East Side Cove is a retro style ranch home with lots to offer! Get cozy with a book in the sunroom, have lunch at the picnic table on the outdoor deck, enjoy cocktails down on the dock, play games on the lawn, or take a kayak out into the cove. This house has three bedrooms including one bedroom...

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

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...

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...

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...

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...

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...

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,...

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...

Newly listed with Special Autumn Rates! 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...

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...

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...

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 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...

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...

This cottage is located on the east side of Boothbay Harbor walking distance to town by a connecting footbridge. The cottage has a well equipped kitchen, 2 downstairs bathrooms and an upstairs 1/2 bath. Offering a glassed in dining area and deck off the back, a downstairs master bedroom and...

PROPERTY OVERVIEW Set on the idyllic shores of Boothbay Harbor, this brand-new, all-suite 2BR condo promises a quintessential Cape Cod 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. Enjoy...

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...

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...

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...

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...

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....

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...

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 and french doors opening to decks on both front and bak. Enjoy the large gated...

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...

THIS PROPERTY RENTS SATURDAY - SATURDAY, JUNE - SEPTEMBER 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 cottage, with fenced...

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,...

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...

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...

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...

THIS PROPERTY RENTS SATURDAYS-SATURDAYS JUNE - SEPTEMBER. 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 equipped and comfortably...

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...

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)...

Just past the Boothbay Harbor Yacht Club sits this 4 bedroom home featuring a large living room, water view dining room, a sun room, and spacious master suite with private bath. Add to that 3 additional bedrooms, a generous kitchen, large deck, fenced backyard, and you've got the perfect place from...

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...

A cozy little place perfect for 2 but can sleep up to 4. Pine Crest is a spacious one bedroom cabin with cathedral ceilings, brick fireplace, and a skylight in the open living/kitchen area. The entry consists of an enclosed porch and the back porch looks out to the Linekin Heights Association...

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...

LAZY DAYS Great place for kayakers! Lazy Days is the perfect spot to watch the ‘commuters’ (i.e. boat traffic) come and go into Boothbay Harbor and out to the Atlantic. From your private water-side deck, you have one of the best views around. Relax with your beverage of choice and watch the sun go...

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...

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...

Newly Listed and Autumn Rates! If you like a cabin in the woods but love the smell of the sea, you have found the best of both worlds at the Woodland Cabin. Snuggled amidst evergreens is a completely renovated log cabin with a step down master bedroom with queen bed and loft with 2 single beds....

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...

Located 5 minutes from downtown Boothbay Harbor, this classic 5BR/2BA cabin in the pines has a cozy feel and stunning water views. Relax on the upstairs and downstairs decks, or kick back in the airy great room. The two downstairs bedrooms have their own private entrance and bath. Sprucewold is...

A classic 1800's saltwater farmhouse with dock on a tidal cove in Southport, Maine. Beautiful gardens and a private 1.4 acre yard surrounded by trees. Stone walls, a child's playhouse, and adironndack chairs by the water. Bright and cheery updated home with well equipped modern kitchen, antique...

There's room for up to 10 guests at this lovingly restored historic Boothbay Harbor home. Your 3BR/2BA abode is minutes of a walk from downtown, but you're still far enough away from the bustle for peace and quiet. Enjoy water views and a tasteful nautical vibe throughout. The back deck and...