Holiday rentals with breakfast in Boothbay Harbor

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Top-rated Holiday Accommodation with Breakfast in Boothbay Harbor

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Guest favourite
The serene view showcases a sunrise over the calm waters of the Sasanoa River, reflecting golden hues. Lush greenery frames the scene, while the distant treeline adds depth to the landscape. Soft clouds linger above, enhancing the tranquil atmosphere of the setting.
Cottage in Woolwich
4.91 out of 5 average rating, 204 reviews

Pet Friendly Audubon Bring Your Fishing Gear!

Enjoy the view from this wonderful 1940's waterfront cottage on the Sasanoa River in Woolwich. From here access Reid or Popham Beach State Parks with ease. Visit Maine Maritime museum in Bath, the "City of Ships." Head to Portland for a night out. Just relax and watch the seals, osprey and eagles. Rent a boat to enjoy all this extremely special waterway has to offer. Around the corner is the Kennebec River and Merrymeeting Bay, to the south you'll discover Phippsburg and historical Fort Popham.

Top Guest favourite
A serene vista showcases the city skyline reflected in calm waters, framed by lush green grass and trees. The scene captures a tranquil moment, inviting viewers to appreciate the natural beauty and urban blend surrounding the space.
Home in Back Cove
4.92 out of 5 average rating, 279 reviews

Top Deck - Portland Property with Views!

Views, Views, Views! 2 huge decks overlooking water and city skyline. This home is adjacent to Payson’s Park – Portland’s largest park. 5-7 min ride to downtown Portland and the Old Port’s fabulous bars and restaurants. The main floor has bedroom with bath, kitchen, and living room. The upstairs has a large bedroom with bath, open room that can be used as 2nd living room or a 3rd/4th bedroom space. Sleeps 10 – 12. Off street parking 6-8. Large yard. Portland License #STHR-002587-2020

Top Guest favourite
A private pool area features a colorful inflatable parrot floating in clear water. Surrounding the pool are several lounge chairs arranged for relaxation. Lush trees provide shade, and a fence ensures privacy for the space, which is brightly illuminated by natural sunlight.
Home in North Deering
4.96 out of 5 average rating, 153 reviews

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

Your crew will be close to everything when you stay at this centrally-located place with a pool and spacious yard! Enjoy the home and it is a quick 10 minute uber to downtown Portland to the most popular shops and restaurants. This home is located perfectly to explore greater Portland from beautiful parks/trials to the shopping outlets not far away. This is a family neighborhood and out of respect for my neighbor’s, no loud partying after 10 pm. City of Portland License #: STHR-004465-2022

Guest favourite
A quaint cabin is nestled among lush greenery, featuring a shingled exterior and a red door. Flowering plants adorn the nearby area, and a rustic chair is visible on the grass. Natural light creates a serene atmosphere in this peaceful rural setting.
Guesthouse in Appleton
4.9 out of 5 average rating, 324 reviews

Raven's Crossing - Retreat Cottage

Welcome to Ravens' Crossing , an 1850's farm located in Midcoast Maine in Appleton. With two guest cottages to choose from, you will find yourself in a peaceful, quiet space. Hot tub is working! Breakfast is $40, delivered to your cabin. Shared bath at studio, short walk from cabin; out-house at cabin Whether you choose to receive massage, relax in the sauna, stay in a cottage, you can decide how your retreat desires may be met. Retreat cabin is off-grid. There is a studio apartment for guests

Top Guest favourite
The exterior of a post and beam cottage is shown, featuring a light wood facade and a brown shingled upper section. Two black Adirondack chairs are placed on a wooden deck, accompanied by potted plants. Large windows offer a view of the forested surroundings under a partly cloudy sky.
Cottage in Pownal
4.99 out of 5 average rating, 448 reviews

Dreamy Post&Beam Hideaway Near Portland & Freeport

Escape to a dreamy timber-frame cottage tucked in Maine’s woods! Soaring beams, radiant-heated floors, a king loft bed, and a crackling fire pit await. Sip coffee on one of the two decks, hike Bradbury Mountain (3 minutes away), shop Freeport (10 minutes away), or dine in Portland (20 minutes away)—then return to your cozy hideaway under the stars. Full kitchen, vaulted ceilings, radiant heat floors, private driveway, fire pit and peaceful forest views make it the perfect year-round retreat.

Top Guest favourite
A charming red house is visible from the winding driveway, framed by tall trees and patchy grass. The front porch runs along the house, while two garage doors and a wooden structure are located nearby. A dog can be seen walking along the pathway.
Apartment in Nobleboro
4.92 out of 5 average rating, 210 reviews

Finding Joy

This lovely apartment is above our garage. You can come and go as you please. We have created a place for peace and solitude. Sit on the deck or look out the dining room window and see the woods and wait for the birds and wildlife that may be wonder through the yard. There is coffee and tea available, along with basic breakfast supplies, if you wish. Keyless entry allows for you to come anytime after check-in. Please note, you have to be comfortable with stairs to access the apartment.

