Vacation Rentals By Owner In Boothbay Harbor, ME

$289.58

Coastal downtown 1 Bed, 1 Bath, full kitchen w/ harbor view

Boothbay Harbor, Maine, United States

Located in the heart of downtown Boothbay Harbor, you'll be entranced by views of lobster fisherman returning to the wharf. Spend a warm summer day exploring the quaint gift shops and enjoy some of Maine's best seafood. Hop on a harbor cruise to catch sight of whales, seals, lighthouses and puffins.brThe spacebrThe Coastal Cottage Suite is a one bedroom, one bathroom suite with attached living room. You will enter through a private entrance, up one flight of stairs. A private galley kitchen is included where you can prepare your own meals. This Suite is decorated in serene blue and beige decor to relax you after a long day of sightseeing, hiking, or kayaking. There are stunning water views of Boothbay Harbor from both the bedroom and living room.brbrbrThis suite sleeps two people and is outfitted with a queen size bed. The living room is equipped with Roku and WIFI is included. There is one parking spot provided; street parking is limited to two hours. The backyard is shared with the adjacent units, which may be occupied during your stay.brGuest accessbrLocated in the back of the building is a private entry up one flight of stairs to yellow door #1. Parking is on the right side of the driveway, pull in at an angle.brOther things to notebrA short ten minute drive away is renowned Coastal Maine Botanical Gardens, you’ll be enchanted by the beautiful foliage and troll sculptures. Ask your hosts, Steve and Julie, for assistance in booking a trip to Cabbage Island for a clambake. There are over 30 restaurants and coffee shops within walking distance for you to enjoy.brbrbrThe Coastal Cottage Suite is located at 53 Commercial Street, Boothbay Harbor, Maine 04538, next to Ports of Italy, and three blocks from the Footbridge.

1

Bed

1

Bath

2

Sleeps

$566.59

/ Nightly

Private Vacation Home

Classic New England Retreat in the Heart of Boothbay Harbor

Boothbay Harbor, Maine, United States

Discover refined coastal living just a two-minute walk from the water in this thoughtfully restored New England colonial. Blending historic architectural details—including antique radiators and classic penny mosaic tile baths—with modern comforts including high-speed internet and fully fenced in back yard. This bright and cheery home offers an elegant and relaxing home base for any season.brbrInside, the home is designed for comfort and ease. The well-appointed kitchen features thoughtful touches for home-cooked meals, while the living area offers a polished setting to unwind with a wet bar, streaming-ready TV, and Fidium high-speed internet. Mini-split systems provide quiet, efficient heating and cooling year-round, and a private washer and dryer add everyday convenience. brbrOutdoor spaces invite relaxation, from mornings in Adirondack chairs on the deck to evenings enjoying s’mores around the fire pit. A fenced yard provides a private, secure space for children or one well-behaved dog (up to 50 lbs).brbrSpend your days exploring Boothbay Harbor’s working waterfront, boating along the coast, and dining at acclaimed local favorites. Enjoy the convenience of walking to Atlantic Edge for fresh lobster or the Boothbay Lobster Wharf for lunch or dinner. The home is also ideally situated near the Coastal Maine Botanical Gardens (including the renowned Gardens Aglow winter display), Boothbay Harbor Country Club, and Hendricks Head Beach.brbrImportant Informationbrbr-Streaming services require guest loginsbrbr-One dog permitted (up to 50 lbs)brbr-Parking available for up to three vehiclesbrbr-The fireplace is decorative and not intended for usebrbrMinimum renter age: 25brbrThis well-maintained and peaceful cottage offers a seamless balance of walkable convenience, understated luxury, and timeless Maine charm—an ideal retreat for discerning travelers seeking comfort, privacy, and an authentic coastal experience.brHouse Rules & Helpful Infobrbr-Fireplace: For decorative purposes only, please do not use.brbr-Trash & Recycling: Please remove all trash, including any food left in the fridge, and place bagged trash in the outdoor bins.brbr-Recycling does not need to be sorted, except for bottles and cans that are refundable in Maine. These can be set aside—feel free to return them to a local redemption center, or housekeeping will collect them.brbr-No Smoking: Smoking is not permitted anywhere inside or outside on the property.brbr-No Fireworks: Fireworks are strictly prohibited on the premises.brbr- No Parties are allowed or a $500 additional cleaning fee will apply.brbr-Damage Policy: Accidents happen—please report any damage promptly so we can address it quickly. The Damage Waiver covers unintentional damage to the property and its contents up to $1500, provided damages are reported to Ohana Vacations before check-out. (Airbnb reservations excluded.)brbr-Starter Pack: Ohana provides a starter supply of essentials (toilet paper, paper towels, soap, etc.). Guests are responsible for replenishing the following items as needed.brbrThese items ARE NOT included...brbr-Mosquito/tick repellentbrbr-Personal hygiene itemsbrbr-Sunscreenbrbr-Beach towelsbrbrGrill Use: If a grill is available, please do not move it and keep it 5–10 feet from the house at all times. Kindly clean the grill after each use.brbrIf propane runs out, please contact Ohana customer service for a replacement.brbrPrivate Wells & Septic Systems: Some of our homes use private wells and septic systems. brbr-Please: Flush only toilet paper—no wipes, feminine products, or other items.brbr-Avoid driving on the lawn, as pipes run underground.brbr-Be mindful of water usage.

