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

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Exterior
Living area
Living area
Living area
Dining

Reviews

9.2 out of 10
Wonderful
3 bedrooms1 bathroomSleeps 81000 sq ft

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Air conditioning
  • Outdoor Space
  • Parking available

Explore the area

View in a map
Boothbay Harbor, ME
  • Place, Opera House at Boothbay Harbor
    ‪3 min walk‬
  • Place, Boothbay Region Land Trust
    ‪6 min walk‬
  • Place, Boothbay Harbor Marina
    ‪8 min walk‬
  • Airport, Wiscasset, ME (ISS)
    ‪31 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 prices include all fees. No hidden fees.

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
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
Smoking is not permitted anywhere on the premises.
For information about quiet hours, please refer to the listing description.

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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock

About the neighborhood

Boothbay Harbor

Located in Boothbay Harbor, this vacation home is in the city center and by the sea. Opera House at Boothbay Harbor and Maine State Aquarium are local attractions and those in the mood for shopping can visit Boothbay Farmers' Market and Montsweag Flea Market. Coastal Maine Botanical Gardens and Boothbay Railway Village are also worth visiting. Discover the area's water adventures with jet skiing and kayaking nearby, or enjoy the great outdoors with ecotours and cycling.
View more Vacation Homes in Boothbay HarborOpens in a new window
Map
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
  • Boothbay Harbor Memorial Library - 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

  • ‪Circle K - ‬14 min walk
  • ‪Pinkham’s Gourmet Market - ‬2 min drive
  • ‪Dunkin' - ‬3 min drive
  • ‪Harborside 1901 Bar & Grill - ‬8 min walk
  • ‪Tugboat Inn - ‬12 min walk

Frequently asked questions

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

No, pets are not allowed at this property.

How much does it cost to stay at Charming, historic cottage with modern upgrades - stroll to dining & attractions?

As of Apr 5, 2026, prices found for a 1-night stay for 2 adults at Charming, historic cottage with modern upgrades - stroll to dining & attractions on May 6, 2026 start from $262, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Charming, historic cottage with modern upgrades - stroll to dining & attractions?

Check-in begins at 4:00 PM.

What time is check-out at Charming, historic cottage with modern upgrades - stroll to dining & attractions?

Check-out is at 10:00 AM.

Where is Charming, historic cottage with modern upgrades - stroll to dining & attractions located?

Located in the heart of Boothbay Harbor, this vacation 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 Boothbay Harbor Memorial Library are also within 10 minutes.

Reviews

9.2

Wonderful

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 16 out of 25 reviews
Rating 8 - Good. 7 out of 25 reviews
Rating 6 - Okay. 2 out of 25 reviews
Rating 4 - Poor. 0 out of 25 reviews
Rating 2 - Terrible. 0 out of 25 reviews

9.6/10

Cleanliness

10/10

Check-in

9.4/10

Communication

10/10

Location

9.4/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Preston J.

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

10/10 Excellent

Mary W.

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

June D.

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

10/10 Excellent

Gaby K.

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
Verified

10/10 Excellent

Juliet J.

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

6/10 Okay

Ryan O.

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
Verified

8/10 Good

Andrea W.

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

10/10 Excellent

Elton W.

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
From a partner site

8/10 Good

William W.

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.
From a partner site

6/10 Okay

Guay J.

Les lits sont confortables et propres. Aussi la maison est bien située par rapport au cent...

Les lits sont confortables et propres. Aussi la maison est bien située par rapport au centre-ville. Les serviettes étaient suffisantes. La maison est accueillante et la décoration est belle. Cependant il y a des manquements dans la cuisine: coupes à vin seulement 2,pas de grille-pain,pas de napperons,le four pas nettoyé. Pour un groupe de 5 il a manqué de papier de toilette et aucun papier mouchoir est fourni. Il n’y a aucun cintres et crochets dans les chambres
Stayed 3 nights in Sep 2022
From a partner site

8/10 Good

Coleen P.

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

8/10 Good

Cathy F.

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

Right in the harbor!

Very steep stairs
Stayed 7 nights in Oct 2022
Verified

8/10 Good

Ian C.

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

10/10 Excellent

Brenda M.

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

10/10 Excellent

Mike T.

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

8/10 Good

David C.

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

Great location

Clean and cute. Excellent location
Stayed 3 nights in Apr 2022
From a partner site

10/10 Excellent

CHARLES N.

Mr. Telon

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

10/10 Excellent

Brandi R.

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
From a partner site

8/10 Good

jennifer g.

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.
Verified

10/10 Excellent

Diane P.

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

10/10 Excellent

coleen n.

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

Nichole M.

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.
From a partner site

10/10 Excellent

Martin B.

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
From a partner site

10/10 Excellent

Martin B.

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

10/10 Excellent

Michael C.

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

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