Vacation Rentals By Owner In Bailey Island, ME

Welcome to Parciak Cottage!brbrNestled at the end of Steamboat Road and resting directly on the pebbly shoreline of Casco Bay, Parciak Cottage offers a truly classic Maine coastal escape. Perfectly positioned to capture southwest-facing sunsets, this charming one-bedroom retreat sits just steps from its own private deck, an ideal spot to sip your morning coffee, unwind with an evening glass of wine, or simply watch the lobstermen haul their traps as seals bob and play in the water just offshore.brbrWith all living space on one easy-access level, this cottage is wonderfully suited for guests who prefer to avoid stairs. As you step inside, you're greeted by a cozy living area that seamlessly opens to the updated galley-style kitchen. Large windows allow you to enjoy views of the water from both spaces, whether you're curled up on the loveseat and armchairs, or preparing dinner in the comfort of a full-size gas stove and refrigerator. A small dining table provides seating for two—perfect for a romantic coastal meal.brbrFollow the hallway toward the back of the cottage and you'll find a full bathroom with a stand-up shower before arriving at the serene bedroom. Outfitted with a comfortable queen-size bed and ample closet space, the bedroom also features a window framing a peaceful view of the ocean—allowing you to drift off to sleep with the soft sounds of the bay.brbrOutside, your private deck and shoreline are the heart of Parciak Cottage. Pull up one of the provided chairs, breathe in the salty sea air, and watch the sun melt into the horizon. With its intimate size, unbeatable location, and quiet coastal charm, this cottage offers everything you need for a sweet and simple romantic getaway on Bailey Island.brbrCome experience the magic of Maine's coast...you won't regret it.brbrPlease Note:brThis property rents Saturday–Saturday in summer. The calendar will show available check-in and check-out days, while the week in between will be grayed out.

This sweet cottage offers a shared pebbly beachfront and gorgeous sunset views

Bailey Island, Maine, United States

Bed

Bath

Sleeps

$218.57

Welcome to Hay!brStep back in time and enjoy the charm of coastal Maine at Hay, a rustic yet comfortable three-bedroom cottage with limited views of scenic Mackerel Cove. Perfect for families or small groups seeking a quiet, historic retreat, Hay combines the character of a turn-of-the-century home with modern amenities to make your stay both memorable and convenient.brInside, the cottage maintains its classic Maine charm with wood-paneled walls and period antiques throughout. The main floor features a spacious kitchen with updated appliances, an open concept living and dining area, a half bath, and a laundry room. The living area includes a brick fireplace adding to the cozy atmosphere (please note the fireplace is not available for renter use). From here, enjoy views of Mackerel Cove through the windows or step out onto the covered porch to soak in the sea air. Though please note the porch screens are currently being repaired.brUpstairs, the cottage offers three comfortable bedrooms with a total of four beds:brOne bedroom with a queen-size bedbrOne bedroom with a full-size bedbrOne bedroom with two twin bedsbrThe second floor also includes a full bathroom with shower and tub, providing convenience for everyone in your group.brFor those who need to stay connected, Hay also features a dedicated office space with wireless internet and a printer, so you can keep up with work while still enjoying your coastal retreat.brLocated just a short walk from Little Harbor, a pebbly beach perfect for swimming, and with easy walking paths across the island, Hay provides a fantastic location for exploring Orr's Island and soaking up Maine's coastal beauty.brWhether you're enjoying a morning coffee on the porch, exploring nearby beaches, or simply relaxing inside this charming historic home, Hay offers the perfect balance of rustic character and modern comfort.brPlease Note:brFireplace is not available for renter use.

Historic cottage with right of way to Little Harbor!