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Bath

Sleeps

$362.07

/ Nightly

Private Vacation Home

Boothbay Harbor from a Unique Perspective: Stay on the Sailboat Windsong at a Full-Service Marina!

Boothbay Harbor, Maine, United States

Windsong: A Unique Harborside Experience on a 42-Foot KetchbrbrCottage Connection is proud to offer what may be the most unique vacation rental experience in our 33-year history. We invite you to experience the beauty and wonder of life on the water in Boothbay Harbor by staying aboard Windsong, a 42-foot ketch sailboat. Best of all, no boating experience is required—this vessel is securely docked at a vibrant marina, staying right heah so you can enjoy the nautical lifestyle with all the comforts of a seaside cottage.brbrCharming FeaturesbrStationary Harborside Living: Enjoy a front-row seat to the harbor’s activity from the comfort of your boat. Windsong is securely moored at Carousel Marina, offering a close-up view of the water and the surrounding fleet.brMarina Amenities: Your stay includes access to the marina's facilities, including a restaurant and bar, laundry, and showers. For a fun local experience, you can even hop on the water taxi!brComfort on the Water: Relax in air-conditioned comfort surrounded by beautiful wooden decks, bulkheads, and ceilings with plenty of headroom.brOutdoor Deck Space: The aft deck features teak chairs and an on-the-rail propane grill, making it the perfect spot for sunset cocktails and dinner with a view.brModern Salon: The interior salon serves as your living and dining area, complete with cushioned seating, a table for dining or puzzles, a Smart TV, and Wi-Fi.brWalk-to-Town: Located at the head of Boothbay Harbor, you are just an easy walk away from the town’s diverse shops, restaurants, and boat excursions.brbrNOTE: To ensure safety and the best possible experience, Windsong is not suitable for children under 12. Please note that while the boat has toilets (heads), the marina's shower house provides the most spacious and comfortable experience.brbrThe Details:brbrMinimum Stay: 3-Night Minimum (June - September).brbrBEDROOMS: (1) Queen Bed (Aft Cabin), (3) Twin Berths (Forward areas). Sleeps up to 5.brbrBATHROOMS: (1) Half Bath/Water Closet on board. Showers are located at the Marina.brbrDOGS PERMITTED No, pets are not allowed.brbrLINENS & TOWELS INCLUDED Yes, linens and towels are included in your reservation.brbrExplore the RegionbrHarbor Adventures: With the harbor at your fingertips, you can easily rent a kayak or board a local schooner for a sunset cruise or whale-watching trip.brCarousel Marina: Take advantage of the on-site restaurant and bar for a convenient and delicious meal without leaving the docks.brDowntown Boothbay Harbor: Walk into town to explore the historic footbridge, local art galleries, and the bustling waterfront shops.brParking: Parking is provided for one vehicle at the marina; additional parking is available at the Cottage Connection office.brbrBook your unique harborside escape on Windsong today!brbrCOTTAGE CONNECTION Vacation Rentals. Privately Owned. Professionally Managed. Trusted since 1993. Cottage Connection was one of the first vacation rental companies in the Midcoast region of Maine. Since being founded by Jeff and Audrey Miller in 1993, Cottage Connection has been trusted by homeowners and vacationers alike to connect each family with the perfect vacation cottage.

