
Cottage holiday rentals in Drakes Island
Find and book unique cottages on Airbnb
Top-rated cottage rentals in Drakes Island
Guests agree: These cottages are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Drakes Island cottage rentals
Cottage rentals with a hot tub

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!

Freshly Renovated, Family-Friendly Coastal Cottage
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!

Paradise Found Minutes from Ogunquit | Heated Pool
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!

Fully Renovated/4min to K-port/HotTub/Game Room
Great clean air bnb. Accurately as described.. looks good in photos but even better in-person. Bed was comfortable. Would rent their properties again.

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

The Loon Nest, Waterfront Lake House, Wood Hot Tub
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.

Contemporary Cottage With Ocean View 13
Great place! Very cute home with very communicative hosts.

Cottage in Wells Maine
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

Salty Mermaid Cottage/Boat House
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.

Lovely cottage on Sunrise Lake, Middleton, NH.
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!

Cozy Cottage by the Sea
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.

Sunset Haven - Little Sebago Lake
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.

True Maine Artist Cottage with Outdoor Shower
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.

Sweet cottage in quiet convenient coastal setting.
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.

Rustic Pebble Cottage in beautiful Bridgton, Maine
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 .

Cozy Cottage on Highland Lake
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

Luxury KPort Cottage w/ private water access
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

250 feet from beach sand! 2 bedroom cottage
cannot beat the price for the location and size. host was great, this was my first Airbnb stay and he made it easy. finding a two bedroom within walking distance to the beach at this price is crazy.

Romantic waterfront cottage for two in Maine
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.

Ocean View Cottage on Cape Neddick Beach
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.

Quintessential Maine Lakefront Cottage.
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.

Secluded Coastal Home & Cottage 3 Minutes to Beach
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

Windswept Cottage: A Winnipesaukee Waterfront
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!!

Minnow Cottage in town, Kennebunkport
This home was lovely and in a great location for our trip to the Preludes. Brian was a great host and we would love to stay here again!
Destinations to explore
- China Holiday rentals
- Portland Holiday rentals
- Pocono Mountains Holiday rentals
- New York Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Plainview Holiday rentals
- Long Island Holiday rentals
- The Hamptons Holiday rentals
- Montreal Holiday rentals
- Boston Holiday rentals
- Québec City Holiday rentals
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Hampton Beach
- Ogunquit Beach
- Sebago Lake
- Wells Beach
- Scarborough Beach
- York Harbor Beach
- North Hampton Beach
- Weirs Beach
- Popham Beach State Park
- Long Beach
- Surfside Beach
- Crane Beach
- Long Sands Beach
- Good Harbor Beach
- Rye North Beach
- Bear Brook State Park
- Wentworth by the Sea Country Club
- East End Beach
- Cliff House Beach
- Brunswick Golf Club
- Palace Playland
- The Golf Club of New England
- Funtown Splashtown USA
- Ferry Beach