Bailey Island, Maine, United States

Bed

Bath

Sleeps

$123.4

Welcome to Sand Dollar!brbrSearching for the perfect coastal couples' escape You've found it! Sand Dollar is the charming middle cottage in a trio of beloved sister properties, offering a cozy retreat with shared amenities and some of the most enchanting ocean views on the island. Whether you're seeking serenity, sunsets, or seaside adventures, this recently updated one-bedroom cottage has everything you need for a memorable getaway.brbrThough compact in size, Sand Dollar is thoughtfully designed. The main level features a full kitchen, a dining area, and a full bathroom with a stand-up shower—all updated and delightfully decorated with a nautical touch. The steep shiplap-style staircase (please review photos before booking) leads you to the airy loft bedroom with a full-size bed and direct access to your very own rooftop deck.brThis rooftop deck is truly the highlight of Sand Dollar. Step outside to enjoy panoramic ocean views, salty breezes, and postcard-worthy sunsets shared only with the gulls and the sound of the surf.brbrAs the centrally located cottage in the trio, Sand Dollar offers convenient access to wonderful, shared amenities, including:brA shared deep-water dockbrA pebbly beach area perfect for wading and relaxingbrA shared laundry spacebrbrWhether you're sipping your morning coffee while watching the lobster boats, enjoying an al fresco lunch on the rooftop deck, or taking a stroll to meet your “sister” neighbors on either side, Sand Dollar invites you to unwind and enjoy the simple beauty of Maine's coast.brbrBook your stay at Sand Dollar today... your cozy oceanside escape awaits!brbrPlease note: This property rents Saturday–Saturday in summer. The calendar will display available check-in and check-out options, with the reserved week grayed out.

Couples Cottage at Mackerel Cove - Enjoy your views of Mt. Washington on the Rooftop Deck!

Bailey Island, Maine, United States

Bed

Bath

Sleeps

$270.87

Welcome to Satterthwaite!brbrNestled in the middle of a peaceful dead-end road in a beloved Bailey Island neighborhood, Satterthwaite is a classic New England-style cottage that captures the timeless charm of coastal Maine. While the cottage doesn't offer water views, its exceptional location more than makes up for it! Put on your walking shoes and explore everything that makes Bailey Island so special. Stroll to the dramatic Giant's Stairs walking path for crashing surf and sunrise views, or wander down to Mackerel Cove, where working lobster boats, swimming beaches, and postcard scenery await.brbrInside, this home is the epitome of a Maine cottage. Simple, warm, and full of character. Step through the front door into a spacious living area with comfortable furniture perfect for relaxing after a day of exploring. The living room includes a Smartv, so you can unwind while streaming your favorite shows.brContinue into the charming eat-in kitchen, where you'll find everything, you need to prepare meals during your stay. A half bath is conveniently located on the main floor just off the kitchen.brbrAll four bedrooms are found upstairs, making this home ideal for families or groups:brA large primary bedroom with a king-size bedbrTwo cozy queen bedroomsbrA bright and welcoming twin bedroombrThe full upstairs bathroom includes a stand-up shower.brbrOutside, a newly expanded deck invites you to bask in the sunshine or enjoy an evening breeze. With patio furniture and a charcoal grill, it's the perfect space for casual cookouts, morning coffee, or simply relaxing in the fresh coastal air.brbrAffordable, comfortable, and wonderfully located, Satterthwaite is a welcoming retreat where you can enjoy all that Bailey Island has to offer without breaking the bank.brBook your Maine getaway at Satterthwaite today!brbrPlease note: This property rents Saturday–Saturday during the summer. The calendar will show available check-in/check-out dates. The fireplace is available for renter(s) use.

Charming 4 bedroom Classic Maine Cottage located near the giant stairs.

Bailey Island, Maine, United States

Bed

Bath

7

Sleeps

$323.11

This turn of the century cottage has been lovingly preserved and updated tastefully by our family for 4 generations. Located on Merriconeag Sound, it has easy access from the back yard to the pebbly beach where you can launch your kayak or explore the tidal pools. The wrap around porch is perfect for lounging while watching the spectacular sunsets and listening to the gulls and waves. This is a special place full of old world charm for the whole family to take a break and relax together. brSpecial note for fall travelers: There is a $500.00 fuel charge that you will see in your payment details. However, whatever fuel you do not use , the amount will be refunded to you within 30 days after your stay.

