
Cottage vacation 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.
Vacation 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

Freshly Renovated, Family-Friendly Coastal Cottage
A gem of an Airbnb! The hosts truly thought of everything and this was the perfect place to stay with two young kids; in fact, my son loved the bunkbed and toys so much he refused to go to bed every night! From the tonies box and kids toys, to all the beach and baby gear, there wasn’t one thing they lacked. The place was clean and organized and felt so cozy. I highly highly recommend this place, especially for families! The hosts were so friendly and accommodating as well.

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!

Beach Dreaming
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.

Paradise Found Minutes from Ogunquit | Heated Pool
Wow! What a beautiful place to stay. We visited all the surrounding cities we came to Maine for. The beds were so comfy! The towels smelled so fresh. The washer and dryer were so nice to have- so thoughtful that detergent was provided! We appreciated all the cute details the cottage had to offer. My girls loved the ride on the golf cart! 10/10 stay. Thank you so much for sharing your lovely place with us!

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

The Loon Nest, Waterfront Lake House, Wood Hot Tub
The house was clean and well maintained. The view was gorgeous, too bad Mother Nature didn’t cooperate. It was cold and rainy. Used the fire pit nightly and it was nice. Linens were clean, towels were soft and fluffy and smelled freshly laundered. Kitchen was spotless and well stocked with pot/pans and dishes. Having a dishwasher was nice too. Two grocery stores (Hannaford and Market Basket) were close by and plenty of restaurants too. We came with the intention of doing nothing and just changing scenery for the weekend. This place was perfect.

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

Bright, clean, private cottage near Higgins Beach!
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!

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!

Plum Island Sunset Cottage
We had a wonderful stay. 6 ladies coming together to celebrate a birthday,catch up on eachother's news, enjoy meals together by the sea, and relax. The setting and house were perfect for us. Spotlessly clean and cheerful, beautifully equipeed with extra everythings, well located close to the beach, the nature reserve and the center and surrounded by lovely views. The beds were comfy and the whole house felt like a longstanding part of the community yet newly renovated throughout and very welcoming. Amanda, our host, was warm and responsive and attentive to our needs. We'd be happy to return for another gettogether!

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.

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
Cheryl's home is cosy and quiet, and the photos don't quite do the place justice. It's an amazing spot since you can walk into town and access the trails to Pondicherry Park, and it's back off the road enough to feel private and quiet. We really enjoyed our stay, and especially the cupcakes that were there upon our arrival.

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

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!

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.

Seaside Serenity 2 - Oceanfront
We had a wonderful stay in Ogunquit! The views are AMAZING!! The space is very clean and exactly as described. So many great shops and restaurants right outside your door. Comfortable bed and great shower. It was a fun little getaway for me and my husband and our 3 month old.

Sleeps 10, 1.1 mi. to Beach, Fully Renovated 2025
Check in was a breeze, the house was clean and the beds were very comfortable. Close to Moody Beach and just a short drive to Ogunquit village. Would recommend staying here!

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.

Secluded Coastal Home & Cottage 3 Minutes to Beach
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!

Minnow Cottage in town, Kennebunkport
Fabulous location! Really couldn’t be any closer to downtown. Place was bigger than it looked in pictures. Super comfortable. Fabulous views!!

Appledore Cottage is a Family Vintage Cottage
We absolutely loved our visit to Appledore Cottage! It was quaint and perfectly relaxing. The screened in porch was the best place to just sit…very quiet and peaceful!
Destinations to explore
- China Vacation rentals
- Portland Vacation rentals
- Pocono Mountains Vacation rentals
- New York Vacation rentals
- East River Vacation rentals
- Hudson Valley Vacation rentals
- Plainview Vacation rentals
- Long Island Vacation rentals
- The Hamptons Vacation rentals
- Montreal Vacation rentals
- Boston Vacation rentals
- Québec City Vacation 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
- Brunswick Golf Club
- Cliff House Beach
- Palace Playland
- The Golf Club of New England
- Ferry Beach
- Funtown Splashtown USA