3

Bed

1

Bath

5

Sleeps

$668

/ Nightly

Private Vacation Home

Downtown Waterfront Cottage with shoreline sitting room

Boothbay Harbor, Maine, United States

Welcome to this rustic-chic coastal cottage, a tastefully appointed waterfront retreat located just a short walk to the heart of downtown Boothbay Harbor. This newly renovated 3-bedroom, 2-bath split-level home offers the perfect blend of peaceful coastal living and walk-to-everything convenience, with lovely water views and the gentle rhythm of harbor life just outside your door.brbrThe open-concept main living area features light and airy interior, natural textures, and designer-selected furnishings that create a warm, comfortable atmosphere. The living room captures sweeping harbor views and includes plush seating, a 32” Samsung TV with cable, and easy access to the porch for enjoying ocean breezes and passing boats.brbrThe bright eat-in kitchen offers open shelving, white appliances, and two dining areas—a breakfast nook for four and a farmhouse table for six. Upstairs, three serene bedrooms each feature a queen bed, comfortably accommodating up to six guests. A full bath with walk-in shower is located upstairs, with a second full bath on the main level.brbrOutdoor living shines with a waterfront pavilion ideal for dining, morning coffee, or sunset cocktails overlooking Mill Cove. Additional amenities include Wi-Fi, washer and dryer, baseboard heat, air conditioning in the bedrooms, and parking for two vehicles.brbrJust steps from downtown shops, restaurants, and waterfront activities, guests can enjoy whale watching, sailing excursions, scenic trails, and the Coastal Maine Botanical Gardens nearby.brbrThings to know: No pets. Parking for two vehicles. Renters must be 21 or olderbrHouse Rules & Helpful Infobrbr- Parking: This house shares a driveway with the adjoining property. It is essential that the driveway is not blocked. Please park at the end of the driveway up to the garage or angled into the back yard so that the adjacent property owner will have vehicular access to his back yard. You may also park in front of the house along the street. brbr-Trash & Recycling: Please remove all trash, including any food left in the fridge, and place bagged trash in the outdoor bins.brbr-Recycling does not need to be sorted, except for bottles and cans that are refundable in Maine. These can be set aside—feel free to return them to a local redemption center, or housekeeping will collect them.brbr-No Smoking: Smoking is not permitted anywhere inside or outside on the property.brbr-No Fireworks: Fireworks are strictly prohibited on the premises.brbr- No Pets or Parties are allowed or a $500 additional cleaning fee will apply.brbr-Damage Policy: Accidents happen—please report any damage promptly so we can address it quickly. The Damage Waiver covers unintentional damage to the property and its contents up to $1500, provided damages are reported to Ohana Vacations before check-out. (Airbnb reservations excluded.)brbr-Starter Pack: Ohana provides a starter supply of essentials (toilet paper, paper towels, soap, etc.). Guests are responsible for replenishing the following items as needed.brbrThese items ARE NOT included...brbr-Spices & condimentsbrbr-Mosquito/tick repellentbrbr-Personal hygiene itemsbrbr-Sunscreenbrbr-Beach towelsbrbrGrill Use: If a grill is available, please do not move it and keep it 5–10 feet from the house at all times. Kindly clean the grill after each use.brbrIf propane runs out, please contact Ohana customer service for a replacement.brbrPrivate Wells & Septic Systems: Some of our homes use private wells and septic systems. brbr-Please: Flush only toilet paper—no wipes, feminine products, or other items.brbr-Avoid driving on the lawn, as pipes run underground.brbr-Be mindful of water usage.

3

Bed

2

Bath

6

Sleeps

$393.49

/ Nightly

Bed & Breakfast

Boothbay Harbor King Suite - Room 5 at Greenleaf Inn - Harbor Views!

Boothbay Harbor, Maine, United States

Ocean View King Room – Greenleaf Inn Room 5, Boothbay Harbor, MainebrbrWelcome to Greenleaf Inn Room 5, a spacious and sunlit second-floor retreat in the main house, offering breathtaking views of the open Atlantic Ocean. Perfect for couples or solo travelers, this room combines comfort, style, and convenience in the heart of Boothbay Harbor.brbrEnjoy a restful night on a luxurious king-size Helix mattress, complemented by matching nightstands and smart lamps with built-in charging ports. A cozy reading chair provides a relaxing spot to unwind after a day of coastal exploration.brbrFor your comfort, the room includes a ceiling fan, as well as localized air conditioning and heating, making it ideal for all seasons.brbrThe private en-suite bathroom is extra spacious and comes stocked with two sets of towels and two plush robes, adding a touch of luxury to your stay.brbrLocated just minutes from downtown Boothbay Harbor's shops, restaurants, and harbor tours, Room 5 offers the perfect blend of New England charm and oceanfront serenity.

1

Bed

1

Bath

2

Sleeps

$393.49

/ Nightly

Bed & Breakfast

Boothbay Harbor King Suite - Room 4 at Greenleaf Inn - Fireplace, Harbor Views!

Boothbay Harbor, Maine, United States

King Room with Harbor and Island Views – Greenleaf Inn, Boothbay Harbor, MainebrbrEnjoy a peaceful coastal retreat in this spacious second-floor King room at the Greenleaf Inn, ideally located in the heart of Boothbay Harbor, Maine. This bright and inviting room offers stunning dual water views—one overlooking the tranquil inner harbor, the other stretching out toward scenic islands and iconic lighthouses.brbrThe room features a plush pillow-top king-sized bed, dual nightstands, a comfortable sitting area, and a full closet. Climate control is personalized with a ceiling fan and individual air conditioning and heat, ensuring comfort year-round.brbrThe private en-suite bathroom includes a large walk-in shower, soft towels, and plush robes, providing a spa-like experience after a day of exploring the Maine coast.brbrJust minutes from Boothbay Harbor’s shops, restaurants, boat tours, and coastal trails, this room is ideal for couples or solo travelers looking for comfort, views, and classic New England charm.

