Vacation Rentals By Owner In Bailey Island, ME

Completely renovated from the foundation up and completed in August 2011, Homeport boasts a modern design that allows you to take in stunning views of Mackerel Cove and its beach. Nestled among family-owned properties passed down through generations of lobstermen, this home enjoys a prime location on Bailey Island, just a short walk from the Bailey Island General Store, Land's End Gift Shop, and several beaches. With breathtaking sunsets and the feeling of being surrounded by water, you'll truly experience the essence of a Maine coast getaway. The picturesque views of Mackerel Cove’s waterfront stretch across anchored boats and lobster docks, leading out to the open ocean. Cool ocean breezes gently transition hot summer days into peaceful, starry nights.brbrThis idyllic setting is perfect for exploring Maine’s renowned rocky coast before returning to the comfort of your home at the end of the day. A convenient boardwalk behind the house leads to a semi-private sandy beach, perfect for searching for sea glass and shells or enjoying a swim. Homeport will undoubtedly leave a lasting impression, drawing you back year after year to create new memories along the beautiful Maine coast.brbrSorry, guest pets are prohibited. If you have pet allergies, please contact MaineStay Vacations for more information prior to booking.brbrBed types/descriptions:brFirst Floor Master- Queen BedbrSecond Floor Master- Queen BedbrSecond Floor Third Bedroom- Twin over Queen Bunk Bed.brbrBathroom setup/description: brFirst Floor- Full with Shower and LaundrybrSecond Floor- Full Shower/Tub CombobrbrAir Conditioning: Window AC units in bedroomsbrBeach Access: Direct, on property via semi-private boardwalkbrBeach Towels: Not includedbrDeparture Cleaning: IncludedbrCable TV: Yes, in Living roombrClosest Shopping Village: Brunswick, 20min awaybrCoffee Maker: Yes, automatic dripbrDishwasher: YesbrGrill: Gas Grill available, Propane providedbrHeat Source: Hot Water Baseboard Heat (Propane)brInternet Access: Yes, Xfinity Cable Internet and WiFibrLinens & Bath Towels: Included, beds are made prior to guest arrival and towels remain in their sanitized packaging, placed on each bedbrLobster Pot: YesbrOutdoor Firepit: NobrParking: 1-2 cars, some overflow available, please ask manager for detailsbrStairs to Water: N/A, Semi-private access to Back Beach via boardwalk and public access for Mackerel CovebrTrash Removal: Included, picked up weekly (for multi-week stays) or upon departurebrTV: TV in Living RoombrUsable Fireplaces: NobrWasher & Dryer: Yes, located in first floor bedroombrWater Frontage: Direct access to semi-private Back Beach and public access to Mackerel CovebrWater Source: Well water with filtration/softener system, bottled drinking water recommended

Homeport - Modern oceanfront cottage overlooking quintessential Mackerel Cove

Bailey Island, Maine, United States

Bed

Bath

Sleeps

$197.67

Welcome to The Studio!brbrPerched on Tip-Top Hillside, this charming single-story cottage offers picturesque views of Mackerel Cove and the surrounding coastline. Spend your mornings or evenings on the spacious deck, watching the lobstermen navigate the cove, or take a leisurely walk down the wooded path to the shared dock and water's edge for a closer connection to the Maine coast.brbrDesigned with one level living in mind, The Studio combines convenience with classic Maine charm. Step inside to a well-equipped kitchen that flows seamlessly into the open dining and living area, where you can enjoy limited water views, cable TV, and wireless internet. For cozy family or game nights, board games and playing cards are also provided.brbrThe cottage features two comfortable bedrooms, each with ample closet space for your belongings. One bedroom offers a queen bed, while the second has a twin and double bed, perfect for children or extra guests. A full bathroom is located conveniently off the bedrooms.brbrWith its deck, shared dock, and prime location on Tip-Top Hillside, The Studio is the perfect getaway to enjoy the charm and beauty of Mackerel Cove.brbrPlease note: This property rents Saturday-Saturday in summer. The calendar will show available check-in/check-out days; the week in between will be grayed out.

Cozy 2 bedroom cottage with beautiful views of Mackerel Cove!

