
Cottage holiday rentals in Bailey Island
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Top-rated cottage rentals in Bailey Island
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Popular amenities for cottage rentals in Bailey Island
Cottage rentals with a hot tub

Cozy Cottage close to Beach, Pool and more!
Dear Tim and Kimberly - I wanted to express how much we enjoyed our stay at your delightful two-bedroom cottage. The accommodations were not only beautifully furnished but also incredibly comfortable. The added amenities, including the pool, hot tub, and gym, made our stay even more enjoyable, offering plenty of options for relaxation and fitness. We also loved how close the cottage was to the local restaurants and the beach—it was the perfect location for a relaxing getaway. Your attention to detail made all the difference, and we couldn't have asked for a better experience. I will definitely recommend your place to others and look forward to returning in the future! Janelle Q PS - I live in Florida and upon my return from Maine, am being greeted by Helene. JQ

Make this family-friendly cottage your summer spot
Jessica was very communicative and her place was in a great location to access the area’s attractions. A comfortable home away from home. We enjoyed the pool and wish we had stayed longer. Thank you!

Maine Lakehouse, 3 Bedrooms, 2 baths, waterfront
Nice private area, close by to a few small-towns for groceries, gas, etc. Property was very scenic and often only sounds that could be heard were birds. Slept 5 comfortably and never felt crowded. 10/10

Cozy beach cottage with pool & hot tub
Lovely one night stay at this sweet little cottage! Grounds are well-kept, enjoyed morning coffee on the front porch. AC kept it nice and cool. Convenient location close to a great donut shop- Congdon’s and our favorite ice scream spot- Scoop Deck. Chloe is a gracious host and even granted us a late check-out!

Lakeside Cozy Cottage in Nature | Hot Tub
This trip was more than we could've ever wanted! The property was lovely and the hosts were more than accommodating and made sure everything was as comfortable as it could've been! I'd recommend anyone to book with these hosts and I will definitely be booking again!

Fully Renovated/4min to K-port/HotTub/Game Room
We had a great stay at Audrey & Seb's place. It was spacious, beautifully decorated, and extremely clean. The beds were super comfortable, the location was private and close to town, and there was so much thought put into all the little details. What an absolutely wonderful place. Thank you so much!

Beautifully renovated 2-bedroom cottage
Everything was so perfect !! thank you for hosting us !!

Megunticook Retreat
The perfect place to stay for a peaceful vacation - the home is extremely well appointed and had everything we could possibly need and more. The lake is even more beautiful than the photos and we enjoyed the kayaks and hot tub each day we were there. We would highly recommend.
Pet-friendly cottage rentals

Timeless Tides Cottage
The cottage was beautiful and comfortable, and the setting was gorgeous. We were very comfortable there and would definitely go back! Carlos and Karen left very helpful and thoughtful local recommendations for food and activities. This place is a gem!

Relax at this Pet Friendly, Lakefront Getaway
This was a great get away. Right on the lake with the convenience of using their kayaks, row boat, and peddleboat. Also had an array of life jackets for everyone to be safe. Scenery is beautiful, location is peaceful! We read, kayaked, played pinpong in their basement, sat around the firepit and listened to nature! The house is exactly how you see it in the pics, plus better! The home is spotless and has everything you need! Host Heidi is very responsive! They even have many board games and puzzles to play. I would highly recommend this property and plan to rent again. Thank you Heidi for sharing your home and for a lovely weekend. Jamie Hale

Cottage on Todd Bay
Our group of 4 had a wonderful stay here. It had everything we needed and John was extremely helpful. We cooked several meals and visited nearby attractions.

Osprey Cottage, peaceful setting, walk to beach
Elizabeth was a wonderful host and her home is perfect for a peaceful, relaxing vacation. The house was spotless, well appointed, and very cozy. The short walk to the beach and town market is really convenient. Her rental is a perfect home base if you’re visiting Portland or exploring the Maine coast nearby.

Camp Wigwam
Great person, she really went over and above what she would have been expected. The dock with boats were great, my boys love the lake. The place was clean and very well decorated. Lots of extra appliances. Washer and dryer is very nice when you are on a lake. Nothing to complain about. If you stay here and especially if you have kids you will be very happy.

