Entire home

Head of the Harbor II- Historic cottage with modern upgrades - stroll to dining & attractions

Photo gallery for Head of the Harbor II- Historic cottage with modern upgrades - stroll to dining & attractions

A wooden staircase with white railings leading to a covered porch. - Head of the Harbor II- Historic cottage with modern upgrades - stroll to dining & attractions (Boothbay Harbor)
A dining area with a wooden table, chairs, a chandelier, and a large mirror. - Head of the Harbor II- Historic cottage with modern upgrades - stroll to dining & attractions (Boothbay Harbor)
A spacious living area with a sofa, coffee table, and dining table. - Head of the Harbor II- Historic cottage with modern upgrades - stroll to dining & attractions (Boothbay Harbor)
A two-story building with a porch, a sign for 'Mama's Cafe,' and an ATM. - Head of the Harbor II- Historic cottage with modern upgrades - stroll to dining & attractions (Boothbay Harbor)
A modern living room with a round mirror, a sofa, a coffee table, and a large window. - Head of the Harbor II- Historic cottage with modern upgrades - stroll to dining & attractions (Boothbay Harbor)
Located close to Coastal Maine Botanical Gardens, Head of the Harbor II- Historic cottage with modern upgrades - stroll to dining & attractions has plenty to offer. Stay connected with free in-room WiFi.

Reviews

9.2 out of 10
Wonderful

Entire home

3 bedrooms1 bathroom93 sq m

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning
  • Parking available

Add dates for prices

About this property

Head of the Harbor II- Historic cottage with modern upgrades - stroll to dining & attractions

  • Captain's Quarters | Historic Coastal Luxury in the Heart of Boothbay Harbor

    Experience the perfect blend of historic New England charm and modern luxury at Captain's Quarters, a beautifully restored 1800s cottage nestled in the heart of Boothbay Harbor. Overlooking the iconic footbridge and located directly across from the harbor, this elegant retreat offers a front-row seat to one of Maine's most beloved coastal destinations.

    Step outside and immerse yourself in the vibrant harbor atmosphere. Downtown shops, restaurants, galleries, and waterfront attractions are just a short stroll away. Enjoy a leisurely brunch at a local favorite, indulge in a relaxing spa treatment nearby, or take in the spectacular harbor sunsets from the Adirondack chairs located across the street. For adventure seekers, golf courses, sailing excursions, whale-watching tours, harbor cruises, and boat rentals are all within easy reach.

    Inside, the home seamlessly combines classic architecture with contemporary comforts. The inviting living area is designed for relaxation, featuring comfortable furnishings, a Sonos sound system, and a 55-inch 4K Smart TV with access to Netflix, Hulu, Apple TV, and other popular streaming services.

    The well-appointed kitchen makes meal preparation a pleasure, offering modern appliances, ample workspace, and a dishwasher for easy cleanup. Guests may also enjoy the shared outdoor patio area with a gas grill, perfect for casual summer cookouts.

    Spanning three levels, each bedroom is thoughtfully equipped with its own Smart TV, Bluetooth music system, and convenient USB charging stations. The primary suite offers a peaceful retreat with access to a private en-suite bathroom. One guest bedroom even features a telescope, allowing guests to enjoy harbor views and stargazing from the comfort of the home.

    Additional amenities include:

    Central air conditioning
    Commercial-grade high-speed WiFi
    Washer and dryer
    Sonos whole-home audio system
    Backup generator
    Smart TVs throughout the home

    Whether you're exploring the waterfront, setting sail on the harbor, enjoying fresh Maine seafood, or simply relaxing while watching boats pass by, Captain's Quarters offers an unforgettable Boothbay Harbor experience.

    Things to Know
    This vacation rental is accessed by two steep flights of stairs and may not be suitable for guests with mobility limitations.
    The outdoor gas grill and patio area are shared with neighboring guests.
    Convenient walking access to downtown Boothbay Harbor, waterfront attractions, dining, shopping, and excursion departures.

Property amenities

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Microwave
  • Oven
  • Refrigerator

Bedrooms

  • 3 bedrooms
  • Bedsheets provided

Bathroom

  • 1 bathroom
  • Hair dryer
  • Shower
  • Towels provided

Living spaces

  • Fireplace
  • Separate dining area

Entertainment

  • Books
  • Stereo
  • TV with cable/satellite channels

Outdoor areas

  • Barbecue grill

Laundry

  • Laundromat nearby
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • In a village
  • In the city centre
  • Near a hospital
  • Near the sea

Things to do

  • Birdwatching nearby
  • Cycling nearby
  • Ecotours nearby
  • Fishing nearby
  • Hiking/biking trails nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Parasailing nearby
  • Sailing nearby
  • Scuba diving nearby
  • Snorkelling nearby
  • Surfing/bodyboarding nearby
  • Swimming nearby
  • Water skiing nearby
  • Water tubing nearby
  • Whale watching nearby
  • Wildlife walks nearby
  • Winery tours nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • First aid kit
  • Fire extinguisher
  • Deadbolt lock

General

  • Unit size: 1,000 square feet

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Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in and check-out are available
Minimum check-in age - 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

Pets not allowed

Children and extra beds

Children are welcome
Note from host: Children allowed

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with EU regulations about consumer rights, property booking services are not subject to the right of withdrawal.

