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Cottage holiday rentals in Drakes Island

Find and book unique cottages on Airbnb

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Popular amenities for Drakes Island cottage rentals

Cottage rentals with a hot tub

Superhost
Cottage in Wells
4.94 out of 5 average rating, 47 reviews

Make this family-friendly cottage your summer spot

NicoleRating, 5 stars9 months ago
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!
Top Guest favourite
Cottage in Wells
4.97 out of 5 average rating, 62 reviews

Freshly Renovated, Family-Friendly Coastal Cottage

JorgeRating, 5 stars2 days ago
My family and I loved staying at the Seaholly cottage. The beds were extremely comfortable and the cottage was decorated beautifully. Lexi was very considerate when stocking the bathroom with every toiletry you could possibly need. The cottage is in the perfect location and very close to beaches, shops, and restaurants. Highly recommend staying at the Seaholly Cottage! You won't be disappointed! My family and I can't wait to book with Lexi again. We had a great vacation!
Superhost
Cottage in Wells
4.88 out of 5 average rating, 42 reviews

Beach Dreaming

ArtemRating, 5 stars7 months ago
A nice private cottage in a quiet community that was super handy for us to stay until we secured our house in New England. Everything is in place for comfortable living. We lived there for a month long and the hosts were always responsible.
Top Guest favourite
Cottage in Wells
5 out of 5 average rating, 49 reviews

Paradise Found Minutes from Ogunquit | Heated Pool

JenniferRating, 5 stars2 days ago
I truly can’t say enough positives about Stephanie’s place! First, the cottage looks even better in person. Second, the little details make all the difference from the quick response time, welcome card and lobster bag, a very informative welcome binder, and a fully stocked home which when added together, felt like OUR home! Some who is walker bound, found the property to have comfort height counters and toilet in the bathroom, two anti slip step stools to get into the bed if you’re short like myself, and remotes for everything (including instructions to use everything in the binder). If you think you need it, Stephanie supplied it from board games, lobster pot, cocktail kit, to a crockpot and a Bose speaker in the kitchen. There was a rainy day so afternoon vacay naps listening to music was a vacation-like you can get! Only suggestion would be there are closets in the bedroom but they have shelves. There are no places for hanged clothing. Bring some hangers, use hooks on bathroom door!
Guest favourite
Cottage in Wells
4.94 out of 5 average rating, 16 reviews

Beautifully renovated 2-bedroom cottage

LisaRating, 5 stars9 months ago
Everything was so perfect !! thank you for hosting us !!
Guest favourite
Cottage in Northwood
4.96 out of 5 average rating, 102 reviews

The Loon Nest, Waterfront Lake House, Wood Hot Tub

KristieRating, 5 stars1 week ago
Nice welcome basket with snacks and water bottles in each room with plenty of towels. It is very quiet and peaceful at the camp. It is great for relaxing and hanging out and there are places to eat just a few miles away. I would not stay here if I were looking for a place to swim, while it’s a beautiful water view, the shore is tiny and the vegetation in the water is too thick and slimy to swim. Beautiful sunsets over the water. If you are looking for a quiet, slightly rustic camp in the woods with waterfront views then you won’t be disappointed here.
Guest favourite
Cottage in Wells
4.75 out of 5 average rating, 20 reviews

Contemporary Cottage With Ocean View 13

AudreyRating, 5 stars1 month ago
Great place! Very cute home with very communicative hosts.
Guest favourite
Cottage in Wells
4.93 out of 5 average rating, 45 reviews

Cottage in Wells Maine

DavidRating, 5 stars6 days ago
Great cottage with a perfect location. Not too close to the ocean but close enough. Grocery stores and other shops within a mile radius. 10-20 miles gets you to many other small Maine locations.

Pet-friendly cottage rentals

Guest favourite
Cottage in Eliot
4.99 out of 5 average rating, 149 reviews

Salty Mermaid Cottage/Boat House

GaryRating, 5 stars2 weeks ago
My family and I loved Skye's place. It was very private with a great view of the river and a nice sunset. Lots of different sea birds including a family of geese that had just hatched. Skye's place was very well equipped with all the little conveniences we would normally supply ourselves from coffee and creamer to ice in the freezer. The location was perfect for us, because the focus of our trip was shopping. Less than ten minutes from the outlet stores We would definitely stay there again when in the area.
Top Guest favourite
Cottage in Middleton
4.99 out of 5 average rating, 104 reviews

Lovely cottage on Sunrise Lake, Middleton, NH.

StephenRating, 5 stars3 weeks ago
They were accommodating, flexible, and very gracious. They had an entire binder of information with details about where to find fans, towels, flashlights, how to work the shower, heat, grill, and about anything else you can think of. It also had emergency services, restaurants, places to have a good time, and good details about checkout expectations. Overall we were extremely happy with the property and our stay, and were honored by the personalization they did for us specifically as it was our Honeymoon and they wrote us a custom note by hand for when we arrived. Highly Recommended - Will Rent Again!
Top Guest favourite
Cottage in York
4.9 out of 5 average rating, 120 reviews

Cozy Cottage by the Sea

ShaunRating, 5 stars1 week ago
Another great stay at this place! It’s been consistently a great spot for us. Perfect for a walk to beach or into town. We love it and will definitely be back.
Guest favourite
Cottage in Gray
4.91 out of 5 average rating, 213 reviews

Sunset Haven - Little Sebago Lake

TiffanyRating, 5 stars2 weeks ago
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.
Guest favourite
Cottage in Bridgton
4.91 out of 5 average rating, 185 reviews

True Maine Artist Cottage with Outdoor Shower

KateRating, 5 stars1 week ago
Super cute cottage! I really enjoyed a few peaceful days there on my own, it was exactly what I was looking for. It's very charming and has everything you need. Like others have mentioned, you can definitely hear the road noise so it doesn't feel totally secluded but that didn't detract from my stay. Emily was a great host, provided lots of helpful information, and very quick to respond.
Superhost
Cottage in York
4.77 out of 5 average rating, 301 reviews

Sweet cottage in quiet convenient coastal setting.