Pet Friendly Audubon Bring Your Fishing Gear!
What an amazing setting! Right on the water. We saw seals, osprey, and, we think, an eagle.Also the most beautiful sunrise. The house is cozy and comfortable and really really clean. We found everything we needed and some thoughtful extras. Tamara is an excellent host!

Our charming,oceanfront, Bradford point cottage
Just amazing!! This is the second time we have stayed at this air bnb! The cabin is quaint. You cannot beat the views!! It is just absolutely perfect!

Waterscape Cottage - private waterfront
We had a wonderful time at Ann’s. The cabin was great and exactly as described, clean and very comfortable. The property is amazing with lots of privacy and in a great location to explore the Maine coast during the day. Don’t miss hiking down to the trestle bridge to see the herons. Ann thought of everything to make sure we would be comfortable during our stay and she was happy to offer suggestions on places to go and things to see.
Private cottage rentals

Tranquil waterfront cottage
This Lakeside Retreat was a perfect weekend escape for two couples. In late September, we seemed to have the pond to ourselves and enjoyed sharing time around the firepit overlooking the lake. The Bathroom was spacious and one level up from the bedrooms downstairs. The kitchen had everything needed to prepare an excellent meal. I would highly recommend this cabin to a a small group of friends or family looking for a great location near Portland and Lake area attractions.Our host Bobbi was very responsive.

Cobb Cottage: Lake Beachfront Fri-Fri Jul-Aug
My husband and I spent 6 days here for our anniversary. I wanted a location on the water and close to visit all the major coastal towns in Maine. This was perfect! The home, felt like home, and everything was clean and beautiful. Adam was very helpful whenever I had any questions. Sipping coffee every morning on the back porch and watching the sunrise over the lake was so peaceful. Grocery store close by and great hiking/walking areas right out the front door. Can’t wait to come back and bring the family.

Big Sebago Lake Rentals Waterfront w Private Beach
Beautiful location, perfect stay with amazing hosts! This was the perfect getaway for our family and we cannot wait to go back! The location can't be beat and Kate and Barry went above and beyond to make sure we had everything we needed. Highly recommend!

Alvan Riccar Cottage 3 at Poland Spring Resort
Loved it! It was relaxing and deff worth the price. We’ll deff be back next time we’re in the area.

Seaside Escape
The location was amazing. Just a few steps to Crescent Beach. I actually took my coffee down there and watched the sunrise in the morning. So beautiful. The cottage was clean and comfortable. Kristin was very responsive and helpful. Don't miss out on the clam chowder at the Lobster Pound less than 100 meters away. We'd definitely come again.

Hidden Haven A Rustic Retreat In St. George, Maine
Beautiful cabin in quiet and peaceful surroundings. Closes to attractions and multiple small towns with things to see and discover. Michelle and Dan were great hosts, everything we needed was in the cabin! They had a book of area things to do. They answered right away when we texted. I would definitely recommend their place!

Oak Grove Cottage at Sennebec Pond
I have zero complaints about Gordon's home. Everything was accurately described and the property was beautiful! it is right on the pond and the pictures do it justice. Yes, it's a little small and gets cold in the winter but it's worth it if you want to stay somewhere pretty without breaking the bank. Also, he has 3 heaters. We didn't leave them on because we were gone a lot of the time but it probably would have stayed warm if we did. This is really a great property for a couple! Highly recommended.

Saco Cozy Cottage! Minutes From Old Orchard Beach
The cottage was perfect for our needs and had everything! Auria was extremely helpful and responded to us quickly! I would definitely stay there again!
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- Wells Beach
- Ogunquit Playhouse
- Surfside Beach
- Fox Ridge Golf Club
- Brunswick Golf Club
- Popham Beach State Park
- East End Beach
- Pemaquid Beach
- Parsons Beach
- Mothers Beach
- Middle Beach
- Palace Playland
- Portland Museum of Art
- Cliff House Beach
- Dunegrass Golf Club
- Ferry Beach
- Wolfe's Neck Woods State Park
- Pemaquid Point Lighthouse
- Coastal Maine Botanical Gardens
- Arundel Beach
- Laudholm Beach
- Funtown Splashtown USA
- Crescent Beach State Park
- West Shore Sandy Beach