About the area

Located in Boothbay Harbor, this holiday home is in the city centre and by the sea. Boothbay Region Historical Society Museum and Boothbay Harbor Memorial Library are local landmarks, and travellers looking to shop may want to visit Boothbay Farmers' Market and Montsweag Flea Market. Coastal Maine Botanical Gardens and Opera House at Boothbay Harbor are also worth visiting. Jet skiing and kayaking offer great chances to get out on the surrounding water, or you can seek out an adventure with ecotours and hiking nearby. Visit our Boothbay Harbor travel guide
View more Holiday homes in Boothbay Harbor
Map
Boothbay Harbor, ME

What's nearby

  • A harbor with boats, a dock, and a rocky shoreline with a lobster trap.
    Boothbay Harbor Marina
    8 min walk - 0.7 km
  • A picnic table by a river with a stone wall and trees.
    Barrett Park
    11 min walk - 1.0 km
  • Opera House at Boothbay Harbor
    3 min walk - 0.3 km
  • Boothbay Region Land Trust
    8 min walk - 0.7 km
  • Burnt Island Living Lighthouse
    10 min walk - 0.9 km

Getting around

  • Brunswick Station
    46 min drive
  • Wiscasset, ME (ISS)
    27 min drive

Restaurants

  • Coastal Maine Botanical Gardens
    7 min drive
  • Circle K
    14 min walk
  • Kitchen Garden Cafe
    7 min drive
  • Boothbay Lobster Wharf
    11 min walk
  • Tugboat Inn
    12 min walk

Frequently asked questions

Is Head of the Harbor II- Historic cottage with modern upgrades - stroll to dining & attractions pet-friendly?

No, pets are not allowed at this property.

How much is parking at Head of the Harbor II- Historic cottage with modern upgrades - stroll to dining & attractions?

On-site parking is available at the property.

What time is check-in at Head of the Harbor II- Historic cottage with modern upgrades - stroll to dining & attractions?

Check-in begins at 4:00 PM.

What time is check-out at Head of the Harbor II- Historic cottage with modern upgrades - stroll to dining & attractions?

Checkout is at 10:00 AM.

Where is Head of the Harbor II- Historic cottage with modern upgrades - stroll to dining & attractions located?

Located in the heart of Boothbay Harbor, this holiday home is within a 10-minute walk of Opera House at Boothbay Harbor, Boothbay Region Historical Society Museum and Boothbay Region Land Trust. Boothbay Harbor Marina and Fisherman's Memorial Park are also within 10 minutes.

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Reviews

Head of the Harbor II- Historic cottage with modern upgrades - stroll to dining & attractions Reviews

9.2

Wonderful

9.6

Cleanliness

10

Location
Rating 10 - Excellent. 18 out of 27 reviews
Rating 8 - Good. 7 out of 27 reviews
Rating 6 - Okay. 2 out of 27 reviews
Rating 4 - Poor. 0 out of 27 reviews
Rating 2 - Terrible. 0 out of 27 reviews

Reviews

From a partner site

10/10 Excellent

Charming

This house is quaint and nicely furnished, in a great location to everything that’s happening in Boothbay Harbor!
Stayed 5 nights in Oct 2023
From a partner site

10/10 Excellent

Cozy and beautiful home

Loved this beautiful property. Quiet, well maintained, clean and private. Close to the botanical gardens and a country store. We used the house canoe to row to the country store for coffee. The house is beautiful
From a partner site

10/10 Excellent

Cozy home above a charming coffee shop. What more could you ask for?

We loved this property! So comfy and cozy. Furniture all very inviting and beds and bedding were great. We loved walking downstairs in the morning to have coffee and a delicious breakfast at MaMa D’s coffee shop. The cutest place. We would definitely book here again. Great value!
Stayed 3 nights in Sep 2023
Verified review