ElizabethRating, 5 stars1 week ago
The property is tranquil and private but near convenient stores and food options. The cottage is so cute and quaint and was perfect for our stay with our dog. The art and small touches in the cottage are very lovely. This location is fantastic for accessing the beaches and harbors of York area.
Top Guest favourite
Cottage in Bridgton
4.9 out of 5 average rating, 240 reviews

Rustic Pebble Cottage in beautiful Bridgton, Maine

SandraRating, 5 stars3 weeks ago
This place has so much charm and makes you feel right at home. Cheryl baked cupcakes, put coffee, cream, milk, juice and Condiments as well as a well stocked kitchen and bathroom. I would highly recommend this cottage .
Guest favourite
Cottage in Windham
4.93 out of 5 average rating, 106 reviews

Cozy Cottage on Highland Lake

MeredithRating, 5 stars8 months ago
Perfect little Maine cabin getaway! We enjoyed our stay so much. The cabin was clean, easy to find, and had everything we needed for four people and two dogs. Cannot recommend enough!

Private cottage rentals

Guest favourite
Cottage in Ogunquit
5 out of 5 average rating, 30 reviews

Charming Coastal Cottage Ogunquit, ME

ChristineRating, 5 stars2 weeks ago
Kevin’s place was outstanding! Perfect location to walk to Main Street shopping and eateries (great ice cream place next door, too). Super clean and decorated really lovely. Loved having a second bathroom! Highly recommend!
Top Guest favourite
Cottage in Kennebunkport
4.99 out of 5 average rating, 67 reviews

Luxury KPort Cottage w/ private water access

KristinRating, 5 stars8 months ago
The perfect place to unwind and relax after a day spent exploring Kennebunkport! The cottage was super cozy, bed was comfortable and the hosts provided everything needed for an enjoyable stay! We would definitely stay here again. Thanks Dionne and Tim for sharing your lovely home!😊 Kristin & Kevin Dodson
Top Guest favourite
Cottage in Windham
5 out of 5 average rating, 80 reviews

Romantic waterfront cottage for two in Maine

DavidRating, 5 stars4 days ago
Perfect place to get away and relax. We enjoyed fishing in the morning and evening and sight seeing during the day. Quick trips into Portland, Kennebunkport, Freeport, and the Maine Botanical Gardens (highly recommended ). Locally we enjoyed the Maine Wildlife Park and u-pick strawberries. Picked up some wonderful seafood at Bob’s in Windham to cook in the well supplied kitchen. Mary Ellen and Brian have thought of the many little things that make the cottage a hospitable place. They answered our questions promptly leading up to our trip.
Top Guest favourite
Cottage in West Bath
4.92 out of 5 average rating, 77 reviews

Coastal Waterfront Tiny home in West Bath

LeahRating, 5 stars1 week ago
What an awesome airbnb! The views are stunning and surroundings couldn’t have been more peaceful. The cottage itself was exceptional and had everything I needed and more. Wish I could've stayed there longer! 10/10 would recommend this place to anyone!
Superhost
Cottage in York
4.84 out of 5 average rating, 31 reviews

Ocean View Cottage on Cape Neddick Beach

BarbaraRating, 5 stars1 week ago
We stayed at this property for 6 weeks with our dog and loved it. The neighborhood is gorgeous, walkable, and has the perfect beach for pup play. Owners are on-site, friendly, and quick to respond. The carriage house was very clean and as beautiful as pictured. We would certainly stay here again.
Superhost
Cottage in Waterboro
4.95 out of 5 average rating, 21 reviews

Quintessential Maine Lakefront Cottage.

LindaRating, 5 stars1 week ago
We were looking for a quiet place near the water to relax and unwind. Marina's place was perfect! We enjoyed kayaking, and great views of the lake whether reading on the deck or playing boardgames in the dining room on a rainy day. We'd definitely stay here again.
Top Guest favourite
Cottage in Biddeford
5 out of 5 average rating, 35 reviews

Secluded Coastal Home & Cottage 3 Minutes to Beach

BarbaraRating, 5 stars2 days ago
Thanks for a wonderful stay at your beautiful cottage! We were very comfortable and enjoyed sitting outside enjoying the quiet peaceful surroundings. Also, thanks for helping us out by supplying your personal baking pan so we could bake our brownies! We would definitely recommend your property to anyone looking for a house on the southern Maine coast. Barbara
Top Guest favourite
Cottage in Alton
5 out of 5 average rating, 35 reviews

Windswept Cottage: A Winnipesaukee Waterfront

SimonaRating, 5 stars7 months ago
The view is even more stunning in person! Spent the weekend here with my family and it was breathtaking to say the least. Half of our time was spent just admiring the view because it’s that good. Cozy decor and open floor plan made it easy to settle in and feel right at home. Peaceful private neighborhood with great foliage. Perfect place for getting out on the water in kayaks, making s’mores, stargazing, and creating life long memories. We wish we could’ve stayed longer!!

Destinations to explore

  1. Airbnb
  2. United States
  3. Maine
  4. York County
  5. Wells
  6. Drakes Island
  7. Cottage rentals