Bailey Island, Maine, United States

2

Bed

Bath

5

Sleeps

$475.95

Resting on the beautiful, rugged Bailey Island coastline is this well-appointed 2BR, 1 BA cottage offering stunning ocean views, a spacious lawn, patio, and A/C for warm summer days. You'll love exploring the neighborhood, as well as the local restaurants and shops during the day and returning to the comforts of the cottage in the evenings to relax and soak in the sights and sounds of the ocean.brbrInside the cottage you'll find a well-equipped kitchen with all you'll need to cook, a sitting area for 4, dining table, and two chairs overlooking the water. The full bathroom located on the first floor offers a large tile and glass shower. Upstairs, there are two ocean view bedrooms, one with a queen bed and the other with a twin trundle bed, both opening to a shared balcony.brbrOutside, guests will enjoy a patio with a picnic table for dining outdoors, as well as a yard with adirondack chairs perched overlooking the bay and ledges. brbrBook your stay at Sea Spray today and enjoy all the Harpswell Islands have to offer! The sea-breeze and stunning sunrises will beckon you back for years to come! brbrTesla Car Charger Included!brbrAir Conditioning: Yes, via heat pumps on first and second floorsbrBeach/Water Access: Direct, on property, sandy/rocky/pebbly shorelinebrBeach Towels: Not includedbrDeparture Cleaning: IncludedbrCable TV: Cable TV in Living Room and Queen BedroombrClosest Shopping Village: Brunswick, 20min awaybrCoffee Maker: Yes, automatic drip coffee makerbrDishwasher: YesbrGrill: Gas Grill available, Propane providedbrHeat Source: Heat PumpsbrInternet Access: Yes, Xfinity Cable Internet and WiFibrLinens & Bath Towels: Included, beds are made prior to guest arrival and towels remain in their sanitized packaging, placed on each bedbrLobster Pot: YesbrOutdoor Firepit: NobrParking: 2 carsbrStairs to Water: No stairsbrTrash Removal: Included, picked up weekly (for multi-week stays) or upon departurebrTV: TV in Living Room and Queen BedroombrUsable Fireplaces: NobrWasher & Dryer: Yes, located in the basement (access is on the backside of the house)brWater Frontage: Direct ocean frontagebrWater Source: Well water with filtration/softener system, bottled drinking water recommended

Sea Spray - Beautiful 2BR, 1BA cottage with expansive views of Casco Bay

Bailey Island, Maine, United States

Bed

Bath

Sleeps

$817.91

Perched on the water's edge, The Overlook offers commanding views of Merriconeag Sound to Casco Bay and its islands. You'll find yourself waiting to watch the sunset every evening, as the sky is painted with stunning hues and the soft light fills every room. The Overlook offers multiple decks with plenty of seating for dining outdoors or simply relaxing by the sea. Beautiful gardens and trees surround the property, offering great privacy, while being within walking distance to all Bailey Island has to offer.brbrInside you'll find a well appointed kitchen with everything you'll need to prepare a delicious Maine meal, a beautiful dining room area with two sliding glass doors opening to the deck, and a spacious living room with comfortable furnishings and panoramic ocean view. The first floor also offers a bedroom with a queen bed and ocean views, as well as a full bathroom with a laundry area just outside. On the second floor you'll find two additional ocean view bedrooms with queen beds and a shared full bathroom with a tile shower. Hardwood and tile floors throughout, modern coastal decor, and an abundance of natural light completes this seaside retreat.brbrConveniently located in the West Shore neighborhood of Bailey Island, you'll love being just 0.5mi (8-10min walk) from all of the island's great local restaurants including Cook's Lobster & Ale House (serving lunch and dinner), Sundrenched (serving lunch and dinner), and Bailey Island General Store (convenience store).brbrSpend your days relaxing by the sea, exploring the shore, sailing out of Cook's Lobster on the Schooner Alert (70-foot tall ship), or soaking up the sun at Cedar Beach (1mi away) and come home to experience the gorgeous sunset over the bay.brbrThe Overlook is the perfect vacation destination and will surely have you coming back for years to come.brbrSorry, pets are not allowed at The Overlook.brbrBed types/descriptions:brFirst Floor-brBedroom with Queen Bed, Closet, and Ocean ViewsbrSecond Floor-brMaster Bedroom with Queen Bed, Closet, and Ocean ViewsbrBedroom with Queen Bed, Closet, and Ocean ViewsbrbrBathroom setup/description: brFirst Floor- Full Bath with Shower/Tub CombobrSecond Floor- Full Bath with Tile ShowerbrbrbrAir Conditioning: NobrBeach/Water Access: Direct, on property via private stairs, rocky/pebbly shorelinebrBeach Towels: Not includedbrDeparture Cleaning: IncludedbrCable TV: Uses Xfinity Stream app on TV for cable entertainment channels, Xumo Play app for Live streaming news channelsbrClosest Shopping Village: Brunswick, 20min awaybrCoffee Maker: Yes, regular drip brDishwasher: YesbrGrill: Gas Grill available, Propane providedbrHeat Source: Forced hot air brInternet Access: Yes, Xfinity Cable Internet and WiFibrLinens & Bath Towels: Included, beds are made prior to guest arrival and towels remain in their sanitized packaging, placed on each bedbrLobster Pot: YesbrOutdoor Firepit: NobrParking: 2 carsbrStairs to Water: YesbrTrash Removal: Included, picked up weekly (for multi-week stays) or upon departurebrTV: Smart TV in Living RoombrUsable Fireplaces: No (woodstove in house is NOT for guest use)brWasher & Dryer: Yes, located first floorbrWater Frontage: Direct ocean frontagebrWater Source: Well water with filtration/softener system, bottled drinking water recommended

