This 1800s schoolhouse is full of charm! Gleaming wide pine floors and beamed ceilings add to the appeal. The home's location is truly what makes it exceptional. Walk 1 minute to the harbor or to our favorite breakfast spot. A 4 minute walk takes you to all Boothbay Harbor has to offer--shops,...

The tiny house cottage is very well appointed using a nautical theme. There is a half bath in the cottage. Then a few steps away is the enclosed kitchen and shower. Parking is very convenient and the shore, dock and kayaks are within site of the tiny cottage. Walking to the town center,...

Our log cabin is nestled in the Sprucewold Community, about a 5 minute walk to a beautiful beach and a 10 minute walk to downtown Boothbay Harbor. It is a spacious 2 bedroom and a loft space with seating area and a bed. Brand new HVAC system and a gas hot water heater were installed in June 2018,...

A Cozy New England Boothbay Harbor, Maine Retreat, with water part views and 5 minute walk to town. These Delightful 1 Bedroom Condo is comprised of a Comfortable Living room, comfy large sofa, swivel armchairs, electric fireplace with flat screen TV. Dining Room has table with 4 chairs, fully...

If you are looking for a picture perfect Maine getaway for a large number of people, you have found the place. At the head of Linekin Bay sits the little village of Bayville. Founded in 1911, the mostly summer community is a step back in time with its own post office, community dock, tidal beach,...

Classic updated saltwater farmhouse on Southport Island, with 1.4 acres of private lovely grounds, gardens, stone walls, and a child's playhouse, all surrounded by trees. Waterfront on Decker Cove. Private dock with a double kayak provided. Large back deck with gas grill, dining table and chairs,...

Newly listed! Hawk's Nest is a beautiful in town studio apartment with a gourmet kitchen and views of Mill Cove. A separate entrance allows for privacy. This bright and airy studio located on the second floor offers an American Leather sleeper sofa designed without bars or springs and is notably...

PROPERTY OVERVIEW Set on the idyllic shores of Boothbay Harbor, this brand-new, all-suite 2BR condo promises a quintessential Coastal Maine getaway. Perched above Maine’s prettiest harbor, this third-floor penthouse offers a unique bird’s-eye view of the water, ships, lobster boats, and village....

Portside is a year-round luxury condo with the charm of a cottage in the heart of historic Boothbay Harbor, Maine. The cottage is in the town center and yet you will find tranquility and privacy inside. We share a dock and float with the other two Back Bay Cottage units and have our own deck on the...

Retreat into the romance of coastal Maine: this exquisite 1800s Boothbay Harbor cottage (1BR, 1BA, sleeps 4) bursts with vintage character and antique charm. Right next door is Mama D’s where you can enjoy a home cooked brunch or lunch. Other activities include sailing the Eastwind or whale...

This charming and immaculate 4BR/2.5BA Cape home has been redesigned with an addition to make it the perfect family spot for groups of six. Sleeping accommodations include a luxurious master suite on the first floor and three bedrooms on the second floor. Sail aboard the Schooner Eastwind, fish...

Stay at this classic and newly refinished 2BR log cabin with exclusive access to Crooked Pine Float. Walk to Boothbay Harbor to explore beautiful Barrett's Park and dine at the infamous Lobster Wharf and the new Oceanside Restaurant and Dock. Sleeps 4. ABOUT THE CABIN Your secluded vintage...

Enjoy a relaxing getaway overlooking the water at this cozy bungalow close to town. You'll be within walking distance to local restaurants and more along Commercial Street, plus you'll have all the comforts of home with a large deck and a gas grill for outdoor entertaining. Located in Boothbay...

It's all about the views at this rustic three-bedroom summer cottage. Gaze across the scenic waters of Lewis Cove and Linekin Bay and out to the open ocean, and enjoy this tranquil retreat with an incredible waterfront location, 280 feet of private shorefront, its own beautiful tidal beach, and...

Savor gorgeous views of Boothbay Harbor from your 1BR/1.5BA waterside retreat. Custom woodwork and a charming post-and-beam structure give this home its unique character. You’ll feel like a true local as you spend mornings sipping coffee down by the dock and watching lobstermen hauling traps....

THIS PROPERTY RENTS SATURDAY-SATURDAY, JUNE -SEPTEMBER. 7-NIGHT MINIMUM REQUIRED.Off-Season Arrival and Departure dates may be flexible. The owners of BAY STREET COTTAGE wanted a quiet get-a-way spot that would still be close to local activities. They found it in this adorable two-bedroom, one-bath...