10/10 Excellent

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

Nice property with excellent location, with a few caveats

Check in was super smooth and the house location was excellent with off street parking. Conveniently located in town, and also half way between Southport Island and East Boothbay areas, while being right on the north edge of town for easy access to leave the Boothbay area for day trips to Freeport, Bath, Rockland, Bar Harbor, etc. The interior decor is well themed and the three bedrooms are very comfortable. Modern electrical and amenities throughout, between the lighting and the televisions to Wi-Fi and HVAC. The living area and dining areas are very spacious and make for a very relaxing and comfortable stay for a larger family. Now for some of the concerns we had throughout our stay: there is only one bathroom on the main floor (second story of building) this required a bit more coordination during the stay. Not a deal breaker, but something to keep in mind. The hardwood floors are very smooth, and the edges are not well sanded; house slippers are a must otherwise there are some risks of snags on socks or worse a splinter in the foot. The stairs are also very steep, and smooth. This presents a slip hazard that really should be addressed with some traction tape at the edge of each stair tread. Hold the handrail firmly when using the stairs! Lastly, the breakfast cafe on the ground floor of the building has outdoor seating in the back of the house. If you are a late sleeper or plan to leave windows open through the night and into the morning be prepared for conversation noise
Stayed 6 nights in Sep 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location, very clean, perfect for out trip!
Stayed 3 nights in Jun 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent location and very well maintained. Great WiFi.
Stayed 4 nights in Jul 2025
Verified review

8/10 Good

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

Great location

Clean and cute. Excellent location
Stayed 3 nights in Apr 2022
Verified review

10/10 Excellent

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

Boothbay Getaway

Very accurately described property. We enjoyed the stay and location. Many restaurants within walking distance. Everything was clean and fresh. Would not recommend for elderly, steps are steep.
Stayed 4 nights in Oct 2021
Verified review

10/10 Excellent

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

great location

Very nice property. there could be a couple improvements that could make it fantastic, like hangers and a second AC unit top floor, hooks in bathroom for towels or robes. There were clean beds, nice pillows and plenty of towels.
Stayed 5 nights in Jul 2022
Verified review

10/10 Excellent

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

Great Location and Home

This property was in an ideal location near the harbor. It was over a restaurant which did not impact daily functions and created an additional fun feature. There was ample space for a family of six and was very well maintained.
Stayed 4 nights in Jul 2022
Verified review

8/10 Good

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

Right in the harbor!

Very steep stairs
Stayed 7 nights in Oct 2022
From a partner site

10/10 Excellent

Mr. Telon

Beautifully decorated and comfy home with water views and walking distance to town. Very relaxing.
Verified review

10/10 Excellent

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

Beautiful place, great location!

We loved everything about this place! We were reluctant to book a new place without previous reviews, but we’re glad we did! It is just as described with a large living / dining space, many conveniences such as USB bedside chargers, premium decor and the view looks right over the harbor and footbridge. The location is ideal just 5 minutes from downtown and with the best breakfast place right at the doorstep. We’re excited to go back over the summer when the town is fully open!
Stayed 3 nights in Mar 2021
From a partner site

10/10 Excellent

Wonderful get a way for families

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We had our adult children on vacation with us and everyone had their own room which was a perfect arrangement for sleeping. The decor was lovely, beds comfortable and location wonderful!
From a partner site

10/10 Excellent

Beautiful property, excellent location

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We loved our stay here! The home is beautifully decorated and impeccably clean. We were so well taken care of during the week, and the location can’t be beat. Quiet neighborhood with easy walking access to town.
Verified review

10/10 Excellent

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

Fantastic stay, amazing views and location!

Amazing location and property. Walking distance to all of the downtown restaurants and bars in Boothbay. Having a coffee shop downstairs was super convenient. Apartment was beautiful, very clean, modern, and had everything we needed. We were a bit nervous about booking a place that only had one review, but we're so happy we did. Management was very easy to communicate with, instructions were clear, and we had no issues during our stay. We'll be back!
Stayed 3 nights in May 2021
From a partner site

10/10 Excellent

Fantastic

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Excellent location, very clean. Highly recommended
Verified review

8/10 Good

Liked: Check-in, communication, location, listing accuracy

Excellent location, watch out for the stairs

The location is perfect- walkable to the main area of town and above a fantastic breakfast spot. The unit is well-maintained and nicely furnished, although it could have been a little cleaner at check-in. The main red flag is the stairs (both floors but especially to the third floor). They are steeply pitched and challenging to descend.
Stayed 3 nights in Aug 2022
Verified review

6/10 Okay

Liked: Cleanliness, check-in, communication, location

Good Location, Adequate Amenities, But beware stairs and low doorframes

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.
Stayed 3 nights in Jun 2023
From a partner site

8/10 Good

Nice location.