The Overlook- Enjoy stunning sunsets from this well-appointed Bailey Isl home

Bailey Island, Maine, United States

Bed

Bath

Sleeps

$448.71

Little Harbor – A True Maine EscapebrbrNestled on the pristine shores of Bailey Island, this cozy yet rustic oceanfront cottage offers the ultimate Maine experience. Surrounded by bold surf and spectacular views from every window, the cottage overlooks what was once called the most spectacular view in North America.brbrTo the east and south, you’ll find sweeping open ocean vistas of Casco Bay, while to the west, the charm of Little Harbor unfolds and Ragged Island is just beyond the horizon. Whether you're dining inside, sunbathing on the spacious deck, or simply relaxing as the waves crash on the rocks below, the serene surroundings promise a deeply restful retreat.brbrThe cottage comfortably sleeps four, with close proximity to scenic walking trails and public beaches. It’s just 25 minutes from the Maine State Music Theatre at Bowdoin College, local art galleries, and the Mere Creek Golf Club. For adventure seekers, there are charter fishing trips, kayak rentals, whale watching, and Casco Bay tours nearby.brbrWhether you choose to unwind on the deck or explore the beauty of the area, you’ll be captivated by the rolling waves, soothing surf, and breathtaking sunrises and sunsets. For those who love Maine, or those experiencing it for the first time, this cottage offers a truly unforgettable escape.brbrCome experience the magic of the rockbound coast of Maine – it doesn’t get any better than this.brbrbrBed types/descriptions:brMaster Bedroom with Queen BedbrSecond Bedroom with Full BedbrbrBathroom setup/description: brFull bath with Shower StallbrbrAir Conditioning: NobrBeach Access: N/A, Water Access via LedgesbrBeach Towels: Not includedbrDeparture Cleaning: IncludedbrDock & Float: NobrCable TV: No Cable, Smart TV with Streaming Only in Living roombrClosest Shopping Village: Brunswick, 25min awaybrCoffee Maker: Yes, automatic dripbrDishwasher: NobrGrill: Gas Grill available, Propane providedbrHeat Source: Wood Stove in Living Room (primary heat source, wood provided), Electric Baseboard in Bathroom, and Space Heaters available.brInternet Access: Yes, Fidium Internet and WiFibrLinens & Bath Towels: Included, beds are made prior to guest arrival and towels remain in their sanitized packaging, placed on each bedbrLobster Pot: YesbrOutdoor Firepit: NobrParking: 1-2 carsbrStairs to Water: No, Water Access via LedgesbrTrash Removal: Included, picked up weekly (for multi-week stays) or upon departurebrTV: Yes, in Living RoombrUsable Fireplaces: No, Wood StovebrWasher & Dryer: NobrWater Frontage: Yes, Direct Water FrontagebrWater Source: Well water with filtration/softener system, bottled drinking water recommended

Little Harbor - Crashing surf, sunrise views from this perfect Maine getaway.