1

Bed

1

Bath

2

Sleeps

$422.41

/ Nightly

Private Vacation Home

Hillside Respite by Sea Maine

Boothbay Harbor, Maine, United States

***NEW LISTING PHOTOS COMING SOON***brbrWelcome to a comfortable coastal home in Boothbay Harbor! Perfect for families or small groups. With three bedrooms, flexible sleeping arrangements, and a peaceful setting just minutes from downtown, this home offers a convenient and relaxing base for exploring Maine’s coast. This home is located down the road from Barrett`s Park where Sea Maine manages another home, Cottage at Lobster Cove, perfect for large families traveling to the region together!brbrIMPORTANT:brInstead of placing a security deposit hold on your card, we include a small, non-refundable $25 damage waiver in the reservation total—so your funds remain available throughout your trip. This Waiver covers damages up to $300.br• Quiet hours are 9:00 PM – 9:00 AM. Please respect our neighbors at all times.br• Maximum occupancy is as shown on the listing. Additional guests are subject to $25/person/night and may result in cancellation if excessive.br• A mandatory, non-refundable damage waiver is included in your reservation total in place of a security deposit. Guests remain responsible for damage exceeding coverage or resulting from negligence or rule violations.br• Pets are not allowed without prior approal and non-refundable pet rent.br• No smoking or vaping anywhere on the property (indoors or outdoors).br• Open flames (fireplaces, fire pits, etc.) require prior written approval.br• No parties, events, or large gatherings without written approval.br• Waterfront/dock use (if applicable) is at your own risk and may require an additional waiver.

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$395.63

/ Nightly

Cottage

Come and enjoy our Boothbay Cottage

Boothbay Harbor, Maine, United States

The Boothbay Harbor Region is considered one of the perfect Maine destinations. Rich in history, awash in local color and home to a thriving Maine community, there is something for everyone to be found.brbrCome stay in this cozy guest cottage with a spectacular view and explore Maine's coast. Fully furnished, this house will be your home away from home right on the water. Beautiful lighthouses, fine restaurants, world-class golfing, dozens of natural trails and other adventures are easily within reach. Take part in events such as the Windjammer Days in June or just relax outside on a sunny July day.brasbrBoothbay Harbor offers a wealth of activities for all ages. Some of them include: boating, cruises, sailing, kayaking, whale watching, tours, scenic train rides, lighthouses, museums, exhibits, galleries, an aquarium, festivals, golfing, mini-golfing, bowling, walking / hiking trails, shopping, antiques, fine dining, fresh seafood and lobster.brbrThe Ultimate Spot for Your Perfect Maine Vacation!brbrSmall beach perfect for swimming and fishingbrFully furnished, two bedrooms: one queen, two twinbrHardwood flooringbrDeck with gas grillbrFull kitchen with new appliancesbrWasher and DryerbrA step away from the Spruce Point Inn Resort & SpabrWatch the windjammers and lobster boats go by with a clear view of the ocean.brPlease note that the dock shown in the photos is no longer present due to the winter storms of 2023/2024.

2

Bed

1

Bath

4

Sleeps

$497.02

/ Nightly

Private Vacation Home

You and Your Dog Will Love This Boothbay Harbor Cottage

Boothbay Harbor, Maine, United States

Bay Street Cottage: Harbor Charm with A/C & Fenced YardbrbrDiscover your quiet retreat just steps from the action at Bay Street Cottage, an adorable and fully renovated home tucked onto a peaceful side street in the heart of Boothbay Harbor. The owners specifically chose this spot for its rare combination of tranquility and town accessibility. This charming two-bedroom cottage provides a serene atmosphere with a lush, private feel, while remaining just an easy stroll away from the vibrant energy of the harbor.brbrCharming FeaturesbrFull Air Conditioning: Escape the summer heat! This is one of the rare homes in the area that is fully air-conditioned, ensuring a cool and comfortable sanctuary throughout your stay.brFenced Yard & Pet Ready: A beautiful, fully fenced-in yard is a highly sought-after feature in the harbor. It’s the perfect safe space for your furry companions to enjoy the Maine air.brLush Outdoor Living: Relax on the spacious deck surrounded by lovely plantings that create a private and welcoming garden atmosphere.brEasy Single-Level Living: Designed for convenience, the main living area, the full bathroom, and one of the king bedrooms are located on the first floor.brModern Comforts: Featuring two King beds, this home is ideal for couples or small families looking for a high-end sleep experience.brQuiet Side-Street Location: Enjoy the best of both worlds—peaceful nights away from the crowds, with the harbor’s best attractions just minutes away.brbrBringing a furry friend The fenced yard is a true gem in Boothbay Harbor, allowing your family dog a safe place to run and play while you relax on the deck.brbrThe Details:brbrMinimum Stay: 4-Night Minimum. Stay for a week or longer to receive a better value on your booking!brbrBEDROOMS: (1) King, (1) KingbrbrBATHROOMS: (1) Full bathroom with shower/tub combo.brbrDOGS PERMITTED Yes! Up to two adult dogs of most breeds are welcome.brbrLINENS & TOWELS INCLUDED Yes, linens and towels are included in your reservation.brbrExplore the RegionbrWalkable Downtown: An easy 8-minute walk brings you to the heart of downtown Boothbay Harbor for shopping, diverse dining, and waterfront activities.brFisherman’s Memorial: Walk over to this popular local landmark for some of the most iconic views of the harbor and the working waterfront.brCoastal Maine Botanical Gardens: A short drive away, explore acres of world-class gardens and woodland trails.brBarrett Park: Head over to this nearby seaside park for a picnic, a quick swim, or to let the dogs enjoy the shoreline.brbrBook your fully air-conditioned Boothbay Harbor retreat at Bay Street Cottage today!brbrCOTTAGE CONNECTION Vacation Rentals. Privately Owned. Professionally Managed. Trusted since 1993. Cottage Connection was one of the first vacation rental companies in the Midcoast region of Maine. Since being founded by Jeff and Audrey Miller in 1993, Cottage Connection has been trusted by homeowners and vacationers alike to connect each family with the perfect vacation cottage.