Tucked among the pines with views towards the ocean, this chic 1BR cabin (sleeps 2) in Boothbay Harbor is newly renovated and includes access to the Sprucewold Beach. Relax on your woodland surrounded deck or take a walk to Boothbay Harbor. INSIDE THE CABIN After parking directly in front of the...

Newly listed! Located at the entrance to downtown Boothbay Harbor, this house has been completely updated. Featuring beautiful hardwood floors and attractive decor throughout, The Red House is a perfect place from which to explore the harbor. An old fashioned front porch welcomes you while the...

Introducing 'Admiral Quarters'- Located in the heart of downtown Boothbay Harbor, this sunlit top-floor 2BR/2BA penthouse (sleeps 6) is walking distance to everything, including restaurants, nightlife, and whale watching tours. INSIDE THE HOUSE Step through the entry door off Commercial Street...

The perfect retreat for couples—and full of New England charm—this crow’s nest hideaway has just enough room for 2, plus a private, romantic deck with lush treetop vistas in summer and ocean views in winter. Easily walk to downtown Boothbay from here. ABOUT THE APARTMENT A private deck...

Historic Cape Cod with Harbor View, Featured in Coastal Living Magazine! Known as 'Fleur de Lis', this traditional Cape Cod home is perfect for antique lovers, history buffs, bookworms, or anyone seeking a traditional Down East experience. Featured in Coastal Living magazine, the house boasts views...

Situated in the heart downtown of Boothbay Harbor, our 1-bed studio harborfront apartment - The Coal Shack - is walking distance to independent shops, restaurants and boat cruise tours. Stroll outside your front door to Pier 1 and Pier 8 to book whale watching tours, or arrange day trips to the...

Named Lobstermen’s Cottage in honor of the original inhabitants, this 3BR/2BA home sits off the road in tranquil East Boothbay Harbor and features a large back deck with a BBQ. Beautiful hardwood floors, an open-concept main living area, and a welcoming seaside décor give this cottage a charming...

PROPERTY OVERVIEW Gordon’s Waterfront Retreat is an expansive 4BR/4BA lakefront getaway. This romantic and spacious haven is perfect for a couple seeking extra room, three couples traveling together, or a family of up to eight. Perched on a freshwater lake, this rental offers a prime location for...

Planning a vacation with another family or for your own small family reunion? If so, this beautiful New England home is for you. Enjoy the outdoor firepit and immediate beach access with this lovely property that offers two separate homes for one price. Located on the Cape Newagen peninsula and...

SALTAIRE Relax and feel renewed energy while smelling the 'salt air' and enjoying a bird's eye view of Linekin Bay. With that new energy, head down the stairs to your dock and float to dangle your feet in the water, swim, drop a line to catch tinker mackerel or wave to a passing seal as he pops his...

Our Maine Home is located on a beautiful stretch of Maine's mid-coast area. Conveniently located in Boothbay minutes from Boothbay Horbor , the house is set in a very private area,on a dirt waterfront road. The custom built Post and Beam home is an ideal vacation home for a family or a couple...

This custom-furnished downtown 3BR/2BA house enjoys proximity to shops, restaurants, and area attractions. Sit on the water’s edge enjoying the comings and goings of waves and wildlife at Mill Cove, a tranquil tidal harbor. Sleeps 6. ABOUT THE HOUSE Immerse yourself in the delights of Boothbay...

Townhouse condominium in a fantastic location, a beautiful relaxing and very spacious home for you to enjoy. Year-round accommodation with easy door-front parking. Waterside location, with an easy stroll to the town wharfs, restaurants and stores. Local amenities galore to make this your...

LA CABINITA, or 'Little Cabin,' is nestled among the spruces, pines and hardwood trees in a picturesque setting that is often the image evoked when dreaming of a Maine vacation. The open floor plan living/dining/kitchen allows for everyone to participate in the conversation, or sit and enjoy the...

Get the authentic New England experience at this bright 1BR, 1BA Captains Quarters apartment (sleeps 4) in downtown Boothbay Harbor near shopping and bars. Enjoy steamed clams, whale-watching boat trips, & Monhegan Island, a nature lover’s paradise! INSIDE THE RENTAL Located above Janson’s...