Bailey Island, Maine, United States

Bed

Bath

Sleeps

$314.82

Welcome to Giffin Log Cabin!brbrDiscover the charm, comfort, and serenity of coastal Maine at Giffin Log Cabin. A warm and welcoming 3-bedroom, 2-bathroom retreat tucked just over a hill along Bailey Island's beautiful rocky western shore. With expansive water views, a spacious deck, and a peaceful screened-in porch, this well-maintained log home offers the perfect blend of rustic character and modern relaxation.brbrStep outside and you'll find a well-kept path leading to the rocky shoreline, where you can gaze out past Mark Island Monument and into Mackerel Cove. Whether you're hunting for sea treasures, watching the boats pass, or simply enjoying the salty breeze, this shoreline access makes every day a little more magical. The large yard provides plenty of room for outdoor fun such as picnics, lawn games, or quiet afternoons reading beneath the open sky.brbrLocated on picturesque Bailey Island, the cabin sits within walking distance of a charming little beach, a wonderful gift shop, and the popular scenic destination known as Land's End. Stretching roughly 2.5 miles long, the island offers beaches, walking paths, a general store, post office, and three restaurants, all just minutes away.brbrA Cozy & Comfortable InteriorbrInside, Giffin Log Cabin is thoughtfully designed for easy living:brMain LevelbrEnter through the well-equipped kitchen, complete with everything you need to prepare meals at home. A small breakfast table makes morning coffee and quick bites a breeze.brThrough one door, step into the dining room, where a piano adds a touch of charm and large windows look out toward the deck and treetops. Through the opposite direction, you'll find the first-floor bathroom with a tub/shower combo and a first-floor bedroom featuring a comfortable queen-size bed.brBoth the dining room and the hallway near the bedroom lead into the spacious living room, where plenty of seating ensures everyone can gather comfortably. From here, step directly onto the screened-in porch, one of the home's most inviting spaces. Outfitted with cozy wicker furniture, soft cushions, and a picnic table, it's the perfect place to enjoy meals, play games, or simply relax while taking in the filtered views of the water. The porch opens to a lovely deck complete with a gas grill for your use.brbrUpstairs RetreatbrClimb the stairs to find two bright, cheerful bedrooms:brLeft Bedroom: Includes a queen-size bed and beautiful water views.brRight Bedroom: Offers a queen-size bed plus a twin trundle. Ideal for families or groups needing flexible sleeping arrangements.brA shared bathroom connects both rooms, offering dual access and a stand-up shower. The tranquil ocean views from both bedrooms make waking up here a true delight.brbrAdditional AmenitiesbrA washer and dryer are available in the basement for guest use.brWater views can be enjoyed from several rooms throughout the home.brThe home balances rustic log-cabin charm with clean, comfortable living spaces perfect for year-round enjoyment.brbrWhether you're seeking peaceful solitude, family adventures, or the quintessential Maine coastal experience, Giffin Log Cabin offers the perfect setting to unwind, explore, and create lasting memories.brbrPlease Note:brThis property rents Saturday–Saturday during the summer. The calendar will display available check-in/check-out days; the week in between will be grayed out.

Great Location! Expansive deck with huge yard! Well maintained path to the rocky shoreline.

Bailey Island, Maine, United States

Bed

Bath

Sleeps

$419.96

Welcome to Sherrill's Seaside Cottage!brbrPerched gracefully on a high point of the island, Sherrill's Seaside Cottage offers classic Maine charm paired with sweeping, elevated views of iconic Mackerel Cove. Whether you're sipping your morning coffee on the covered porch or unwinding on the patio at sunset, you'll be treated to a front-row seat to some of the most peaceful and picturesque scenery Bailey Island has to offer.brbrJust a short stroll down the quiet dead-end road brings you to a right-of-way path leading to Little Harbor, a wonderful spot for exploring tidepools, wading, or taking in a serene sunrise. The location alone makes this cottage a quintessential seaside retreat.brbrInside, the home exudes warmth, comfort, and timeless cottage character. The well-equipped kitchen provides everything you need to prepare family meals or fresh seafood feasts. Off the kitchen is a cozy sitting room with a small TV, perfect for relaxing after a day by the water. This room also offers access to the lower-level bathroom, which features a classic clawfoot soaking tub to help you melt into vacation mode. A washer and dryer conveniently tucked into this lounge area make longer stays even easier.brBright and welcoming, the sitting area opens to an outdoor patio with ocean views, ideal for reading, morning yoga, or evening wine. From there, step into the cottage's charming dining area, where cove views accompany every meal. A nearby cozy living room offers comfortable seating for conversations, board games, or simply enjoying the soft breeze drifting in from the water.brbrUpstairs, you'll find three inviting bedrooms and two bathrooms.brThe first bedroom, located to the upper right of the stairs, features a queen-size bed and direct ocean views. A delightful way to wake each morning.brThe second bedroom offers a spacious king-size bed and plenty of room to relax.brThe third bedroom, perfect for younger guests or solo travelers, includes a trundle bed and a charming window bench, a perfect nook for reading or daydreaming as you overlook the treetops.brThe upper level also includes a full bathroom with a stand-up shower as well as a separate half bath for added convenience.brbrWith its vintage touches, thoughtful updates, and stunning natural setting, Sherrill's Seaside Cottage is the perfect place to relish the slower, scenic charm of coastal Maine.brbrCome enjoy Sherrill's Seaside Cottage today! With views like Sherrill's… you'll be glad you booked it!brbrPlease note: Fireplace is not available for renter(s) use.