Authentic maine cottage with direct water frontage

Bailey Island, Maine, United States

Bed

Bath

Sleeps

$504.38

The Johnson Homestead is located on the south end of Bailey Island looking out at the entrance to Mackerel Cove. With one level access to 4 bedrooms and 2 full baths, front and back yards, this is the perfect place to unwind with easy accessibility. Sleeping 6-8(MAX), the house will be a comfortable fit for anyone wanting an ocean view from the living room couch or a chair in the front yard. Sit and watch the daily sunsets coloring the sky, they don't disappoint. Many days you will see Mt Washington on the horizon in the west as the sun sets, bringing the ocean view to a mountain view. brbrA short walk through the back yard will bring you to a semi private beach in tranquil Little Harbor. At the beach you may enjoy peaceful moments watching the sunrise, swimming, floating, kayaking, or exploring the ocean floor's tide pools. The high and low tides makes a walk to the beach a different adventure every day, that's part of Maine life! brbrThe Johnson Homestead has central heat and AC. The bedrooms have: 1 Bedroom with King Bed, 2 bedrooms with Queen Beds, 1 bedroom with 2 Twins, Linens provided. There are two full bathrooms, one with walk in shower and one with a tub/shower, towels provided. The fully stocked kitchen has a eat in dining table with 6 chairs. There is a full sized washer and dryer. A gas grill for cooking out is provided. If you're hungry for local flavor in a Do-it-Yourself fashion pick up some fresh off the boat lobsters, cook them up yourself and eat them at the backyard picnic table. Delicious!brbrThere is a sun porch on the eastern, backside of the home. Enjoy eating meals, reading a book, playing games, or just watch the children play in the back yard. brbrThere is an automatic generator provided at the home.brbrWe recommend exploring local gift shops, restaurants, and ice cream stands right here in Harpswell. If you would like to explore more of Midcoast Maine check out museums and the Maine State Music Theatre at Bowdoin College in Brunswick, Bath Maritime Museum, or the famous LL Bean store and outlet shopping in Freeport, Maine. brbrA few of the local Harpswell restaurants we recommend within a 5-30 minute drive: Cook's Lobster & Ale House, Sundrenched, Bailey Island General Store (BIGS), Salt Cod Cafe and Island Candy Company. Erica's Seafood, Dolphin Restaurant and Marina, Pammy's Ice Cream, and Uncle Pete's Community Market. Please confirm hours before arrival for seasonal days and hours.brbrWe recommend a car for your stay here in Harpswell, Johnson Homestead is located 25 minutes from major grocery stores and the town of Brunswick. We hope you will be able to enjoy exploring all the Maine coast has to offer. If you will be flying to Maine we recommend Portland International Jetport (PWM). If assistance is needed for varying flight arrivals of your party, Safe Harbour Property Management offers concierge rides to and from PWM, please inquire.brbrKayak rental and rate inquiries may be found at:brSeaspray Kayaking 207-404-1100brRIngs Marine Service 207-865-6143brbrbrbrbrbrbrbrbrbrbrbr

Johnson Homestead. One level living, ocean view with semi-private beach access.

Bailey Island, Maine, United States

Bed

Bath

8

Sleeps

$397.76

Welcome to Lobster Ledge!brbrEscape to the beauty of Bailey Island and enjoy relaxing coastal living in this charming two-bedroom vacation rental overlooking the sparkling waters of Casco Bay. Perfect for couples, small families, or a peaceful friends' retreat, this inviting home offers the ideal setting to unwind and take in Maine's breathtaking seaside scenery.brbrWake up to ocean views and the fresh salt air from the comfort of the primary bedroom featuring a cozy queen-size bed. The second bedroom offers two twin beds, making it a great space for children or additional guests.brbrStart your mornings with coffee or wind down in the evenings on the covered porch while enjoying sweeping views of Casco Bay. Outside, a private gazebo provides the perfect spot for al fresco dining, reading a good book, or simply soaking in the peaceful coastal surroundings.brbrWhether you're exploring the island, enjoying nearby beaches, or just relaxing by the water, this Bailey Island retreat offers a quiet and comfortable home base for your Maine vacation.

Charming Bailey Island Coastal Getaway with Stunning Casco Bay Views.