Newly Listed! This charming one floor cottage sits on McKown Point in Boothbay Harbor. Located only 2 1/2 miles from the center of town, the Caboose Cottage is a perfect vacation spot. The living/dining room has a cathedral ceiling, fireplace and french doors. Enjoy the large gated deck on three...

This immaculate 3BR/1BA log cabin is located in the famed Sprucewold community. Near Boothbay Harbor restaurants and shops, and a short drive from Maine Botanical Gardens. Private beach deeded access, game room, deck. Sleeps 5. ABOUT THE HOUSE This split-level cabin-style cottage is exceptionally...

Plan your escape to this Boothbay Harbor home! With sweeping views and a unique charm throughout, this is a wonderful spot for a family getaway. Less than a quarter of a mile to Railway Point and one mile to the heart of Boothbay Harbor, this home gives you the chance to explore the majestic...

MINIMUM REQUIRED. Off-Season Arrival and Departure dates may be flexible.7-NIGHT THIS PROPERTY RENTS SATURDAY-SATURDAY JUNE - SEPTEMBER. A treasured family home nestled at the end of Grimes Cove is waiting for you to settle in for a Memorable Maine Vacation! This Ocean Point Cottage is ideal for...

At Sunny Woods House everything on one level, The living and dining space, kitchen, dedicated office, media room, bedrooms and 2 full bathrooms all flow from one to the next—no stairs! You will find everything you'd expect to find in a modern year-round house: fully-equipped kitchen (including a...

This charming cottage in downtown Boothbay Harbor is perfect for your next getaway complete with a private hot tub, bay views, easy access to downtown, and parking for two cars. When it's time to get out and explore, take a quick walk to browse unique shops and dine at the town's many eateries....

Located in the Sprucewold community in a quiet, wooded setting just 5 minutes from Boothbay Harbor, this 1BR, 1BA vacation rental (sleeps 2) blends true log cabin charm and modern luxuries, like high-end appliances in the renovated kitchen. Enjoy exclusive beach access to the Sprucewold Colony...

Located in the Sprucewold Community in a quiet, wooded setting just 5 minutes from Boothbay Harbor, this 2BR, 2BA vacation rental (sleeps 4) blends true log cabin charm and modern luxuries like high-end appliances in the renovated kitchen. Enjoy exclusive beach access to the Sprucewold Colony...

PROPERTY OVERVIEW Nestled in a charming New England neighborhood, this adorable 2BR cottage is just a short walk to the bustling downtown area where you can enjoy shopping, dining, and water excursions like sailing on the Schooner Eastwind. Drive 10 minutes and explore the Coastal Maine Botanical...

Whether you're a couple looking for a romantic retreat, a group of three couples, or a family of eight, Gordon's Waterfront Retreat is the perfect 3BR/2.5BA lakeside accommodation. The West Harbor Pond location is ideal for swimming, kayaking and fishing. You’re minutes from Boothbay Harbor's...

SPRUCE POINT ESTATE Wow! This house has it all! The perfect location, right on the ocean, beautiful gardens surrounding the newly renovated estate. Professional kitchen, master bed & en suite bath on the main level along with another bedroom with en suite off the kitchen. Second master suite with...

With ocean views, a wonderful harbor-facing location, and space for five guests and one dog, this three-bedroom Boothbay Harbor home is a perfect escape for families, couples, and vacationers who want to experience one of Maine's most popular coastal towns. Built in 1864, this historic two-level...

Step back in time when you stay at this historic Boothbay Harbor home, a seven-bedroom cottage with a large front porch, a wonderful location, and an abundance of atmospheric Maine charm. Built in 1909, this two-level home sits at the highest point in Boothbay, just a quarter-mile from the two...

THIS PROPERTY RENTS SATURDAYS-SATURDAYS JUNE - SEPTEMBER. 7-NIGHT MINIMUM REQUIRED. Off-Season Arrival & Departure dates may be flexible. A classic seaside family home on the Atlantic Ocean is ready for you to settle in for a memorable Maine Vacation. This four bedroom, three bath cottage is well...

On the quiet East Side, perched on a hill overlooking the harbor this stand alone apartment brings the world of boating in Maine right before your eyes. In addition to enjoying views from inside, you have two decks to enjoy outside. Everything is included in the weekly rental..(sat-sat)...

This newly renovated 2-bedroom log cabin has exclusive access to a private beach club and dock and is minutes to downtown Boothbay Harbor, by car or by foot. Find peace in this secluded, historic location. Vintage meets sophistication in the 2-bedroom, 1-bath cabin with exposed log walls in the...