3 bedroom, 2 bathroom classic Maine cottage with ocean views into Mackerel Cove

Bailey Island, Maine, United States

Bed

Bath

Sleeps

$352.27

Welcome to Cedar Ledge Cottage! This recently updated, bright cottage features beautiful easterly views of Casco Bay, open, sunlit living spaces, comfortable bedrooms, and is located just a short walk away from Cedar Beach. You'll love the ocean breezes, shaded porch, and easy access to local restaurants and shops.brbrInside the cottage you'll find an open concept living room and eat-in kitchen with seating for four and large picture windows that fill the space with natural sunlight and sweeping ocean views. The living room opens to the master bedroom with a king bed and ocean views. Next door, there is a second bedroom with two twin beds and a shared full bathroom with a walk-in shower. From the living room, you enter the breezeway/front entrance with a washer and dryer and access to a shaded porch with table and chairs for four to relax and enjoy.brbrOutside, you'll love the sunny, open lot and friendly neighborhood, great for walking. From the cottage, you are within walking distance of Cedar Beach (0.4mi), the Bailey Island General Store (0.4mi), Fishnet Cafe (0.4mi), Mackerel Cove (0.8mi), Cook's Lobster & Ale House (1.1mi) and H2Outfitters and Salt Cod Cafe (1.3mi) just over the Cribstone Bridge. Come enjoy all Bailey Island has to offer from this lovely ocean view home!brbrDogs under 20 pounds are welcome (a non-refundable pet fee applies). More than one dog requires permission from host. If booking on VRBO click on Travelers box and check box by I am traveling with pets. brbrNote- The owners of this wonderful home are located next door and the driveway is shared. Given the proximity to neighbors, we do ask that guests respect quiet time between 10pm and 7am.brbrBed types/descriptions:brMaster with King BedbrSecond Bedroom with Two Twin BedsbrCommon Space- Full Size Sofa BedbrbrBathroom setup/description: brFull Bath with Shower OnlybrbrAir Conditioning: NobrBeach Access: NobrBeach Towels: Not includedbrDeparture Cleaning: IncludedbrCable TV: Yes, in living room brClosest Shopping Village: Brunswick, 23 min awaybrCoffee Maker: Yes, regular drip brDishwasher: NobrGrill: Gas grill available, Propane providedbrHeat Source: Forced hot air furnacebrInternet Access: Yes, Xfinity Cable Internet and WiFibrLinens & Bath Towels: Included, beds are made prior to guest arrival and towels remain in their sanitized packaging, placed on each bedbrLobster Pot: YesbrOutdoor Firepit: NobrParking: 1-2 carsbrStairs to Water: NobrTrash Removal: Included, picked up weekly (for multi-week stays) or upon departurebrTV: Smart TV in Living RoombrUsable Fireplaces: NobrWasher & Dryer: YesbrWater Frontage: NobrWater Source: Well water with filtration system, bottled drinking water recommended

Recently updated cottage featuring beautiful easterly views of Casco Bay

Bailey Island, Maine, United States

Bed

Bath

Sleeps

$235.28

Welcome to Whitesail's Cottage!brbrTucked near the very end of picturesque Bailey Island, Whitesail's Cottage is the perfect cozy coastal escape. This charming retreat offers classic Maine character, beautiful water views, and the soothing rhythm of the Atlantic tides just outside your door. From the spacious deck, you can watch the lobstermen come and go from the cove, listen to the waves, and soak in the peaceful island atmosphere. A short stroll brings you to the rocky shoreline, ideal for exploring tidepools, beachcombing, or simply admiring the ever-changing seascape.brbrStep inside and you'll find a quaint, well-equipped kitchen ready for preparing everything from a quick breakfast to a full Maine seafood feast. Continue on into the welcoming living area, where sliding glass doors frame the water view and lead out onto the large deck, your outdoor haven for relaxing with a book, enjoying a meal, or taking in the salty breeze.brbrJust off the living area is the cottage's cozy bedroom, complete with a queen bed and a twin bed, offering flexibility for couples, friends, or small families. A charming enclosed porch area adds extra space to unwind and enjoy quiet moments. For your convenience, a washer and dryer are located in the cellar, accessed via the outdoor bulkhead.brbrSimple, sweet, and full of coastal charm, Whitesail's Cottage offers an affordable and unforgettable island getaway. Come enjoy the gentle tides, ocean breezes, and the timeless beauty of Bailey Island.brbrPlease note this property rents Saturday–Saturday in summer. The calendar will show available check-in/check-out days, and the week in between will be grayed out. Fireplace is not available for renter(s) use.

Lovely deck to watch the boats come and go, and incredible sunsets!