Bailey Island, Maine, United States

Bed

Bath

Sleeps

$346.04

Welcome to beautiful Briar Rose!brPerched in the heart of beautiful Bailey Island, this inviting coastal retreat offers the perfect blend of comfort, convenience, and classic Maine charm. With sweeping ocean views and a location just a short stroll from the island's beloved restaurants, shops, and scenic spots, it's an ideal getaway for couples, families, or small groups looking to experience the best of the coast.brInside, the home features a bright and airy open-concept living, dining, and kitchen area designed for easy gathering and relaxation. Large windows invite in natural light and showcase glimpses of the sparkling water, while the comfortable living space provides the perfect place to unwind after a day exploring the island. The fully equipped kitchen flows seamlessly into the dining area, making it easy to prepare meals and enjoy time together.brThe home includes two comfortable bedrooms and two full bathrooms, offering privacy and convenience for guests. Whether you're waking up to the salty ocean breeze or winding down after a sunset walk along the shore, each space is thoughtfully designed for a restful stay. Air conditioning ensures comfort during warm summer days.brStep outside and enjoy the relaxed pace of island life. From the property, you can walk to Bailey Island's favorite waterfront restaurants, lobster pounds and scenic harbors, making it easy to enjoy fresh seafood, coastal views, and the authentic charm of this historic fishing village.brWhether you're sipping morning coffee while taking in the ocean views, exploring nearby coastal trails, or enjoying dinner by the water, this Bailey Island vacation rental offers a perfect home base for an unforgettable Maine coast escape. brbr **PLEASE NOTE** The owners of the property stay at the house behind this rental for the summer.

In the heart of beautiful Bailey Island, this coastal retreat offers a blend of comfort and charm.

Bailey Island, Maine, United States

Bed

Bath

Sleeps

$772.34

The Historic Captain York House in a unique New England home that was originally one home built along side another. This allows for the house to split into a duplex. The historic Captain York House has been on Bailey Island for more than 100 years. It is a 7 bedroom, 7 bathroom house that can accommodate families of up to 12 adults. brALL SUMMER RENTALS ARE SATURDAY TO SATURDAY - NO EXCEPTIONSbrThis house provides a great home base for exploring Bailey Island and the surrounding coastal areas. With 7 bedrooms and 7 baths everyone has their own area! Beds include: two king, two queen, one full trundle with twin, twin bunk beds, and two twins. brSheets, linens and towels included in linen closet - beds are not made. We have board games throughout the house and a mini foosball, ping-pong, air-hockey, pool table. brThere are many outdoor activities on and within a short drive, including; beaches, boating, kayaking, hiking trails, Bailey Island General Store, Land's End Gift Shop, Cook's Lobster and Ale House, and Morse's Cribstone Restaurant on the island (with both restaurants in walking distance). Come explore, relax and enjoy the Maine coast! brbrThere are absolutely no pets allowed at this property. There are two external cameras monitoring the driveway and road. If a pet is seen at the property your party will be asked to remove the pet the same day. If this is not done your reservation will be forfeited and your entire party will be asked to leave immediately. We appreciate it when our property is treated like your own, with respect to its owner’s house rules.brbr*** Please note, upon booking you will be asked to sign a contract agreeing to all house rules. Your reservation will not be confirmed until this is received ***

