
Cottage holiday rentals in Drakes Island
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Top-rated cottage rentals in Drakes Island
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Popular amenities for cottage rentals in Drakes Island
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.

Cottage in Wells Maine
We had a wonderful stay here and highly recommend it! The location is great, as it’s close to plenty of restaurants and stores. We were even able to walk to get breakfast and dinner. The space itself was much larger than we expected and very clean. The kitchen had everything we needed and we even had snacks, waters, and coffee left for us! The highlight for my 2 year old was the pirate ship playground. We also loved having access to picnic tables. We got takeout and enjoyed eating outdoors. We did not use the outside grill but that is a great addition and we would have used if we stayed longer. The host was very helpful and accommodating. They offered early check in and check out and gave very clear instructions on how to get in. I would not hesitate to return in the future!

2 BR house, close to Ogunquit, w/ AC + golf cart!
Everything inside was so thoughtfully designed. Anything we needed was carefully labeled and placed where you might think it would be. The cottage was cozy, and very close to the main road leading to either Ogunquit or Wells. The welcome guide was detailed and informative. Plus we really appreciated our welcome message letting us know that it’s possible to see the northern lights during the night time.
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!

RK North : All season Waterfront cottage with dock
A Perfect Waterfront Escape – 5 Stars My wife and I had an unforgettable stay at RK North Waterfront Cottage. From the moment we arrived, we were welcomed by breathtaking views, fresh coastal air, and a sense of peaceful seclusion that made this trip truly special. The cottage itself was spotless, beautifully maintained, and tastefully decorated with cozy touches that made it feel like a true home away from home. We especially loved the spacious deck overlooking the water — perfect for morning coffee or evening wine while watching the sunset. The hosts were thoughtful and responsive, ensuring we had everything we needed without ever being intrusive. Whether it was relaxing by the fire pit, walking along the shore, or just enjoying the tranquility of the surroundings, every moment felt effortless and restorative. If you’re looking for a quiet getaway with charm, comfort, and stunning waterfront views, this is the place. We’re already planning our next visit. — Eric & Juliet DiNoto

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
We had such a great time staying at Emily's awesome retreat. It was our first mini-vacation with our dog and we were looking for some peaceful, wide open space to let her roam free. We absolutely got that with this home and thoroughly enjoyed the town, as well. Emily was super responsive whenever we did have a question and provided us with a great list of places to check out around town. Would absolutely stay again. Thanks!

Sweet cottage in quiet convenient coastal setting.
Lovely private location near beach, restaurants, and hiking. Donna provided great recommendations and timely responses. Would stay here again if in the area.

Lakefront, Beach Private, Amazing Views, & pets!
Helen was actually wonderful. She returned calls and everything. It was a great place to stay beautiful and hope to stay there again someday.
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

1 bedroom with pool, walk to the beach.
Best getaway for 2 sisters. We each had our own bed in a quiet area away from the street, but still very close to everything. The place was spotless, comfortable and so relaxing. Perfect location for access to the breakfast (across the street), dinner (next door) and Daddy's Homemade Icecream on the other side for dessert. So much to do, we had to get choosy. Neighbors are very welcoming as well. Thank you so much.

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!

Ocean view cottage, walk to Kennebunk Beach
This was our third year staying here. When I said that I wanted to return every year, I meant it! Katherine’s home is perfect for the three of us coming from various parts of the country and enjoying a once a year reunion. It is spotless and so comfortable with views of the ocean and lovely scenic walks right outside the door. Mother’s Beach is right around the curve in the road. We love it here! Until next year, thank you Katherine!

Sunny Beach Cottage / Sleeps 7 + Walk to the beach
The cottage was a perfect place to stay for our small family with a 3 year old. The location was in the middle of both beaches and downtown, about 15-20min walk to downtown center and 10min to the beach. With a small kid, we didn’t want to be in the busy dtown center so we didn’t mind walking or doing a short drive. We loved that the house came with beach gear (chairs, umbrella, towels, toys, and wagon), that saved us big time! The place was clean, cozy, had everything you need, and Elise was a great host that checked in and provided suggestions. Overall, we really enjoyed our stay and would recommend it!

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.

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.

Adorable Cottage Steps From Dock Square
Cute homey cottage, 10 min walk to bars and restaurants. Nice amenities, clean and comfortable!
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- Hampton Beach
- Ogunquit Beach
- Sebago Lake
- Wells Beach
- Scarborough Beach
- York Harbor Beach
- North Hampton Beach
- Weirs Beach
- Long Beach
- Popham Beach State Park
- Surfside Beach
- Crane Beach
- Long Sands Beach
- Good Harbor Beach
- Rye North Beach
- Brunswick Golf Club
- Bear Brook State Park
- Wentworth by the Sea Country Club
- East End Beach
- Palace Playland
- Ferry Beach
- Cliff House Beach
- King Pine Ski Area
- Purity Spring Resort