Charming, historic cottage with modern upgrades - stroll to dining & attractions

Top rated by guests
Exterior
Living area
Private kitchen
Private kitchen
Private kitchen
review stars
9.2Outstanding
(25 Ratings)
"Excellent location and very well maintained. Great WiFi."
Preston J.
Don't miss out! Price and availability may change
9.2 / 10
Outstanding(25 Ratings)

House in Boothbay Harbor, ME

8 guests · 3 bedrooms · 1 bath

Reasons to book

Guests love it hereGuests give this property a top rating
High-end valueWell priced for this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

About this house rental

Head of the Harbor II

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This luxury retreat in the heart of the Mid-Coast, Captain's Quarters, is an 1800s Boothbay Harbor cottage offering historic charm, modern furnishings, air-conditioning, and a prime locale looking directly out to the footbridge and across the street from the bay. A peaceful coastal getaway awaits, and you're only a short walk to the downtown shops and dining. You'll find a local brunch hot spot and a spa at your doorstep. When the day is done, head across the street to the sunset chairs providing the best view in town of the footbridge. Play golf or go sailing. Walk a half mile to Commercial Street and choose from whale watching at Maine Whale Watch, several great cruise operators, or renting a boat at Schooner Eastward.

Unwind into vacation mode in the modern living area. In the evening, listen to music on the Sonos system or settle in to stream a movie on the 55' 4k smart TV with access to Netflix, Hulu, Apple TV, and all of today's online entertainment. Prepare your favorite meals in the well-equipped kitchen, featuring an array of helpful appliances, including a dishwasher. Or, keep mealtime simple and sizzle burgers on the shared gas grill on the patio behind the building.

Each bedroom in this three-story home has a smart TV, bedside USB charging, and Bluetooth music systems. Find comfort in the primary suite, which has an en suite bathroom accessible via the hallway. A guest bedroom features a telescope for gazing out to the sites in the harbor.

Extra perks include a washer/dryer, complimentary commercial-grade WiFi, and a backup generator.

THINGS TO KNOW
This vacation rental is accessed via two steep flights of stairs.

Parking notes: There is free parking available for 2 vehicles.
This rental is located on floor 2.

Security camera details: this home is equipped with a ring door bell

Please note: this home resides in a noise-sensitive area and the owners participate in our Good Neighbor protection program. Our smart home technology will alert our team if excessive decibel or occupancy levels are detected, allowing us to reach out directly with a reminder of maximum occupancy and quiet hours. This technology is privacy compliant, and only monitors the presence of decibels and devices-not any personal conversation or information. Thank you for supporting our efforts to be good neighbors!

Damage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.
More information can be downloaded from the "Rental Agreement" on the checkout page.

Due to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

Amenities at Charming, historic cottage with modern upgrades - stroll to dining & attractions

Non-smoking
No pets allowed
Family friendly

Map of Boothbay Harbor, ME


Ratings and reviews

9.2 / 10
Outstanding(25 Ratings)
10 / 10Outstanding·Jul 2025
Excellent location and very well maintained. Great WiFi.
10 / 10Outstanding·Jul 2025
The upper apartment of the cottage was nice for our family of 5. Location is perfect to reach either side of the harbor within a 7 minute walk. The cafe downstairs is a town favorite but only takes cash. FYI. The steps inside the apartment to the third floor are extremely steep and shallow so be mindful if you have any older people or younger people that can’t easily navigate ladder-like stairs. The closet spaces within the upstairs rooms are very limited but there are dressers in each room with ample space to unpack.One note: There is no bathroom on the third floor where the 2/3 bedrooms are so if you have to wake up at night, it’s a steep climb down to the single bathroom and back up, in the dark! The kitchen appliances are very limited and utensils/kitchen dishes are sparse. This is a problem that needs attention. There was one cereal bowl in the whole house. - there is a Roku speaker that is nice to have for days you may be spending inside and a nice long table for puzzles and card games. Overall, the place is clean and has a lot of charm in the beautiful Boothbay setting.
10 / 10Outstanding·Oct 2023
This house is quaint and nicely furnished, in a great location to everything that’s happening in Boothbay Harbor!
6 / 10Average·Jun 2023
Stayed here for 3 nights with wife and in-laws. Listing doesn't do a very good job of telling you that the unit is not the building, but a smaller suite upstairs. Place was clean and updated. Kitchen had all of the bare essentials to do minor cooking (making breakfast was fine). One bedroom is on the main level, directly connected to the single bathroom. Other two bedrooms are up a VERY steep set of stairs that anyone that is not a child would struggle to use more than once. Doorframes on the upstairs units are also very low, anyone 6'2 or tall will easily bump their head unless they are actively avoiding it, as I did. Also, the price of the cleaning fee for this small of a place is absurd.

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FAQs

Is parking included with this house?

Parking is not specified as an available amenity at Charming, historic cottage with modern upgrades - stroll to dining & attractions. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.

Is Charming, historic cottage with modern upgrades - stroll to dining & attractions pet friendly?

Unfortunately, this house is not pet-friendly. Try searching again and filter for "Pets Allowed"

What amenities are available at Charming, historic cottage with modern upgrades - stroll to dining & attractions?

We found 3 amenities for this rental. This includes non-smoking, no pets allowed, and family friendly.