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Charming Maine cottage overlooking the working waterfront.

Waterfront cottage with kitchen and patio

Photo gallery for Charming Maine cottage overlooking the working waterfront.

Welcome to Drake Cottage! Here is the view of the house from the road.
Come enjoy the beautiful views of the harbor at Drake.
Grab your coffee or cocktail and sit outside.
Harbor views give Drake that real Maine feel.
Views for days!

Reviews

10 out of 10
Exceptional
1 bedroom1 bathroomSleeps 253.7 sq m

Popular amenities

  • Parking available
  • Kitchen
  • Outdoor space
  • Water view

Explore the area

View map
  • Place, Bowdoin College
  • Place, Bailey Island Bridge
  • Place, Popham Beach
  • Airport, Portland, ME (PWM-Portland Intl. Jetport)

Rooms & beds

1 bedroom (sleeps 2)

Bedroom

1 King Bed

1 bathroom

Bathroom

Toilet · Shower only

Spaces

Deck or patio
Kitchen
Dining area

About this property

Charming Maine cottage overlooking the working waterfront.

Welcome to Drake!

Looking for a romantic couple's getaway? This charming, newly remodeled one-bedroom cottage is located in the heart of Cundy's Harbor. Enjoy your morning coffee on the deck, that sits right over the water, while watching the lobstermen head out for their day.

Upon entering this adorable, quaint cottage you will first notice it's open concept living/kitchen area. The kitchen appliances are all smaller, including the fridge, but you can still utilize them for all your cooking needs. The bathroom is located on the first level and has a stand up shower. The sliding glass doors lead you right to the deck that sits out over the water. Upstairs you will find a large sized bedroom with a king size bed and beautiful ocean views.

*Note- the parking for the cottage is across the lawn.

Add dates for prices

Amenities

Kitchen
Outdoor space
Water view
Parking available

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House Rules

Check in after 4:00 PM
Minimum age to rent: 21
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher

About the area

Harpswell

Located in Harpswell, this cottage is in a rural area and on the waterfront. Gulf of Maine and Brunswick Golf Course are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Brunswick Town Commons and Cathance River Preserve. Paddleworks and Land's End Gift Shop are also worth visiting. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
View more Cottages in HarpswellOpens in a new window
Map
Harpswell, ME

What's nearby

  • Casco Bay - 1 min walk - 0.0 km
  • Bowdoin College - 23 min drive - 21.8 km
  • Bailey Island Bridge - 26 min drive - 21.5 km
  • LL Bean Flagship Store - 36 min drive - 41.2 km
  • Popham Beach - 58 min drive - 58.5 km

Getting around

  • Brunswick Station - 36 min drive
  • Wiscasset, ME (ISS) - 48 min drive

Restaurants

  • ‪Iris Eats Maine - ‬11 min drive
  • ‪Cook's Lobster House - ‬25 min drive
  • ‪Spinney's Restaurant - ‬49 min drive
  • ‪Gurnet Trading Company - ‬11 min drive
  • ‪Holbrooks Lobster Wharf - ‬19 min walk

Frequently asked questions

Is Charming Maine cottage overlooking the working waterfront. pet-friendly?

No, pets are not allowed at this property.

What time is check-in at Charming Maine cottage overlooking the working waterfront.?

Check-in begins at 4:00 PM.

What time is check-out at Charming Maine cottage overlooking the working waterfront.?

Checkout is at 10:00 AM.

Where is Charming Maine cottage overlooking the working waterfront. located?

Situated on the waterfront, this cottage is steps from Casco Bay and 2.6 mi (4.1 km) from Ragged Island. Brunswick Naval Aviation Museum and Thomas Point Beach are also within 12 miles (20 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 12 out of 13 reviews
Rating 8 - Good. 1 out of 13 reviews
Rating 6 - Okay. 0 out of 13 reviews
Rating 4 - Poor. 0 out of 13 reviews
Rating 2 - Terrible. 0 out of 13 reviews

10/10

Cleanliness

10/10

Check-in

9.6/10

Communication

9.8/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Charles F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Relaxing break on the coast

The cottage provided us the perfect base for relaxing with a cup of coffee in the morning or glass of wine at night.
Stayed 4 nights in Jun 2025

10/10 Excellent

Robin S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect spot in Harpswell. Cottage was lovely! Plenty of room for two. Spectacular sunsets and very peaceful. Enjoyed the harbor and traveling along the Maine coast. Truly a relaxing stay.
Stayed 7 nights in Sep 2025

10/10 Excellent

Kristen C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This property was great and amazing veiw and very peaceful. Its was the perfect place for the end of our trip.
Stayed 4 nights in Aug 2025

10/10 Excellent

Maggie T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful, Peaceful Views

We had a wonderful week. This cottage is nestled at the end of a quiet cove and quiet road. The house is perfect for two people. It sits right on the water, the view is lovely and peaceful. The bedroom is very comfortable, breezy and lovely views and sounds of gulls and boats. The kitchen was well equipped and had all we needed. We ate many meals on the outside table overlooking the water. The house is clean, comfortable- it made for a great home base to explore the area. I have fallen in love with the entire area.
Stayed 7 nights in Jul 2025