Bailey Island, Maine, United States

Bed

Bath

3

Sleeps

$654.97

New Listing!brbrWelcome to Oceanside Oasis — Your Coastal Escape on Beautiful Bailey IslandbrbrSlow down to the rhythm of the tides at Oceanside, a serene island retreat where breathtaking water views, fresh ocean air, and classic Maine charm come together for the perfect getaway. Ideally located just steps from local restaurants, a neighborhood store, scenic walking trails, and some of Bailey Island’s most beloved beaches, this home puts the very best of the coast right at your doorstep.brbrWake up to unforgettable sunrises over Casco Bay from two east-facing porches—perfect for sipping your morning coffee or watching lobster boats pass by. Spend your days wandering down to Cedar Beach for a swim, combing Pebbly Beach for sea glass, or enjoying dinner and drinks just a short stroll away.brbrInside, the home is bright, modern, and thoughtfully designed for comfort in every season. On the main level, you'll find a beautifully furnished, well-appointed kitchen, living, and dining area, all with gorgeous easterly views of Casco Bay. Upstairs are two comfortable, spacious bedrooms the primary offering a king bed and the other a queen bed. Between the bedrooms you'll find access to an elevated porch, as well as a shared full bathroom with a tile shower and separate soaking tub, the perfect place to relax after a long day of exploring all Harpswell has to offer. For quiet moments of relaxation, unwind in the ground level bedroom and living area, offering a king bed, powder room, and sitting area with TV. On cooler days, guests can enjoy radiant heat, a cozy fireplace in the living room, and the peace of mind of an automatic generator.brbrStep outside to beautifully maintained grounds, including a peaceful courtyard, a private front yard with a firepit and stone patio, and mature coastal landscaping that enhances the sense of privacy and calm. Guests also enjoy a right of way to Casco Bay, adding a touch of adventure to your stay.brbrOceanside isn’t just a place to stay—it’s an experience. Come discover the beauty, ease, and magic of island life on Bailey Island.brbrSorry, pets are prohibited. Thank you for your consideration and understanding.brbrAir Conditioning: NobrBeach/Water Access: Shared path to sandy/rocky/pebbly shoreline just a few steps away at the end of Oceanside RdbrBeach Towels: Not includedbrDeparture Cleaning: IncludedbrCable TV: No Cable, Smart TV in Living Room and Lower Level BedroombrClosest Shopping Village: Brunswick, 20min awaybrCoffee Maker: Nespresso CoffeemakerbrDishwasher: YesbrGrill: Gas Grill available, Propane providedbrHeat Source: Radiant Heat Oil Burning FurnacebrInternet Access: Yes, Fidium Fiber Optics and WiFibrLinens & Bath Towels: Included, beds are made prior to guest arrival and towels remain in their sanitized packaging, placed on each bedbrLobster Pot: YesbrOutdoor Firepit: YesbrParking: 2-3 carsbrStairs to Water: No stairs, path to waterbrTrash Removal: Included, picked up weekly (for multi-week stays) or upon departurebrTV: Smart TV in Living Room and Lower Level BedroombrUsable Fireplaces: Yes, Gas Fireplace in main floor living roombrWasher & Dryer: Yes, located in main floor full bathroombrWater Frontage: Water View with Shared Water Access via PathbrWater Source: Well water with filtration/softener system, bottled drinking water recommended

Oceanside Oasis, New Listing, Steps from the Ocean, Perfect Bailey Isl Escape

Bailey Island, Maine, United States

Bed

Bath

Sleeps

$312.32

Welcome to Garrison Cove!brbrIf you're dreaming of a peaceful and romantic coastal escape, Garrison Cove is the perfect retreat. Nestled in the serene West Shore neighborhood of Bailey Island, this charming cottage offers an intimate setting designed exclusively for two. With breathtaking sunsets over Harpswell Sound, quiet coastal surroundings, and cozy indoor comforts, Garrison Cove provides everything you need for a rejuvenating couple's getaway.brThough modest in size, this cottage is thoughtfully arranged to maximize comfort and charm. Step inside and you'll find yourself in a warm and welcoming space ideal for slow mornings, relaxing afternoons, and unhurried evenings by the sea. The sunroom, bathed in natural light, invites you to unwind with a cup of coffee, a good book, or simply the panoramic beauty of the water beyond. On pleasant days, the patio area offers a peaceful spot to enjoy ocean breezes, share a meal, or sip a glass of wine at sunset.brThe cottage features a full kitchen equipped with clean, updated appliances, providing everything you need to create your favorite dishes, especially those famous Maine lobster feasts. Whether you choose to dine inside, outside, or down on the shore, the setting is always serene.brThe cozy bedroom includes a queen-size bed, perfect for restful nights after a day of exploring. Just steps away is the full bathroom, complete with a convenient stand-up shower and all the essentials. Thoughtful amenities such as wireless internet and a Smart TV ensure comfort and modern convenience throughout your stay.brFor those who love the water, Garrison Cove offers something extra special: access to a pebbly beach, perfect for walking, wading, collecting sea glass, or simply taking in the quiet beauty of Harpswell Sound. Whether you're watching the tide roll in, spotting seabirds, or enjoying the colors of the setting sun, this little slice of the coast is sure to steal your heart.brGarrison Cove is a peaceful haven designed for couples who want to slow down, reconnect, and savor the magic of Maine's coast.

