
Cottage vacation rentals in Bailey Island
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Top-rated cottage rentals in Bailey Island
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Vacation rentals for every style
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Popular amenities for Bailey Island cottage rentals
Cottage rentals with a hot tub

Lakefront home, gorgeous views, hot tub for 2025
A great house and location right on the water. We arrived well after dark, Tom came and met us at the property to make sure we got situated. Plenty of room for a family of four and more. We enjoyed the boats and fishing and hiking in the area. The game room was nice to have on a rainy day. The kitchen has everything you need. Really enjoyed our long weekend here.

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

Sunshine on the River
We had a wonderful time at this vacation house in Maine. The views were breathtaking and the cottage was cozy. We thoroughly enjoyed our stay.

Old Orchard Beach Cottage
This was perfect for me, my daughters and granddaughter!! It was close to so many things and to Old Orchard Beach and the Pier. We had a great time there and would stay there again in a heartbeat!! Thank you!

Waterfront Getaway w/ Private Sandy Beach
This bnb was super nice and clean. Exactly like the description. Hot tub was a plus. I’d love to stay again in the summer to enjoy the lake.

Cottage with Whirlpool tub - Ross
Peter's place was the perfect spot for my girlfriend and I staying in Norway. The place was everything we expected and more! Clean, warm and cozy. We would definitely stay there again!

A peaceful place on the river
Janet is a national treasure. When I mentioned we were up here for our anniversary, she offered to have breakfast ready for us- the three of us sat in her beautiful sun room overlooking the river and talked about her amazing life’s work, her progress on writing her eighth book (she’s a genius) and had a lovely morning getting to know each other. The bedroom is beautiful and quite large, with a fireplace and sliding door for morning views of the river. I sat outside with coffee and watched the many different birds visiting the feeders, it was perfect and peaceful. We’re so glad we found this gem of a host and hope to come back next time we’re in town.
Pet-friendly cottage rentals

Bright, clean, private cottage near Higgins Beach!
We loved our stay at the Gull Cottage!! Karen and Steve were great hosts, incredibly friendly, helpful, and responsive. The cottage was well stocked with everything we needed to enjoy our stay. The guide book and guest book were great touches as well, and we would happily stay again next time we come up to Maine! We could not recommend the Gull Cottage more if you’re looking for a great and cozy place to stay near Portland!

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.

Tall Pines Hideaway
This place is perfect! The house is so cute and cozy we didn’t want to leave. The hosts left a hand written card and a bottle of wine for us when we arrived, which was so thoughtful. Beautiful views and tons of privacy. Would highly recommend this stay to anyone!

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!

Sunset Haven - Little Sebago Lake
Absolutely loved our stay at this lake cabin! It's nestled right on the water, making it a perfect spot for peaceful mornings and unbeatable fishing. The sunsets over the lake are absolutely stunning — a real highlight of the trip. The cabin itself has a rustic charm, filled with unique vintage touches that make it feel cozy and full of character. It's quiet, far enough from the city to truly relax, but still conveniently close to town if you need anything. A wonderful place to unwind and make lasting memories with family. Can't wait to come back!

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.

Rustic Pebble Cottage in beautiful Bridgton, Maine
Pebble Cottage was so peaceful yet close to everything. We kept ourselves quite busy locally and Cheryl's place was a perfect spot to unwind and relax at the end of a busy day. The host is a beautiful artist and an exceptional, sweet human being. We hope to return in the Fall. Thanks Cheryl!
Private cottage rentals

Cozy cottage with great yard
If you love being near a peaceful and beautiful ocean setting and a cozy cottage vibe this is the place for you. Renee is nearby and very responsive if you need anything. Otherwise, you can just enjoy the setting and easily take yourself to the nearby restaurants or cook for yourself. A short walk to my favorite beach on earth. Check out the sandbar at low tide.

Cheerful 1 Bedroom Cottage Steps From The Ocean
Wonderful place clean and very cozy house I indicate

Waterfront Cottage - early Summer Availability
We really enjoyed our stay at thie coastal cottage! It was a great space for our family of 4. It is secluded, private and "tucked in" which we enjoyed- a nice departure from a city atmosphere. The unit came with many amenities and was super clean. It's important to note the cottage is about 25 minutes from restaurants in Rockland and 35-40 minutes from Camden, but we really enjoyed the longer car rides and allowed a chance for our little ones to nap on the go!

Custom Built Quaint Knotty Pine Cottage
We felt truly comfortable and at home in the Knotty Pine Cottage. We spent 19 days there! My husband was working again in the area and the job site was 5 minutes away. On his days off we took advantage of hiking the numerous Boothbay Region Land Trust properties. We highly recommend Porter Preserve, Oven's Mouth Preserve and Oak Point Farm. We loved walking around beautiful Ocean Point and an afternoon on Popham Beach. We also spent an afternoon reading our books at Barrett's Park. The house is well stocked with everything you'll need to prepare meals and there is a Hannaford Grocery store 10 minutes away. We recommend The Thistle Inn in Boothbay Harbor if you enjoy crabcakes that are made from scratch. We're looking forward to our next trip back to Southport and hope the cottage will be available. Many many thanks to our responsive hosts! They made us feel welcome and comfortable in their home!!

Cozy 2 Bedroom Cottage 50 feet from the Lake
Don’t tell anyone about Shelley’s place! We want to be the only ones to be there!!!!! We had a beautiful time ! Me, my daughter and her 2 yr old son. The lake is soooooo clear and relaxing. Canoed every day. Loons in the lake everyday. Went and picked blueberries and went to the children’s museum😃 Close to Portland! We’ll bring the Daddy next time! Thanks Shelley

Private oceanfront cottage, great views, and float
Such a beautiful spot--Christine's house has gorgeous views, a dock and many kayaks. We enjoyed our stay--sitting on the deck, seeing the Northern Lights (!!)--thank you Christine for the heads up! Harpswell is a special place and this beach cottage is special as well. Loved the view from the spacious bedroom. Great hiking and local seafood.

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
- East End Beach
- Surfside Beach
- Fox Ridge Golf Club
- Brunswick Golf Club
- Popham Beach State Park
- Parsons Beach
- Portland Museum of Art
- Mothers Beach
- Ferry Beach
- Pemaquid Beach
- Coastal Maine Botanical Gardens
- Cliff House Beach
- Dunegrass Golf Club
- Palace Playland
- Funtown Splashtown USA
- Laudholm Beach
- West Shore Sandy Beach
- Arundel Beach
- Crescent Beach State Park
- Wolfe's Neck Woods State Park
- Pemaquid Point Lighthouse
- Western Beach