10/10 Excellent

Heidi Y.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Cottage for Two

The hubs and I booked the Drake as a “home base” as it’s sort of midway between day trips we wanted to take along the coast! The cottage, which the owner shared dates to the 1870’s, is beautifully refurbished, and while the fixtures and appliances are smaller than standard, they were more than adequate for us to store some food and prepare our meals and hold drinks, snacks and cocktails for on the deck each night. The fishing boats next door idled quietly out of the cove each morning. We heard them but were not disturbed in the least. Harpswell and Cundy’s Harbor are tiny but so picturesque. We drove to Lands End, walked down to Cedar Beach and collected a few shells and then ate THE BEST lobster roll I’ve EVER had at Sundrenched, right at the end of the Baily Island Bridge. We took day trips to Brunswick and Freeport for dinner and shopping, Bar Harbor, Acadia National Forest and Cadillac Mountain. We hiked the Ocean Trail in Acadia which was breathtaking and the Marginal Way in Ogunquit, took a lobstering excursion (highly recommend) and caught our own lobster lunch in Portland. We shot up to Bangor (Stephen King’s house) and hike the Oronco Bog Trail. We also spent a lazy day relaxing on Old Orchard Beach. Nothing was more than two hours away except for Bar Harbor/Acadia which was about three. But each time it was lovely to come back to this sweet spot for the evening! It was so quiet and peaceful - we highly recommend staying at the Drake!
Sunset from the deck at the Drake!
Lobster Lunch from Holbrook’s Harborside Grille
Stayed 7 nights in Jul 2025

10/10 Excellent

terrt a.

Liked: Cleanliness, check-in, communication, location, listing accuracy

60th birthday stay

We had such a great time. Just so relaxing and peaceful out there. waking up with a view of the ocean every day, has been incredible.
Stayed 4 nights in Jul 2025

10/10 Excellent

martin s.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fabulous

Our week at Drake cottage was beautiful, relaxing and much too short! The space and amenities are just right for two and exactly as advertised – the cottage and the location are just about as perfect as it gets. Time spent on the deck was a joy and the spaces inside, upstairs and down, managed to be both cozy and airy at the same time. The cottage was impeccably clean and outfitted, and Your Island Connection was consistently and immediately available if needed. We brought our sea kayaks with us and there was ample room to park the trailer and launching access was a very short carry down the end of the road. It was a wonderful week, and we are already planning and so looking forward to our next visit!
Stayed 7 nights in Aug 2022

10/10 Excellent

Luke D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful location, wonderful week

Drake Cottage was magical from start to finish. It was absolutely spotless when we arrived and everything in the rental is well thought out, comfortable and good quality. We loved our evenings on the deck, watching the sun going down over the harbor, watching the wildlife (have never seen so many herons) and particularly enjoyed watching the comings and goings of the lobster boats at the wharf. Wifi was excellent. Weather great - even the one rainy day - and I ate too many lobster rolls... ;D Truly a Maine experience and we cannot wait to come back. Thank you!
Stayed 7 nights in Jun 2022

10/10 Excellent

Beth T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Simply perfect

It was amazing! The cottage sat set to a working lobster wharf. We met and talked with the owner of the wharf. It was a perfect time for us.
Stayed 4 nights in Oct 2021

10/10 Excellent

Joe J.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Hidden Gem in Small Working Harbor

We loved our stay in this little cottage built out over Cundy's Harbor. Perfect size for a couple, it had everything we needed for a quiet week of relaxation, with the added bonus of a private deck facing west over the harbor. It's true that it is in a working harbor with a handful of lobster boats rumbling to life around 4:30 am, but it didn't really bother us. The only issue for us was the uncomfortable bed, which does need improvement, but we are already planning to return next year,
Stayed 7 nights in Jul 2021

8/10 Good

Debra M.

Liked: Cleanliness, check-in, location, listing accuracy

Cute

Quintessential Maine experience! Perfect for 2. Walk to the local store and docks. Close to hiking trails and close enough to Brunswick for great dinning!
Stayed 9 nights in May 2021

10/10 Excellent

Jill F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect, adorable cottage - gorgeous views!

Such a great cottage with a gorgeous view. Perfect for a couples retreat. We absolutely loved the view of the cove with the working lobsters boat. The sunsets were unbelievable and we made it a point to be back at the cottage so we never missed one. Very private, we stayed in October and the lobster boats were not noisy at all. Perfect location for us to see the sights in Bath, Brunswick, Bailey's Island, Freeport, Five Islands, Reid State Park. Boothbay Harbor was a short 50 min picturesque drive.
Stayed 7 nights in Oct 2020

10/10 Excellent

Nancy F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Restful Getaway

Drake Cottage was everything we expected and hoped for. The location makes for peace and quiet and the view of the harbor is lovely. The bedroom with it's king-sized bed and windows looking out to the water is pretty much perfect. It was truly a time of refreshment!
Stayed 4 nights in Sep 2020

About the host

Hosted by Your Island Connection, LLC

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