Entire home
Charming, historic cottage with modern upgrades - stroll to dining & attractions
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Reviews
9.2 out of 10
Wonderful
3 bedrooms 1 bathroom Sleeps 8 92.9 sq m
Popular amenities
Explore the area

Boothbay Harbor, ME
- Opera House at Boothbay Harbor3 min walk
- Boothbay Harbor Marina8 min walk
- Carousel Music Theater13 min walk
- Wiscasset, ME (ISS)32 min drive
Rooms & beds
3 bedrooms (sleeps 8)
Bedroom 1
1 Queen Bed
Bedroom 2
1 King Bed
Bedroom 3
2 Queen Beds
1 bathroom
Bathroom 1
Spaces
Deck or patio
Kitchen
Separate dining area
Dining area
About this property
Charming, historic cottage with modern upgrades - stroll to dining & attractions
Head of the Harbor II
Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'
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.
Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'
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.
Add dates for prices
Amenities
Kitchen
Washing machine
Dryer
Air conditioning
Outdoor space
Parking available
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House Rules
Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
No pets allowed
Smoking
Smoking is not permitted
Smoking is not permitted anywhere on the premises.
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, a first aid kit and a deadlock
About the area
Boothbay Harbor
Located in Boothbay Harbor, this holiday home is in the city centre and by the sea. Maine State Aquarium and Coastal Maine Botanical Gardens are local attractions and those in the mood for shopping can visit Boothbay Farmers' Market and Montsweag Flea Market. Boothbay Railway Village and Dolphin Mini Golf are also worth visiting. Make sure you get close to the area's animals with activities such as game walks and birdwatching.

Boothbay Harbor, ME
What's nearby
- Opera House at Boothbay Harbor - 3 min walk - 0.3 km
- Boothbay Region Land Trust - 6 min walk - 0.6 km
- Boothbay Harbor Marina - 8 min walk - 0.7 km
- Burnt Island Living Lighthouse - 10 min walk - 0.9 km
- Carousel Music Theater - 13 min walk - 1.1 km
Getting around
Restaurants
- Circle K - 14 min walk
- Tugboat Inn - 12 min walk
- Pinkham’s Gourmet Market - 2 min drive
- The Thistle Inn - 4 min walk
- Dunton's Doghouse - 15 min walk
Frequently asked questions
About the host
Hosted by Vacasa of Maine

Languages:
English, French, German, Italian, Spanish
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