The Captain York House

Bailey Island, Maine, United States

Bed

Bath

Sleeps

$461.69

Welcome to Ole Greeley Cottage, a charming, classic Maine cottage with stunning ocean views over Merriconeag Sound. You'll love waking up to the sights and sounds of the ocean, exploring Harpswell and the surrounding towns and retreating to the cottage to catch the gorgeous Bailey Island sunset paint the sky with red, orange and purple from the wrap-around covered porch. Don't miss the opportunity to dine al fresco on the water's edge at the outdoor picnic table that seats 8, and a two person bistro set. brbrInside the cottage you'll find an open concept kitchen, living, and dining area with many windows and a sliding glass door opening to the ocean and covered porch. The kitchen offers a farmhouse sink, large retro refrigerator, gas range, microwave and all the cooking/dining ware needed to prepare and enjoy a delicious homecooked meal. The dining table seats 4-6 and the living room offers a large leather sofa and two wicker chairs, the perfect spot to read a book, play a game, or delight in conversation with friends. The owners have shared with guests a broad collection of books, puzzles, and board games, inviting all to relax and enjoy the slow-pace of island life.brbrLocated on Garrison Cove Road on Bailey Island, guests will love the ability to walk to Cook's Lobster & Ale House just down the road, as well as Cook's Wharf offering lobster fresh off the boat. Step off the dock onto the Schooner Alert for a sunset cruise around the islands or watch the lobstermen and sailboats cruise by from the porch. The cottage is also just a short walk/drive away from Cedar Beach, The Bailey Island General Store, Fishnet Cafe, Land's End Gift Shop, Sundrenched restaurant, Historic Cribstone Bridge, Salt Cod Cafe, H2Outfitters for kayak rentals/tours, and so much more! brbrCome to Ole Greeley Cottage and enjoy all Bailey Island and Harpswell have to offer. We're sure it will beckon you back for years to come!brbrOle Greeley Cottage is pet-friendly (2 maximum, well behaved), a non-refundable pet fee does apply.brbrPlease note - Although recently renovated/updated, the cottage was originally built in the early 1900's and the interior walls dividing the bedrooms are thin/not insulated, allowing sound to travel more easily than a modern home. Also, the primary bedroom has a custom headboard that is open to the stairs to the first floor. We hope this information is helpful as you prepare for your stay at this charming cottage!brbrImportant Information Regarding Water UsagebrDue to the proximity to the beautiful, rocky coast, the water supply for the cottage is a water storage tank rather than a traditional well. Water is delivered to the property on a regular basis, but guests should be particularly aware of their water consumption and make every effort to conserve this precious resource. While you may use the water comfortably, we ask that you please not run water unnecessarily (i.e. keeping showers brief, turning water off while brushing teeth, not running water constantly while doing dishes, etc.).brbrBedrooms:br2nd Floor:brPrimary BR- Queen Bed with Ocean ViewsbrSecond BR- Double Bed with peeks of the OceanbrThird BR- Twin Bed with peeks of the OceanbrbrBathrooms:br1st Floor:brFull BA with medium sized shower/tub combobrbrAir Conditioning: NobrWater Access: Direct, on property via private stairsbrBeach Towels: Not includedbrDeparture Cleaning: IncludedbrClosest Shopping Village: Brunswick, 15min awaybrCoffee Maker: Yes, Regular DripbrDishwasher: NobrGrill: Gas Grill available, Propane providedbrHeat Source: Propane Heat Stove on 1st Floor, controlled by thermostatbrInternet Access: Yes, Xfinity Cable Internet and WiFibrLinens & Bath Towels: IncludedbrLobster Pot: YesbrOutdoor Firepit: NobrParking: 1-2 carsbrTrash Removal: IncludedbrTV: No (guests are welcome to bring their own laptops/ipads to connect to the internet for tv/streaming entertainment)brWasher & Dryer: No, laundromats nearby in Brunswick 15-20 min awaybrWater Frontage: Direct ocean frontagebrWater Source: Water tank, bottled drinking water recommended

Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage

Bailey Island, Maine, United States

Bed

Bath

Sleeps

$247.21

Welcome to Goldsmith Apartment!brbrEscape to the serene beauty of coastal Maine at Goldsmith Apartment, a charming studio garage apartment perched right on Harpswell Sound. This cozy retreat offers breathtaking sunset views over the Atlantic, making it the perfect setting for a romantic getaway or a peaceful escape by the water. While the shoreline here is rocky and steep, so it's not ideal for swimming, it provides an excellent vantage point to watch the waves, study the tides, and enjoy the mesmerizing ocean vistas up close.brbrInside, the apartment features an open-concept layout designed for comfort and ease. The galley-style kitchen is perfect for preparing simple meals, which you can enjoy at the four-person dining table. The living area includes two cozy armchairs positioned to take full advantage of the water views, a TV for quiet nights in, and a queen-size futon that can serve as an extra sleeping space if needed. The apartment also includes a full bathroom with a stand-up shower and a private balcony that looks directly out over the open ocean, ideal for morning coffee, sunset cocktails, or simply savoring the coastal air.brbrLocated in the heart of Bailey Island, Goldsmith Apartment provides easy walking access to local shops, walking paths, and scenic areas. The island's unique charm and natural beauty are right at your doorstep, making it simple to explore the coastline, stroll along quiet paths, or visit nearby landmarks.brbrWhether you're celebrating a special occasion, seeking a romantic retreat, or just longing for a peaceful seaside escape, Goldsmith Apartment offers a cozy, intimate, and unforgettable Maine getaway.