Sweet 1 bedroom cottage tucked along Harpswell Sound' shore, quiet location and wonderful views

Bailey Island, Maine, United States

Bed

Bath

Sleeps

$431.69

Welcome to Edgecliff!brbrPerched at the very edge of the crashing surf in beautiful Little Harbor, Edgecliff is a bright and spacious second-floor garage apartment offering guests a true taste of Maine's rugged coastline. With sweeping ocean views, soothing sea breezes, and a peaceful atmosphere, this sunny retreat is the ideal escape for couples seeking relaxation, romance, and the beauty of the open water.brbrAs you arrive, follow the exterior staircase up to the expansive private deck, where you'll immediately be greeted by the sound of waves rolling in below. Complete with comfortable lounge chairs, this generous outdoor space is perfect for morning coffee, afternoon reading, or sunset conversations while taking in the spectacular coastal scenery. Large windows and sliding glass doors line the front of the apartment, inviting in abundant natural light and framing the ocean just steps away.brInside, Edgecliff features a bright open concept living space thoughtfully designed for comfort. The living area includes a cozy sofa, equipped with a pull-out bed for any additional sleeping needs, as well as a TV for winding down after a day of exploring the island. A small dining table provides the perfect spot for meals, games, or planning your next adventure. The kitchen is efficiently arranged, offering everything you need for preparing simple meals during your stay.brbrA full bathroom is situated just off the living space, providing convenience and privacy. Toward the back of the apartment, you'll find the bedroom, which features a queen-size bed and an additional TV which makes for a restful, comfortable space to end each day.brbrEdgecliff's location is truly exceptional. Enjoy a scenic stroll to one of Maine's most iconic coastal landmarks, the “Giant Stairs”, where dramatic rock formations and sweeping Atlantic views create an unforgettable experience. Prefer sandy shores A short drive brings you to the beloved beach at Lands End, perfect for swimming, exploring, or simply enjoying the ocean air.brbrWhether you're celebrating a special occasion or simply craving a quiet escape by the sea, Edgecliff offers the perfect setting for a romantic getaway for two. With its unbeatable location, peaceful ambiance, and inviting living space, this coastal retreat promises to become a favorite Maine memory.

Apartment

This spacious 2nd floor garage apartment offers phenomenal open ocean views!

Bailey Island, Maine, United States

Bed

Bath

Sleeps

$434.91

This Maine summer cottage on Bailey Island sits on a high bluff overlooking the ocean. First bought by great, great grandparents on their honeymoon trip, it has been in the family for over 125 years. The bedrooms are beautiful, the dining room is large and sunny, and the view is spectacular! Enjoy sitting on the covered porch with a cup of coffee in the morning, watching the sun rise “out of the ocean”, lobster men hauling their traps and sailboats passing by. Settle in for a lazy afternoon with a good book or explore the island, collect shells on the beaches, rent a kayak and skim along the waves or go fishing. The college town of Brunswick, just a 25 minute drive away, is great for antiquing and to see summer stock theater. Visit the Maine Maritime Museum in nearby Bath, go outlet shopping in Freeport or travel just beyond to browse Portland's historic waterfront. Dine at the island's restaurants or cook lobster at home. Fun for couples and great for families!

