

The perfect place for a weekend away with friends! Easy to find/get to, and less than 15 minutes from downtown Portland! The house was extremely clean, well stocked with anything you might need, comfortably furnished, and looked just like the listing. Susan was extremely responsive and helpful! Highly recommend, and we can’t wait for our next stay here!

My stay was very comfortable. The property was well kept and updated. The beds and furniture were were in perfect condition. Both the house and the grounds were exceptionally clean and well maintained. I would visit again!

BEAUTIFUL Home!! Tons of space to relax and spread out with our family! The beds were very comfortable! We really appreciated all of the bathrooms for our group! The kitchen was huge and so handy for preparing meals! I absolutely loved the style and atmosphere of this wonderful home! We also loved being able to bring our dogs!! We had a lovely time and we would most definitely come back!!! 🥰

My wife and I spent 2 nights here while traveling Maine. It was very relaxing and exactly what we needed towards the end of our trip. It was unlike anything I’ve ever experienced but I would absolutely do it again! We also fell in love with this restaurant down the road called “Farmhouse Beer Garden”.

Our family and I had a wonderful stay at Jackies, we are all originally from maine, and her home gives you everything great about maine. We really felt at home, it snowed christmas eve which made it even more beautiful ( The driveway was plowed out early as well). I brought a small christmas tree with us on our trip up, and when we walked in, the place was decorated for christmas, which was just amazing and so thoughtful. We definitly plan on staying again, the next time we are back in maine. Thank you again Jackie!

We thoroughly enjoyed our stay at Samantha's place in Cushing. To say that she is "very responsive" would be an understatement. She typically responded within 10 minutes no matter what my question was. She lives a short distance away which really helped facilitate things. We had a minor issue with the Internet which required communication with the service provider, but she coordinated everything and resolved it right away. The house is totally charming - old, a bit creaky and adorable - and well maintained (no issues there). We imagined how great it would be to visit in wintertime and snuggle up to a roaring fire. They have an expansive yard with gardens great for a short evening stroll. Forest habitat behind the property was great for bird watching. The area is absolutely beautiful - quintissential coastal Maine. The Olson House (local attraction) is a few minutes drive from the house. The grounds have a walking trail along the water with fantastic views of the coast.

Keith's place was such a cozy stay! The facility was spacious and well-ventilated. Keith was helpful, and the kitchen was equipped with items to cook with. Would love to stay again! The neighborhood cats are very friendly, I enjoyed interacting with them and giving them treats!

Margaret’s place is very homey with all the necessities for a family gathering. The neighborhood is beautiful and close to beautiful trails

Staying at Paul and Shankari’s retreat home was lovely. There was plenty of space for all of us (about 14 people) and the hosts left us great instructions and amenities.

It was great and work out well for us.

She made cookies the moment we checked in and delivered them to us with warm milk. Wonderful host with great knowledge of the beautiful Pemaquid region

Great location and place for short stay. The house is equipped with all necessary tools for comfort staying.