Apartment

Perfect spot for a couples get-away, ocean views from the balcony and sitting area

Bailey Island, Maine, United States

Bed

Bath

Sleeps

$286.51

Welcome to Blue Heron!brBreathe in the fresh Atlantic air and start your day with easterly sunrise views from the spacious upstairs deck, complete with comfortable outdoor seating perfect for morning coffee, or relaxed dinners. With a generous yard for kids to play and the water access just 300 feet from the house, Blue Heron offers the ideal setting for simple seaside living. Prefer a broader stretch of sand Picturesque Cedar Beach is just moments away.brStep inside this charming two-level cottage and feel immediately at home.brbrThe entry level features two inviting bedrooms. One with a queen bed and the other with two twin beds, along with a full bathroom equipped with a stand-up shower.brHead upstairs to the heart of the home, where panoramic ocean views greet you the moment you arrive. The cozy, well-appointed kitchen offers everything you need, including a convenient eat-in dining area. The bright, open living room provides additional sleeping space thanks to a comfortable pull-out bed, making the home perfect for families or small groups. Sliding doors lead directly to the upper deck, where fresh ocean breezes and sweeping views set the tone for a memorable stay.brbrExplore the Local AreabrbrBlue Heron places you close to the best of the surrounding coastal community. Spend your days beachcombing, swimming, or strolling along shoreline paths. Local markets, seafood shacks, and family-friendly restaurants are a short drive away, as are nature trails, scenic overlooks, and opportunities for kayaking, and wildlife watching. Whether you're seeking relaxation or adventure, you'll find it within easy reach.brbrPlease Note:brThis property rents Saturday to Saturday during the summer season. The booking calendar will display available check-in and check-out dates; the week between them will appear grayed out.

Classic Maine Cottage with astonishing views located within walking distance to Cedar Beach!

Bailey Island, Maine, United States

Bed

Bath

Sleeps

$558.44

Welcome to West Shore House!brbrPerched high on a scenic hillside overlooking the sparkling waters of Casco Bay, West Shore House offers some of the most captivating sunset views on Harpswell Sound. With its elevated vantage point, wrap-around deck, and two private balcony decks, this cottage ensures you never miss the evening sky as it glows in shades of gold and pink over the bay. Set along peaceful West Shore Road, the home provides a perfect blend of serenity and convenience, enjoy quiet coastal living while still being within walking distance of the island's general store and local restaurants.brbrEnter through the lower level, where you'll find a washer and dryer for your convenience, along with extra storage space. Head upstairs to the main living floor, where light pours into the open-concept layout. A well-equipped kitchen makes cooking a pleasure, and the adjacent sitting area is the perfect spot for morning coffee. The dining and living rooms offer plenty of comfortable seating, and with direct access to the expansive wrap-around deck, indoor and outdoor living flow together seamlessly. A full bathroom is also located on this level.brbrContinue to the top floor to find two inviting bedrooms, each designed to maximize comfort and the views. The primary bedroom features a king-size bed, a spacious closet, an ensuite bathroom, and its own private balcony overlooking the water, ideal for a quiet sunrise or a peaceful sunset moment. The second bedroom offers two twin beds, a half bath, and a private water-facing balcony of its own.brbrWhether you're sipping a glass of wine on the deck, strolling along the shoreline, exploring the island on foot, or cozying up by the fireplace on a cool evening, West Shore House offers a quintessential Maine experience from a stunning hilltop perch.brbrCome enjoy the coastal charm and unforgettable views of West Shore House, your perfect retreat on Casco Bay.brbrPlease note: This property rents Saturday–Saturday in summer. The calendar will reflect available check-in/check-out days, and the week in between will be grayed out. Fireplace is available for renter(s) use.