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Bath

Sleeps

$242.19

/ Nightly

Condo

Waterfront Condo: Walk to Downtown Boothbay Harbor

Boothbay Harbor, Maine, United States

Cove Views | Breakfast Nook | WFH Friendly | Ground-Floor Unit | 4 Mi to Coastal Maine Botanical GardensbrbrA serene coastal retreat awaits at this Boothbay Harbor vacation rental! With a picturesque waterfront setting and a prime location just a short walk from downtown shops and eateries, this 2-bedroom, 2-bath condo is perfect for a seaside stay. Embark on a sailboat tour, visit Coastal Maine Botanical Gardens, or check out Barrett's Park before returning home to relax on the furnished patio.brbr-- THE PROPERTY --brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 queen bedbr- Bedroom 2: 2 twin bedsbr- Additional Sleeping: 1 queen air mattressbrbrINDOOR LIVINGbr- Smart TVs w/ cable, gas fireplacebr- Laptop-friendly desk w/ printerbr- Breakfast nook, dining tablebr- En-suite bathroom, walk-in showersbrbrOUTDOOR LIVINGbr- Furnished patio w/ cove view, electric grillbr- Spacious yardbrbrKITCHENbr- Refrigerator, stove/oven, microwave, dishwasherbr- Drip coffee maker, toasterbr- Dishware & flatware, cooking basics, spicesbrbrGENERALbr- Keyless entry, self check-in, free WiFi, central heatingbr- Washer & dryer, laundry detergent, iron/board, trash bags/paper towelsbr- Towels/linens, complimentary toiletries, shampoo/conditioner, hair dryerbrbrFAQbr- No A/Cbr- 2 exterior security cameras (facing out)brbrACCESSIBILITYbr- Single-story condo, step-free entrybr- 2 interior steps required to access living roombrbrPARKINGbr- Designated parking spots (2 vehicles)br- Overflow lotbrbr-- THE LOCATION --brbr- Walking distance to downtown dining & shopping, boat tours, Hodgdon Marinabr- 3 miles to Maine State Aquariumbr- 4 miles to Coastal Maine Botanical Gardensbr- 2 miles to Barrett's Parkbr- 60 miles to Portland Int’l Jetportbrbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- While this single-story condo offers step-free entry, 2 interior steps are required to access the living roombr- The designated parking spots are not adjacent to the unit. Guests must travel across the parking lot to access the condobr- This property does not offer air conditioningbr- Your safety matters. The property features 2 Ring security cameras located at the front and back doors facing outward. The cameras do not look into any interior spaces. The cameras record video and sound when motion is detected

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Sleeps

$360.2

/ Nightly

Private Vacation Home

Harborview Perch... spacious & open floorplan, privacy, harbor view, amenities

Boothbay Harbor, Maine, United States

Harborview Perch: comfortable & inviting with spectacular, elevated views of Boothbay Harbor! brbrHarborview Perch accommodates 6 adults very comfortably. There is a bright & spacious living room and fully outfitted cook's kitchen. Master bedroom with king-size bed and private powder room located on the first floor. There is an additional full bath also on the first level. Two other queen bedrooms and powder room are located on the second level. (Note that the property is on a somewhat elevated site and has a steep driveway and one flight of stairs up to the entry. This results in a terrific view, but may be difficult for those with limited mobility.)brbrThis newly renovated home offers ac/heat, Wi-Fi, a 72 smart tv and outdoor BBQ. Nicely stocked with games, puzzles and books for rainy days. Parking available for up to 3 vehicles. All of this is just a one-mile scenic walk to downtown shops and restaurants in historic Boothbay Harbor. brbr“Harbor Perch” provides you with privacy, peace & quiet and a perfect home-base for exploring the picturesque Maine coast. Relax and enjoy the views. Watch the lobster boats and recreational boating in the harbor below. Bright and sunny....enjoy the beautiful sunrises; summer evenings are lazy and long.brbrAlthough Harborview Perch is new to VRBO the hosts are not. We recently sold a property in Cundy's Harbor that we rented through VRBO for the past 18 years. We earned the Premier Host badge for this property and are confident that we will earn it here in the future as well. brbrExplanation of fees:br- Linens: The fee covers fresh bath & kitchen towels and bed sheets along with bath mats at the beginning of each stay. For extended stays, linens will be refreshed each Saturday with the fee repeated. For any mid-week laundry, there is a washer & dryer available in the home. br- Cleaning: The house is of course thoroughly cleaned prior to your arrival. Additional cleaning will be provided each Saturday of extended stays with the fee repeated. br- Property Fee: This is an alternate to security deposits and is essentially owner provided insurance to cover any accidental damage up to $1500.brbrFor multi-week stays, linen service and cleaning will be provided between 10am and 3pm on each Saturday.

