Cottage vacation rentals in Bailey Island

The most beautiful place, exceeding all expectations. The views are spectacular. We breathed in peace and tranquility. A fabulous place to celebrate my 80th birthday with the whole family -- 16 of us. Everyone was comfortable in the space. In addition to being the perfect host, Samantha provided surprise extras which was such fun! Just a few of the highlights: S'mores at the firepit, lobster dinners, seals, bald eagles and fireworks. She made our stay truly memorable. My family gives the place the highest recommendation.

A great spot tucked away!! House was cute and as shown in the pictures, is right on the water and has some great views! It rained the majority of the time we were there so didn’t get to take advantage of all the outdoor amenities, but would have if better weather! Host was very friendly, communicative and responsive!

Was a great place for a weekend get together with our family. Right on the water and a great throwback feel but with all the amenities.

Great clean air bnb. Accurately as described.. looks good in photos but even better in-person. Bed was comfortable. Would rent their properties again.

We absolutely loved this spot. Great location, very clean, and spacious!! We will be back, thanks for an awesome weekend!

Perfect for what we needed for a weekend getaway. So peaceful and a lot of interesting wildlife. We saw so many different types of birds! The hot tub is spacious and easy to use.

Wonderful,private, well equipped cottage on pretty pond. Owners quick to respond to our texts. Relaxing hot tub and fantastic sauna! Many restaurants and breweries within a 30 minute drive. Book it ..... you won't wanna leave!

The place was quiet & cozy with everything we needed. Mini split AC in both living and bedroom. Two comfy queen beds. Small patio. Everything we needed and great location between Kennebunk and Ogunquit! Would recommend.

We had a fantastic time at this cute and cozy cottage! It’s within 15 minutes of basically anything in the Portland area and the cottage itself is so charming and inviting. We only wish we had planned to stay here longer!

Beatiful cabin on the water, thoughtfully decorated. I loved the layout, plenty of seating areas and lovely decor. There is only one small bathroom which may be an issue with more than 2 or 3 guests, but worked out perfectly for us. We saw deer twice when driving down the trail to the house which was exciting! Loved using the firepit outside. The only bummer was that the dock wasn’t in the water yet. I still managed to use the kayak but would not advise attempting without the dock lol. Wonderful host, David was very responsive and had a nice bottle of wine waiting for us on our arrival. Would 100% come back

Tammy describes her sweet cottage perfectly. Water views are spectacular with options to fish off the dock, sit in the backyard to warm up or sit on the bluff to cool off. It was perfect for this girl and her dog to re-set in solitude. Most places on the water have sensitive septic as described so you want to consider that if there are more than two guests. I enjoyed my endless walks on Popham beach (no dogs 4/1-10/1)) and was thrilled to be there in the off season. I barely saw anyone! Reid State Park was also spectacular and more opportunity to walk my dog on the trails. Tick season is a bit of an adjustment every year but not a problem if you prepare yourself and your furry friends. A perfect place for a great book, wandering around historic Bath, and easy meal prep. I stayed 2 weeks and appreciated all the thought Tammy put into anticipating what a traveler might need.

A Perfect Waterfront Escape – 5 Stars My wife and I had an unforgettable stay at RK North Waterfront Cottage. From the moment we arrived, we were welcomed by breathtaking views, fresh coastal air, and a sense of peaceful seclusion that made this trip truly special. The cottage itself was spotless, beautifully maintained, and tastefully decorated with cozy touches that made it feel like a true home away from home. We especially loved the spacious deck overlooking the water — perfect for morning coffee or evening wine while watching the sunset. The hosts were thoughtful and responsive, ensuring we had everything we needed without ever being intrusive. Whether it was relaxing by the fire pit, walking along the shore, or just enjoying the tranquility of the surroundings, every moment felt effortless and restorative. If you’re looking for a quiet getaway with charm, comfort, and stunning waterfront views, this is the place. We’re already planning our next visit. — Eric & Juliet DiNoto

We had a lovely stay at Jeff's place in Friendship and appreciated all the thoughtful touches there. It was wonderful taking the kayaks out to explore the surrounding islands. I would also recommend the lobster rolls nearby at the Jameson Point restaurant.

We really enjoyed Elizabeth's house. It was beautiful and peaceful. The dock and beach were great. Communication was awesome! would loved to stay stay again.

Barbara place is awesome for a couple plus I child nice quiet area very clean and it private. Barbara is a great host you will love this spot it feels like home we will be back

We had such a great time staying at Emily's awesome retreat. It was our first mini-vacation with our dog and we were looking for some peaceful, wide open space to let her roam free. We absolutely got that with this home and thoroughly enjoyed the town, as well. Emily was super responsive whenever we did have a question and provided us with a great list of places to check out around town. Would absolutely stay again. Thanks!

A very cozy, charming cottage right on the ocean! Beautiful! Would definitely recommend to all that want a secluded, private area to stay in!

Dan and Jane have a beautiful home. They were extremely kind and I can’t thank them enough for allowing me and the kids to meet their horses. It is a wonderful property on a serene landscape. The pictures don’t do it justice. We will certainly be back.

My wife and I stayed at Viktor's place for our honeymoon. As soon as we walked through the door it felt like we were in a second home. We loved using the projector and home theater setup to play Nintendo Switch and watch Netflix. I liked that the bedroom had its own separate A/C unit from the living room. Made it so much easier to set the temperature during the day and evening. The combined washer/dryer unit worked great and didn't have any issues drying our clothes. Nearly every morning we were greeted by neighboring deer who came to feed on the backyard grass. The surrounding area (Georgetown, Bath, and Boothbay Harbor) are really great to find good food, parks, and entertainment nearby. I highly recommend this place. It really is a gem in the middle of the forest.

This stay was absolutely what I needed. Housing is close together so I was slightly confused about which house at first. But, once I knew, it was very accessible and easy to get settled in. Shawn was very great at checking in and making sure we checked-in & out okay. The neighborhood is very quiet. The house is located right down the road from two different state parks as well as a few amazing restaurants. Overall, the house was extremely clean and the internet was very quick. I would definitely stay here again!

Amy’s place suited us perfectly — not far from my family in Portland, comfortable accommodation, furnished and decorated with flair, and best of all, a little beach down the street that we visited for our daily swim!

Our stay at Thistle Pond Cottage was incredible! Alexis and Hamish have really designed a space to make you feel right at home. The kitchen was seriously amazing, so many great touches and the bedrooms and bathrooms are INCREDIBLE. The shower was one of the best I’ve ever taken, hahah. Not to mention the nature of the surrounding property! The cherry on top was daily visits from Alexis and Hamish’s sweet Great Dane, Leah!! I brought my 14mo old son on vacation with us and it was the PERFECT place for him, he loved it. We felt right at home and would love to come back!! P.S. the homemade sourdough was some of the best I’ve ever had!! We loved Maine and our stay at the cottage. Highly recommend, especially for travel with babies!

We wanted the full "Maine" experience and that's exactly what we got! The view from the cabin into the harbor looked just like a painting. The cabin itself was so cute and perfect for our family of four. The location was great. We took a couple day trips up to Camden and down to Boothbay Harbor. We didn't want to leave!

Overall, it was a great experience! Very peaceful and on a private road. I appreciated a clean and welcoming place! I would recommend this spot and stay here again. Owner was very kind and responded to any questions I had. Only thing that could improve was the kitchen layout. Kitchen iteam were in odd locations. I had to open each cabinet to find the oven mitts. This is a very little critique, and I would still rate it five out of five stars!