Enjoy spectacular sunset and water views from the deck and balconies with water access.

Bailey Island, Maine, United States

Bed

Bath

6

Sleeps

$839.3

The well-appointed Captain Lawrence E. Johnson House is available for weekly rentals during the summer season and two-night-minimum stays in the off-season. The house is also available year-round for retreats, reunions, and special events.brbrOperated as Maine Island Getaway, with additional photos, seasonal notes, and property details available at maineislandgetaway.com, this luxury island home on Bailey Island offers beautiful water views from nearly every room, framed by working harbors and the timeless calm of island life. While the house is not directly on the shoreline, it sits in a village-like setting with spacious private decks and yards, along with nearby water access for swimming and boat launching.brbrThe home features four luxury bedrooms with flexible accommodations, each with an en-suite bathroom, a modern professional kitchen, generous dining and comfortable living spaces, and a fully equipped media room. Guests enjoy high-speed fiber-optic internet—fast, reliable, and ideal for remote work or streaming, as well as energy-efficient central heating and air conditioning in all bedrooms.brbrFurnished with art and antiques that quietly set the tone of a true captain’s home, the house is authentic, functional, and quietly refined—every detail considered, every choice rooted in place.brbrEnjoy all that Bailey Island and neighboring Orr's Island have to offer: exceptionally fresh lobster, an easy walk to secluded Cedar Beach, hikes to the dramatic Giant’s Stairs, kayak rentals just over the Cribstone Bridge at H2O Outfitters, or fishing and sailing charters with experienced local skippers.brbrThe house is fully furnished and thoughtfully equipped, ready for your enjoyment from the moment you arrive.brbrKeywords: House · Maine Island Getaway · Custom Amenities · Ocean Views

Amazing Views, and Comfortable Spaces in this Well Appointed Island Home

Bailey Island, Maine, United States

6

Bed

5

Bath

14

Sleeps

$607.55

Friendly Cottage on Oceanside, Bailey Island is now available for your seaside vacation, no matter the season. This well-insulated cottage, heated and cooled by solar and geothermal systems, is appealing during the less - crowded brisk Maine springs, the lazy ocean-breezed days of summer, the colorful crisp days of fall, or the quiet peaceful days of winter.br Friendly cottage is on the east side of the island with an unhindered view of Casco Bay and spectacular sunrises, and sits on a secluded beach at the dead end of a quiet neighborhood.br Yet, the cottage is in walking distance of the local general store, post office, a non-denominational church, several local eateries including the famous Cook's Lobster House as well as Mackerel Cove, the hub of the fishing and boating community. Entertaining and socializing has a comfortable flow in this 3 bedroom-2 bathroom home - perfect for family get-togethers, reunions, special events or simply a nest to enjoy the Maine experience. The nearest shopping centers are in Brunswick (13 miles away and a 30 minute drive). Stopping at a grocery store before you come to Bailey Island might be more convenient, although there is a general store with limited supplies. brFriendly Cottage is an excellent example of a home built with many innovative technologies including solar hot water panels and geothermal, just to name a few. If you are considering building an energy efficient home with all or some of these technologies, come for a stay! brCheck out our other rental Ocean Breeze Cottage Home Away # 3001385.brbrKeywords: New Bailey Island Cottage on the Ocean with Beach

Spacious Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

Bailey Island, Maine, United States

Bed

Bath

Sleeps

$650.3

Welcome to Captain's Watch!brbrPerched on the rugged cliffs of beautiful Bailey Island, this charming 2-bedroom, 1-bath Maine vacation getaway offers breathtaking easterly views of Casco Bay, where you can enjoy spectacular sunrises over the Atlantic each morning.brbrInside, the home features a warm and inviting living space complete with a cozy fireplace, perfect for relaxing after a day of exploring the coast. Air conditioning ensures your comfort during the warmer summer months, while large ocean-facing windows bring in natural light and stunning water views throughout the day.brbrStep outside onto the expansive oceanfront deck, ideal for sipping your morning coffee as the sun rises, dining al fresco with family and friends, or simply unwinding to the soothing sounds of the waves below.brbrConveniently located in the heart of Bailey Island, this property is within easy walking distance to the iconic Land's End Gift Shop and nearby beach access, allowing you to enjoy local shopping, scenic strolls, and the natural beauty of Maine's coastline without ever needing to get in the car.brbrWhether you're planning a peaceful retreat or a memorable seaside getaway, this cliffside escape offers the perfect blend of comfort, location, and unforgettable ocean views. brPLEASE NOTE: FIREPLACE IS NOT FOR TENANT'S USE!