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Bath

Sleeps

$358.14

/ Nightly

Private Vacation Home

Coastal Cottage - Walk to Everything

Boothbay Harbor, Maine, United States

Freshly renovated coastal cottage for rent. This special property is a 5 min walk to downtown Boothbay Harbor. Don’t fight for a parking space, just stroll down to the restaurants and shops! brbrThe home features a brand new fully-equipped chef’s kitchen, spacious dining room seating 8, living room with a large pull-out sectional and decorative fireplace, front porch, 3 well-appointed bedrooms upstairs with newly renovated bath (high step up into tub). Enjoy the half acre site w/ wild flowers and view of Mill Cove (no water access)

3

Bed

1

Bath

6

Sleeps

$796.23

/ Nightly

Private Vacation Home

NEW 2026! SS Boothbay: Renovated Historic Waterfront Home with Private Dock, AC & Walk to Town

Boothbay Harbor, Maine, United States

SS Boothbay: A Captain’s View of Mill CovebrbrNew for 2026!brbrStep into a piece of maritime history at SS Boothbay, a stunningly renovated historic home overlooking the peaceful waters of Mill Cove. Originally built by master shipbuilders from Bath — the same craftsmen responsible for the majestic schooners like the Courtney C. Houck and Zebedee E. Cliff that have found their final resting place in these very waters—this home is a tribute to Maine’s seafaring legacy. Today, it stands as a light, airy, and nautical retreat, offering the perfect blend of breezy living and classic Maine charm.brbrCharming FeaturesbrHistoric Craftsmanship: Meticulously renovated to preserve its character, you’ll find original exposed beams and handsome slate floors in the entry, now complemented by modern furnishings and high-end fixtures.brOpen-Concept Living: The spacious kitchen, dining, and living areas are designed for connection. The large kitchen features ample counter space and a central island with a breakfast bar—the ultimate hub for morning coffee and evening appetizers.brThe Retreating Room (aka The Chart Room): An upstairs sanctuary overlooking the water offers a flexible space for those who need a quiet desk for remote work, a sunlit spot for puzzles, or a secondary lounge for movie nights.brWater Access: Take advantage of your private dock and float on Mill Cove. Whether you are launching kayaks or simply watching the tide come in, the water is your constant companion. The sunsets are beautiful and ever-changing.brOutdoor Oasis: A huge yard leads down to the water, while a deck on the coveside side provides the perfect stage for sunset dinners and summer BBQs on the gas grill.brModern Comforts: Experience the rare luxury of air conditioning, ensuring you stay cool even on the warmest Midcoast afternoons.brbrWith its crescent-shaped driveway accommodating up to four cars and an easy, level walk into the heart of Boothbay Harbor, SS Boothbay offers the perfect balance of private waterfront living and village convenience.brbrThe Details:brbrMinimum Stay: 4-Night Minimum. Stay for a week or longer to receive a better value on your booking!brbrBEDROOMS: 4 Bedrooms: (1) Queen Downstairs, (1) King, (1) Queen, (2) Twins.brbrBATHROOMS: 3 Full Bathrooms. DOGS PERMITTED Yes! Up to two adult dogs of most breeds are welcome.brbrLINENS & TOWELS INCLUDED Yes, linens and towels are included in your reservation.brbrExplore the Harbor & BeyondbrWalk to Town: Enjoy an easy stroll into downtown Boothbay Harbor for world-class dining, local boutiques, and the famous footbridge.brCoastal Maine Botanical Gardens: Just 2.5 miles away, discover the stunning gardens and famous wooden trolls that make this a must-see destination.brMill Cove History: Keep your eyes on the water at low tide to spot the bones of the historic schooners scuttled in the cove—a hauntingly beautiful reminder of the region’s shipbuilding past.brBoating Adventures: Use your private dock as a base for exploring the inner harbor or catch one of the many excursion boats from the village wharves.brbrBook your historic stay at SS Boothbay and reconnect with the magic of the coast!brbrCOTTAGE CONNECTION Vacation Rentals. Privately Owned. Professionally Managed. Trusted since 1993. Cottage Connection was one of the first vacation rental companies in the Midcoast region of Maine. Since being founded by Jeff and Audrey Miller in 1993, Cottage Connection has been trusted by homeowners and vacationers alike to connect each family with the perfect vacation cottage.