Top Guest favourite
A tiny house with a grey exterior sits nestled among lush greenery and colorful flower beds. It features tall windows that allow natural light to flow in, and a bright red door that adds a pop of color. Surrounding steps made of stones lead up to the entrance.
Tiny home in Durham
4.99 out of 5 average rating, 376 reviews

Crow’s Nest Tiny House at Old Crow Ranch

The Crow's Nest Tiny House sits nestled on Old Crow Ranch, a 70-acre working livestock farm, a true example of thriving Maine farmland. You'll be surrounded by fields and pine woods in Durham, Maine. Just outside Freeport and only 30 minutes from Portland, this cozy space makes a calming retreat away from the city - for a night or for a week. Fall asleep listening to the peepers and gazing at the stars, drink your morning coffee while looking out at the cattle grazing in the fields.

Top Guest favourite
The cozy cottage exterior is illuminated in the evening, highlighted by a bright red front door. Soft light glows from the windows, surrounded by lush greenery. A path with wet pavement reflects the light, creating a welcoming entrance amidst the serene wooded surroundings.
Cottage in Boothbay Harbor
4.98 out of 5 average rating, 463 reviews

The Cottage at the McCobb House

Freshly renovated inside and out, the cottage is your private Maine camp. Located on an acre and a half of wooded grounds, and surrounded by forest, the cottage feels secluded, but it’s only a mile to the restaurants, shops, and waterfront attractions of bustling Boothbay Harbor. With hiking trails in the Pine Tree Preserve that adjoins the property and the Lobster Cove Meadow Preserve a five minute walk up the road, you can also explore nature and enjoy the solitude of the woods.

Top Guest favourite
An open-concept living area showcases a kitchen with wooden cabinetry and a central island. Colorful rugs cover the floor, leading to a seating area with a plush couch and vibrant textile accents. Natural light illuminates the space, with a staircase visible in the background.
Guest suite in Brunswick
5 out of 5 average rating, 131 reviews

Glorious Converted 1865 Brunswick Barn in Town!

ANNOUNCEMENT: DURING SPRING SEMESTER (Jan-May) 2026 WE WILL GIVE A DRASTICALLY REDUCED "LOW SEASON" PRICE FOR 1 MONTH OR LONGER STAYS. 5 min walk from Bowdoin campus. Reach out and we're happy to work with you! "Brunswick Beata" is located steps from Bowdoin, restaurants, movies, public transportation & the town green. This colorful, unique and spotless gem is an extraordinarily comfortable and inspired place to stay while in Brunswick & surrounding area! Welcome!

Top Guest favourite
A bright living area features modern furnishings and natural light streaming through two large windows. A cozy seating arrangement includes a minimalist sofa and an accent chair. A wooden media console holds a flat-screen TV, while a round yellow rug adds a lively touch to the space.
Apartment in Hallowell
4.98 out of 5 average rating, 408 reviews

Two Bedroom Mid Century Modern Downtown Apartment

Experience this amazing two bedroom Mid-Century Modern apartment in Downtown Hallowell. This is newly renovated & steps away from a variety of restaurants & pubs. It has all the fun and funky charm of the early 1960’s with bright colors, rich woods, clean lines & shag rugs. All the modern comforts including stainless steel appliances, vessel sinks, soaker tub & new beds. A couple miles from the State Capital and centrally located between Brunswick and Waterville.

Superhost
A spacious living area features wooden accents and a warm-toned ceiling, with a mix of seating options including two black chairs, a tan sofa, and wooden stools. A large wooden coffee table sits atop a light-colored area rug, and a flat-screen TV is mounted on the wall.
Farm stay in Gray
4.84 out of 5 average rating, 346 reviews

The Retreat at Crystal Lake Farm

This getaway features two spacious bedrooms plus an upstairs bedroom loft, sleeping up to 6 with ease. The large bathroom is accessed by both the master bedroom and living room and features on-site laundry. For guests who love to cook the kitchen is fully equipped and the deck is a perfect place to relax in the summer and enjoy the view. In colder seasons guests are encouraged to cozy up by the wood-burning stove or use the outdoor BARREL SAUNA.

Top Guest favourite
A bright entryway features a light-colored door flanked by windows. A simple staircase leads to the second floor, while a small hall opens to the kitchen area. Natural materials are incorporated through woven basket and striped textiles hanging on hooks.
Apartment in Rockland
5 out of 5 average rating, 108 reviews

1 Block to Beach • Walk Downtown • Peaceful Escape

Renovated 1860s Cape Cod in Rockland’s coveted South End, just 1 block from the beach. Enjoy the scenic boardwalk into town to restaurants, galleries, shops, and the seasonal farmers’ market. Bright, uncluttered spaces with modern amenities create a peaceful retreat — perfect for couples, small families, or anyone seeking a quiet coastal getaway.

Popular amenities for Boothbay Harbor Holiday Accommodation with Breakfast

Quick stats about holiday rentals with breakfast included in Boothbay Harbor

  • Total holiday rentals

    Explore 30 holiday rentals in Boothbay Harbor

  • Nightly prices starting at

    Boothbay Harbor holiday rentals start at $171 AUD per night before taxes and fees

  • Verified guest reviews

    Over 610 verified reviews to help you choose

  • Wi-Fi availability

    30 of Boothbay Harbor holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Boothbay Harbor rentals

  • 4.7 Average rating

    Boothbay Harbor stays receive an average rating of 4.7 out of 5 from guests

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