Perched on the rugged cliffs of beautiful Bailey Island.

Bailey Island, Maine, United States

Bed

Bath

Sleeps

$539.62

Welcome to your perfect coastal escape at Puffin's Perch on beautiful Bailey Island where classic Maine charm meets sweeping easterly ocean views.brbrPerched along the rugged shoreline, this inviting waterfront retreat captures breathtaking sunrises over the Atlantic and uninterrupted views of open ocean. Wake early to golden light spilling across the water, watch lobster boats head out with the morning tide, and enjoy the peaceful rhythm of the sea throughout the day.brbrProperty HighlightsbrExpansive easterly-facing ocean viewsbrFront-row seats to spectacular Atlantic sunrisesbrSpacious deck perfect for morning coffee by the seabrBright, open-concept living space filled with natural lightbrFully equipped kitchenbrComfortable bedrooms with crisp linensbrHigh-speed WiFibrLarge windows frame the ever-changing seascape, bringing the outdoors in and filling the home with beautiful morning light. The open living and dining area creates a welcoming gathering space, ideal for relaxing after a day of exploring Maine's coast. There are two bedrooms and a full bathroom in this quaint cottage all with modern amenties.brbrLocated just minutes from the iconic Cribstone Bridge, the home offers convenient access to kayaking, scenic coastal walks, and fresh lobster right off the boat. Explore nearby Brunswick for charming shops and dining, or spend the day discovering tidal pools and quiet coves along Bailey Island's rocky shoreline.brbrKnown for its working waterfront and unspoiled beauty, Bailey Island offers a peaceful retreat away from crowds. Here, mornings are the main event glowing skies, salty air, and the sound of waves set the tone for a truly restorative getaway.brbrThis rental delivers an unforgettable Maine experience — where every morning begins with a stunning Atlantic sunrise and the beauty of the coast right outside your door.

Wake to spectacular easterly ocean views and unforgettable Atlantic sunrises.

Bailey Island, Maine, United States

Bed

Bath

Sleeps

$509.49

Welcome to Coastal Breezes!brIf you're looking for the perfect Maine family getaway you've come to the right place. This historic home is the second oldest home on Bailey Island. Though you would never know it upon stepping inside. It has lovingly been restored and maintained through the years while at the same time keeping true to its roots.brCoastal Breezes (also known as the Captain William Henry Sinnett house) rests on almost half an acre towards the end of Bailey Island. With four bedrooms and one and a half baths this house is the perfect spot for small or large families alike. There are countless amenities within the property and nearby.brLooking to take it easy at home Sit on your large deck with a view of the ocean to enjoy a meal from a local restaurant or cooked in your well-equipped kitchen. This house is well stocked with board games, puzzles, and outdoor games. High speed internet and smart TVs throughout.brLooking to take a walk to the water Head right down the street to the world famous Giant's Stairs located on the coast of the open Atlantic Ocean. This amazing coastal landmark was donated by the prior owner of this house. It includes sights, sounds, and paths to explore.brLooking to go to the beach Grab your lunch, beach chairs and towels and head down to Mackerel Cove and watch the working lobster boats haul their traps.brClose enough to all local amenities, we are certain Coastal Breezes is the perfect Maine vacation for you and yours. brPlease note: Fireplaces are not for use by renters. This home includes some original period details throughout, including some sloping floors which add charm but mentioning for those with mobility issues.

Historic home located on Bailey Island within walking distance to the Giant's Stairs.

Bailey Island, Maine, United States

Bed

Bath

Sleeps

$490.88