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Bath

Sleeps

$1788.97

/ Nightly

Private Vacation Home

The Sea Eagle - Luxury 5 BR Waterfront Home in Boothbay Harbor with Dock & Sauna

Boothbay Harbor, Maine, United States

A completely renovated waterfront home in the heart of Boothbay Harbor, The Sea Eagle is steps from the ocean with a private dock and balconies overlooking the sparkling harbor. Drink morning coffee on the porch while listening to church bells and distant fog horns. Walk to art galleries, shops, restaurants, Mama Di’s bakery and the iconic Footbridge. Swim and kayak from your dock. Adventurous guests may sleep in the unique cove-side bungalow perched on the rocks at the top of the tide. Relax in a newly installed 3 person teakwood dry heat or steam sauna.brThe spacebrThis home was in major disrepair when we bought it in 2020. Extensive renovations from the foundation up were required. My wife and our team of talented craftsman curated every detail, adding in old home charm with antique newel posts, period corbels and restored windows. No part of the home went untouched. The waters-edge shack was ramshackle when we bought the house. This too has been fully restored with a main floor and a loft that can accommodate 3 or 4 adventurous guests who want to sleep inches from the water. Check out our Insta postings at SugarHollowProperties to see before and after pictures.brGuest accessbrThe whole home is available to you. This includes a garage for one car with room for additional cars bedside the house or on the nearby side street.brOther things to notebrOur home has a tidal dock out back. Great for using the kayaks provided, swimming, or just enjoying a glass of wine in the Adirondack chairs while the tide rolls in. There is a first floor full bath with a pull out sofa in a den nearby, making one floor access an option for disabled guests. Please note, the house is very close to a busy street out front and has no fence at the shoreline. These may be a safety issues for toddlers or small children.

6

Bed

4

Bath

14

Sleeps

$413.11

/ Nightly

Private Vacation Home

Newly renovated 3 bedroom, 2 bath bungalow, just steps to downtown BBH.

Boothbay Harbor, Maine, United States

Welcome to School Street! This charming three-bedroom, two-bath bungalow offers everything you need for a comfortable and memorable stay in Boothbay Harbor, Maine. Each bedroom features a queen-size bed and a spacious closet, providing plenty of comfort and privacy. Unwind on the spacious deck with plenty of seating, ideal for morning coffee, casual gatherings, or outdoor dining. Even better, downtown is just minutes away, offering an easy walk to the sights, sounds, and coastal charm of this one-of-a-kind seaside town.

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Bath

Sleeps

$292.14

/ Nightly

Apartment

Pet Friendly-Steps from All-Harbor View Apt Heart of Boothbay Harbor's Downtown.

Boothbay Harbor, Maine, United States

The Starfish is located downtown in the heart of beautiful Boothbay Harbor. brbrThis charming rental has one Queen size bed, and a queen sized futon in living room. Additionally it has Internet, DirecTV, and a fully stocked kitchen and front loader washer/dryer. This apartment has been completely renovated in 2016 and is bright and very comfortable. NON-SMOKING UNIT & BUILDING. brbrThe location is right in the heart of the Harbor just steps away from shopping, restaurants and the waterfront activities. It is on the second floor and has views of the harbor from the bedroom & full views of the quant golden triangle which is exquisitely lit up in the evening and in the heart ❤️ of town. brbrOur very quant beautiful harbor offers many activities including kayaking, paddle boarding, whale watching excursions, daily harbor tours, daily sunset tour, trolley rides, the Coastal Maine Botanical Gardens, and The Gardens A Glow (seasonally) many preserves for hiking, LOTS of Antiquing and many fantastic restaurants and shopping, most just step out the door!!brbrWe also can be found in the Boothbay Harbor Mart & Country Store!brbrBoothbay Harbor Mart & Country Store is centrally located if you need a great cup of organic fresh brewed coffee, a breakfast or lunch snack, a cold Beer or a bottle of Wine, Spirits even a cooler to hold it all in. For those who forget or just like to pack light, we also have toothbrushes, sunscreen, dramamine, and many toiletries/remedies and necessities.brbrIf the calendar is full ask about our Harborview rental, also a larger one bedroom with views. #3509429brbror #3673276 our Three bedrm “Oceanside” in the same location with views.brbrbrWindjammer Day Boothbay Harbor brParade of SailsbrAntique Boat ParadebrBlessing of the FleetbrStreet ParadebrPiratesbrTug of War (over the harbor)brFireworks over the HarborbrLighted Boat ParadebrbrbrCheck out the fun during Fall and Winter too...brbrThe Boothbay Festival of Lights brbrA celebration of signature Holiday events in Maine midcoast’s quintessential seaside towns of Boothbay and Boothbay Harbor! The towns sparkle with thousands of lights and the shops, restaurants and hotels are all open and ready to help you make wonderful Holiday memories!brCheck out the Boothbay Festival of Lights signature events as well as all of the other exciting events and happenings around town – and plan your trip today!br@BoothbayLightsbrwww.BoothbayLights.combrGardens Aglow | The North Pole Express | Festival of Trees | Harbor Lights Festival | The Dough Ball & Gingerbread Spectacular | Holiday Sparkle Fireworksbr#GardensAGlowbrbrhttps://youtu.be/kum3sTW_1UIbr

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Sleeps

$358.61

/ Nightly

Private Vacation Home

Cozy 3 bedroom house with large covered porch just steps from downtown BBH.

Boothbay Harbor, Maine, United States

Welcome to Montgomery Road! This charming three-bedroom home has everything you need for a memorable stay in Boothbay Harbor, Maine. Featuring three comfortable queen beds, the house offers plenty of space and privacy for families or friends traveling together. Start your mornings with coffee or unwind in the evenings on the spacious covered deck, complete with ample seating for relaxing, chatting, enjoying appetizers, or sharing meals together. Best of all, downtown is just minutes away, offering an easy walk to shops, restaurants, and the waterfront charm of this lovely coastal town.