The location in Boothbay Harbor and the town itself are great. The home is spacious, at least if you do not have too many people trying to share the one bathroom. It was nice and clean. Aspects that were less than desirable were the lack of almost any pantry items needed for cooking, such as some basic spices (other than salt and pepper), oils, etc. We had planned to cook Thanksgiving dinner, which would have been possible with the pots and pans, but we would have had to stock the kitchen with basic pantry items to really cook. We also had to purchase a lobster cracker in order to cook and eat a lobster. Finally, none of the beds had pillows we could sleep on; while they look nice for a made bed, they are all huge and very uncomfortable to sleep on. I felt like I was wrangling a small cow in order to try to squish a pillow into a position I could sleep on; they are firm and about 1 feet high and 3 feet long, which is perfect for a giant but not most ordinary humans.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 4 nights in Jun 2025
Verified review

8/10 Good

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

Beautiful with great location, maybe haunted

We had a great time on our trip! Snug Harbor was beautiful, cozy, had everything we needed, and an excellent view of BBH! Minor concern was we weren't sure which sunset chairs were ours to sit in. There was some construction across the street so not sure we could have even made it to the chairs if we knew which ones to use. We joked through out the trip that the place was maybe haunted as we constantly heard suspicious sounds day or night. A major issue that we had is a stranger unlocked the door and walked right up into the living area at 8:00 a.m. while we were in our pajamas. There was concern that our shower was leaking into Mama D's cafe and the owner sent him to check it out. After multiple phone calls on our end to figure out what was going on, it does sound like it was an honest mistake that the owner thought our unit was empty. However, a stranger walked in on 3 young females not fully dressed, nobody told us if we could continue using the shower, was a plumber coming, did we need to leave the house, etc.
Stayed 4 nights in May 2023
Verified review

10/10 Excellent

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

Great Location

Location was great for easy driving to many destinations & had a beautiful view of Boothbay Harbor & the bridge which was so pretty at night. It was mostly clean. I did spot what looked like makeup from a previous guest on bathroom floor & I tried to clean it up but it just smeared. The upstairs Captain's Quarters room looks like it had a new window ac but the cord was too short to plug in. Luckily our son had a short extension cord with him otherwise it would have been too hot upstairs. The only 2 things we thought would have been nice were a toaster & an exhaust fan in the bathroom. Otherwise the layout of the apartment was perfect. Tv's had good viewing choices & all the furniture was comfortable. There was plenty of towels & the kitchen was well stocked (except for missing toaster) Would advise people to be aware that it it a bit noisy in the morning with the cafe next door (which was not a problem for us) & the stairs are kind of on the steep side and there are 2 sets of stairs. We would love to stay here again.
Stayed 4 nights in Aug 2021
From a partner site

8/10 Good

Cozy and Quirky with Ocean View

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Three generations of our family spent 4 happy days in this cozy, quirky, retreat in Boothbay Harbor. The place definitely met our space and charm requirements, with 3 large bedrooms, large dining table, and comfy, attractive furnishings. Located above a popular breakfast/lunch restaurant, steps from the ocean, the unit is within easy walking distance to shops and eateries, and is generously equipped with towels, linens, blankets, dishes, cutlery and tv’s. I highly recommend this charming apartment, with the following caveats:1. Expect two steep flights of stairs and narrow treads. FYI: think Amsterdam. 2. I expected only 1 bathroom, but the 1 roll of tp was a surprise. It would be helpful to have extra rolls in the bathroom cabinet.3. One upstairs bedroom has 3 fans and 3 windows, but no AC. 4. The other upstairs bedroom has an AC unit, but the cord is a few inches short of the outlet. If visiting during summer, pack a utility cord.5. Mattresses are compfy but pillows are extremely firm. If you need some flex, consider bringing a pillow.6. Space to hang clothes is ample, but if hangers are required, bring them.
From a partner site

8/10 Good

Boothbay Beauty

The home was built in the late 1800’s which means you’ll find lots of character here. The downside is that the 2 sets of stairs are not to today’s standards and are very steep with tiny treads making them difficult to maneuver. Note that there is only one bathroom for the 3 bedrooms. The accommodations were very nice and relaxing and the home is equipped with very good tvs. Currently there is a beautiful view of the harbor out the windows but that’ll be disappearing as soon as the home being built across the street goes up. We did not have two reliable parking spaces, at best only one my, because someone at the hair salon next door kept parking their very large truck in the spot reserved for those renting this unit. There is noise in the morning in the master bedroom because it’s window looks out over the patio belonging to the breakfast restaurant housed in the first level of the home. We enjoyed Mana D’s, the restaurant in the home, but light sleepers may find the noise problematic in the morning. The noise was only from the patio though, not from the restaurant itself. The bathroom was fine and hot water was not an issue, and the kitchen worked well for our needs. My complaints would be the 2 dangerous stairways, the parking situation, the lack of hangers in each closet, and the blinds on the windows weren’t room darkening so it was bright in the morning in a couple of the bedrooms and the living room. The location of the house is excellent. It is a 10 minute walk, or less, into the heart of the historic downtown area and there are restaurants, galleries and shops on the way. The rental has beautiful furnishings and is well maintained and is very comfortable. I would absolutely considering staying in this rental again but if you have any travelers who have issues with stairs, especially very steep stairs, I would not recommend staying here.