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Head of the Harbor- Nautical vacation rental in in walkable downtown with harbor view, grill & deck

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A wooden staircase with white railings leading to a covered porch. - Head of the Harbor- Nautical vacation rental in in walkable downtown with harbor view, grill & deck (Boothbay Harbor)
A modern living room with a glass coffee table, leather sofas, a round mirror, and artwork on the walls. - Head of the Harbor- Nautical vacation rental in in walkable downtown with harbor view, grill & deck (Boothbay Harbor)
A modern living room with a round mirror, a sofa, a coffee table, and a large window. - Head of the Harbor- Nautical vacation rental in in walkable downtown with harbor view, grill & deck (Boothbay Harbor)
A dining area with a wooden table, grey upholstered chairs, a chandelier, and a large abstract painting on the wall. - Head of the Harbor- Nautical vacation rental in in walkable downtown with harbor view, grill & deck (Boothbay Harbor)
A two-story house with a front porch, a staircase, and a driveway. - Head of the Harbor- Nautical vacation rental in in walkable downtown with harbor view, grill & deck (Boothbay Harbor)
Head of the Harbor- Nautical vacation rental in in walkable downtown with harbor view, grill & deck provides amenities like golfing on site and a garden. Stay connected with free in-room WiFi.

Reviews

2.0 out of 10

Entire home

4 bedrooms2 bathrooms1500 sq ft

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning
  • Outdoor Space

Add dates for prices

About this property

Head of the Harbor- Nautical vacation rental in in walkable downtown with harbor view, grill & deck

  • Retreat into the romance of coastal Maine at this exquisite Boothbay Harbor vacation rental that bursts with vintage character and seaside charm. Your harbor-view gem comprises two separate three-level homes. You'll love the antique decor and original 1800s wood floors, while modern amenities include updated kitchens and smart TVs. Across the street, you'll find sunset chairs with the best footbridge view in town. Stroll to the pier, waterfront parks, and tasty dining options. Pack your binoculars for Cap'n Fish's Whale Watching, climb aboard the Windjammer Eastwind, or rent a seafaring vessel at Schooner Eastward. Boothbay Harbor Country Club and Coastal Maine Botanical Gardens are within a short drive.

    Captain's Quarters' modern living area presents a Sonos system and a large 4K smart TV with access to Netflix, Hulu, Apple TV, and all of today's online entertainment. Prepare delicious dishes in the convenient full kitchen, configured with a small eat-in table and a larger nearby dining table.

    Sleep soundly in the primary suite that has an en suite bathroom that is also accessible via the hallway. One of the guest bedrooms includes a telescope for harbor gazing. All bedrooms provide a smart TV, bedside USB charging, and a Bluetooth music system.

    Head of the Harbor has an inviting living area with twin and queen sofa beds. The 4K smart TV provides access to Netflix, Hulu, Apple TV, and other services. A large farmhouse sink and an eat-in table highlight the beautifully updated kitchen. The gas grill on the deck is perfect for sunny afternoon cookouts. The bedroom occupies the entire top floor and features a charming antechamber with a window air-conditioning unit.

    Extra perks include complimentary commercial-grade WiFi and a backup generator. Each home is equipped with a private washer/dryer.

    THINGS TO KNOW
    The homes are not directly connected.

Property amenities

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

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

Bedrooms

  • 4 bedrooms
  • Bedsheets provided

Bathroom

  • 2 bathrooms
  • Shower
  • Towels provided

Living spaces

  • Living room
  • Separate dining area

Entertainment

  • Stereo
  • TV with cable/satellite channels

Outdoor areas

  • Barbecue grill
  • Garden

Laundry

  • Laundromat nearby
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • Near a hospital
  • Near the sea

Things to do

  • Golf
  • Birdwatching nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Hiking/biking trails nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Mountain biking nearby
  • Rafting nearby
  • Sailing nearby
  • Surfing/bodyboarding nearby
  • Swimming nearby
  • Water skiing nearby
  • Water tubing nearby
  • Whale watching 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

  • Garden
  • Unit size: 1,500 square feet

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Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in 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

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
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

About the neighborhood

Located in Boothbay Harbor, this vacation home is by the sea. Boothbay Region Land Trust and Boothbay Harbor Marina are worth checking out if an activity is on the agenda, while those in the mood for shopping can visit Boothbay Farmers' Market and Montsweag Flea Market. Coastal Maine Botanical Gardens and Opera House at Boothbay Harbor are also worth visiting. Discover the area's water adventures with jet skiing and kayaking nearby, or enjoy the great outdoors with hiking and cycling. Visit our Boothbay Harbor travel guide
View more Vacation 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 - 0.5 miles
  • Opera House at Boothbay Harbor
    3 min walk - 0.2 miles
  • Boothbay Region Land Trust
    8 min walk - 0.5 miles
  • Boothbay Harbor Memorial Library
    8 min walk - 0.5 miles
  • Burnt Island Living Lighthouse
    10 min walk - 0.6 miles

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
  • Tugboat Inn
    12 min walk
  • Footbridge Brewery
    7 min walk
  • The Thistle Inn
    4 min walk

Frequently asked questions

Is Head of the Harbor- Nautical vacation rental in in walkable downtown with harbor view, grill & deck pet-friendly?

No, pets are not allowed at this property.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Head of the Harbor- Nautical vacation rental in in walkable downtown with harbor view, grill & deck?

Check-in begins at 4:00 PM.

What time is check-out at Head of the Harbor- Nautical vacation rental in in walkable downtown with harbor view, grill & deck?

Check-out is at 10:00 AM.

Where is Head of the Harbor- Nautical vacation rental in in walkable downtown with harbor view, grill & deck located?

Situated by the sea, 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.

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Head of the Harbor- Nautical vacation rental in in walkable downtown with harbor view, grill & deck Reviews

Reviews

All reviews shown are from real guest experiences. Only travelers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
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Rating 10 - Excellent. 0 out of 1 reviews
Rating 8 - Good. 0 out of 1 reviews
Rating 6 - Okay. 0 out of 1 reviews
Rating 4 - Poor. 0 out of 1 reviews
Rating 2 - Terrible. 1 out of 1 reviews

8.0

Cleanliness

6.0

Location

Reviews

Verified

2/10 Terrible

Shannon B.

Liked: Cleanliness, check-in
Disliked: Communication, listing accuracy
While the stay was comfortable, there were too many other issues. Listing does not clarify that it is 2 separate units that do not connect. I was aware that there were 2 businesses also attached to the property. This wasn't an issue until we tried to park. Listing and check in instructions are not clear about where the driveway is located. Common sense dictated it would be the pull through driveway in the front of the property, but that was full of cars for the hair salon. All other parking in the lots around the side and back of the property have signs saying "You will be Towed". I called the number in the listing( this is a management co not the owner)and they weren't sure. So we left the property to go to dinner and when we got back the front driveway was empty so we parked there. Then in the morning the owner of the hair salon had blocked the driveway so we couldn't get the car out, came out of the salon to yell at us, then sent one of her employees out to accost us some more because the first time wasn't enough. All this was happening while I was trying to get answers from the people in charge of the property. Wasted a whole morning of my vacation dealing with this and waiting for them to call back(which didn't happen) I had to call them multiple times throughout the day. They did get the cars moved but no apology for the stress this caused. Property location is nice but there are too many other options to stay in the harbor. This one is not worth the hassle.
Stayed 3 nights in Jun 2026