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$389.75

/ Nightly

Private Vacation Home

Boothbay Birch Cottage, near Botanical Gardens

Boothbay Harbor, Maine, United States

Sunny Cape Retreat Near Boothbay Harbor & Coastal Botanical GardensbrbrThis charming, sun-drenched 3-bedroom, 2-bathroom Cape offers the ideal mix of comfort, convenience, and coastal charm for your next vacation.brbrStep inside to discover warm wooden floors in every room. The home's thoughtful layout features all three bedrooms on the second floor—complete with one queen bed, two twin beds, and a king bed fitted with a premium natural latex mattress topper and wall-mounted ductless air-conditioning units to keep you cool on summer days. Upstairs there's also a full bathroom with a tub/shower that's perfect for families with young children. brbrThe main floor features rustic knotty pine ceilings throughout. You'll find a bright and airy dining room with floor-to-ceiling windows, a cozy seating area with a TV for family movie nights, a full bathroom, and a second living area with reading nooks and a dedicated workspace for those who need to log in while away.brbrStep outside onto the spacious wraparound deck to enjoy outdoor dining, relax in the fresh coastal air, or fire up the gas grill for a BBQ cookout. The large backyard is great for kids to play or for a game of cornhole after a day exploring.brbrBirch Cottage's location is ideal for exploring everything the peninsula has to offer. Just down the street is picturesque Boothbay Harbor where you can enjoy the region's best local seafood, craft breweries, ice cream, shopping, and seasonal festivities like the Windjammer Days Festival and July 4th fireworks and parade. Head down to the waterfront piers to rent kayaks, book a whale watch or puffin tour, or grab the ferry to Monhegan Island.brbrThe property is minutes from some of the area's most popular attractions including the renowned Coastal Maine Botanical Gardens, Boothbay Opera House, Carousel Theater, Railway Village Museum, and the Boothbay Farmers Market.brbrThe peninsula is home to the Boothbay Region Land Trust's stunning nature preserves and more than 30 miles of well-maintained hiking trails. Cool off on the nearby beaches at Barrett's Park and Hendrick's Head, or the rugged shoreline at Ocean Point. All are a quick drive or bike ride from Birch Cottage.brbrWhether you're craving lobster rolls, nature walks, or time near the water, this cozy cottage is a comfortable and convenient home base. Just under an hour from Portland, it's the perfect family-friendly escape in Midcoast Maine.brbrPlease note the owners have cats that occasionally visit the home but the home is thoroughly cleaned after.

3

Bed

2

Bath

6

Sleeps

$410.93

/ Nightly

Bed & Breakfast

Boothbay Harbor King Suite - Room 3 at Greenleaf Inn - Balcony, Harbor Views!

Boothbay Harbor, Maine, United States

Green Leaf Room 3 – Spacious King Room with Private Balcony and Stunning Harbor Views | Greenleaf Inn, Boothbay HarborbrbrEscape to coastal elegance in Room 3 at the Greenleaf Inn—your perfect Boothbay Harbor retreat. Located on the second floor, this spacious king bedroom features a private balcony overlooking the picturesque inner harbor. Wake up to breathtaking water views and enjoy your morning coffee while watching the boats drift by.brInside, the room offers a plush king-sized pillow-top bed with nightstands on both sides, a large dresser, and a full closet for your comfort and convenience. The generously sized private bathroom is a true standout, featuring a hand-painted ocean mural that adds a unique and artistic touch to your stay.brWhether you’re planning a romantic getaway or a relaxing solo escape, Room 3 offers a peaceful haven with exceptional views, comfort, and coastal charm—just steps from the heart of downtown Boothbay Harbor.

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Sleeps

$218.0

/ Nightly

Cottage

The Puffin's Nest: Cozy 1-Bedroom Cottage in BBH

Boothbay Harbor, Maine, United States

Relax and unwind in the Puffin's Nest cottage, a 1-bedroom Boothbay Harbor retreat. This beautiful cottage features a queen bed and kitchenette for your convenience. The kitchenette includes a mini fridge. Perfect for a couple's getaway. The Puffin's Nest is also convenient for a couple with a baby or toddler, as the bedroom can fit a pack-n-play next to the queen bed.brbrThe Puffin's Nest cottage has a small, covered porch with a swing. Enjoy your morning coffee al fresco while savoring Maine's gorgeous summer breezes. One parking space is included.brbrThere are sidewalks all the way to town, or if you prefer to ride, the free local trolley stops just across the street in the Brown's Wharf parking lot.brbr**New in 2025: The Puffin's Nest cottage may be rented separately from the Seaglass House, or they may be rented together for larger parties. The two homes share the same yard and driveway but are separate buildings.

1

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1

Bath

3

Sleeps

Vacation Rentals By Owner In Boothbay Harbor, ME

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$1788.97

$413.11

$292.14

$358.61

$389.75

$410.93

$218.0

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