1890 Summer Cottage on an Ocean Bluff

Bailey Island, Maine, United States

Bed

Bath

Sleeps

$487.72

Perched overlooking picturesque Mackerel Cove and The Back Beach, rests The Beach Rose, a beautiful coastal cottage with stunning westerly ocean views. You'll love spending your mornings on the front porch, watching the lobstermen set out for their day on the water. Your days will be filled with trips to Mackerel Cove to soak up the sun, comb the beach for treasures, and take a refreshing dip in the ocean, coming back to the house for a tasty lunch or exploring one of the island's restaurants to enjoy delicious, fresh seafood, and at the end of the day, you will surely find yourself back on the porch to watch the sunset over the ocean, painting the sky with gorgeous hues of pink, orange, and purple. brbrInside The Beach Rose, you will find a wonderfully updated home with modern, coastal décor and comfortable furnishings throughout. The first floor offers a well-equipped kitchen, dining area, and a comfortable living room with a wonderful bay window overlooking the ocean. The living room opens to a back deck offering outdoor seating and a grill. On the first floor, you will also find a washer & dryer and a full bathroom. Upstairs, there are three spacious bedrooms with lush, inviting bedding, and a shared full bathroom with a walk-in shower. You'll love the creature comforts throughout the home, making for a wonderfully relaxing vacation by the sea. brbrLocated in the heart of Bailey Island, you will enjoy being just a short walk/drive away from all the islands have to offer, including Sundrenched (1.2mi away), Cook's Lobster & Ale House (1.3mi), Fishnet Café (0.4mi), Bailey Island General Store (0.4mi), Land's End Gift Shop (1mi), Salt Cod Café (1.5mi), H2Outfitters (1.5mi), Island Candy Company (2mi), and several great local beaches. You will also enjoy being just 20 minutes from all the restaurants, shops, and pubs of Brunswick. brbrBook your Maine vacation at The Beach Rose today and make memories this summer to last a lifetime. brbrPets are considered at The Beach Rose and a non-refundable pet fee does apply. Please reach out to MaineStay Vacations for more information. brbrBed types/descriptions:brSecond Floor: Master Bedroom with Queen Bed, Ocean Views, and Door to Shared Bathroom brSecond Bedroom with Queen Bed and Ocean Views brThird Bedroom with Twin Trundle Bed (2 Twins) and a Double Bed brbrBathroom setup/description: brFirst Floor- Full Bathroom with Shower/Tub Combo brSecond Floor- Full Bathroom with Walk-In ShowerbrbrAir Conditioning: NobrBeach Access: Yes, public access to Mackerel Cove 5min walk awaybrBeach Towels: Not includedbrDeparture Cleaning: IncludedbrCable TV: No, Smart TV with streaming services onlybrClosest Shopping Village: Brunswick, 22 min awaybrCoffee Maker: Yes, KeurigbrDishwasher: YesbrGrill: Gas grill available, Propane providedbrHeat Source: Rinnai Heater in Kitchen/Dining Area, Propane Fireplace in Living Room, and Electric Fireplaces/space heaters available upstairsbrInternet Access: Yes, Xfinity Cable Internet and WiFibrLinens & Bath Towels: Included, beds are made prior to guest arrival and towels remain in their sanitized packaging, placed on each bedbrLobster Pot: YesbrOutdoor Firepit: NobrParking: 2 carsbrStairs to Water: NobrTrash Removal: Included, picked up weekly (for multi-week stays) or upon departurebrTV: Smart TV in Living RoombrUsable Fireplaces: Yes, Propane Fireplace located in Living RoombrWasher & Dryer: YesbrWater Frontage: No, water viewbrWater Source: Well water with filtration system, bottled drinking water recommended

The Beach Rose - 3BR, 2BA home perched overlooking picturesque Mackerel Cove

Bailey Island, Maine, United States

Bed

Bath

Sleeps

$304.86

The perfect seaside retreat, The Bailey Island Condo is conveniently located on Bailey Island overlooking scenic Mackerel Cove, just a short walk away from public beaches, local stores, seafood restaurants, and all the beautiful sights and walking trails Harpswell has to offer including the historic Cribstone Bridge, the Giant Stairs, and Land's End. You'll love the stunning views from your deck, easy water access via the public beach and field at the head of the cove, and the ability to buy lobsters right off the wharf for the perfect Maine meal on your vacation!brbrInside, you will find an open concept living, kitchen, and dining area with a fully stocked kitchen, flat-screen TV, and electric heat for chilly nights. Upstairs, you'll find a full bathroom and ocean view bedroom with stunning views of the cove and a sliding door opening to a balcony, the perfect place to enjoy your morning coffee or tea as you watch the sun rise over the peninsula.brbrCome to Bailey Island this summer and fall (to see the gorgeous foliage) and enjoy this wonderful condo right in the heart of the island and close to all this seaside community has to offer! Spend all day basking in the sun, go for a swim in the cove, launch your boat or kayak in the cove from the beach and explore the coast, take a walk to the local stores and restaurants, or take a drive to explore the surrounding coastal areas (Brunswick (15 min), Freeport (30 min), Portland (1hr), or Boothbay (1hr)) offering a variety of restaurants, stores, and activities. The opportunities for adventure are endless and I'm sure this comfortable condo will keep you coming back year after year!brbrGuests please note the following:brPets - Sorry, this property does not allow pets.brLaundry - The condo does not have a washer and dryer, but there are several laundromats in Brunswick, just 15min away.brSmoking - Smoking is prohibited.brQuiet Hours - We kindly ask guests to observe the quiet hours between 10pm and 8am. Thank you!brbrBed types/descriptions:brSecond Floor- Ocean View with Queen BedbrExtra Sleeping Area - First Floor - Living Room Sofa Opens to sleep 2 additional guestsbrbrBathroom setup/description: brSecond Floor- Full Bath with Shower/Tub CombobrbrAir Conditioning: Yes, condo has window AC unit located in the window at the top of the stairsbrBeach Access: NobrBeach Towels: Not includedbrDeparture Cleaning: IncludedbrCable TV: No (local HD channels through antenna hookup)brClosest Shopping Village: Brunswick, 23 min awaybrCoffee Maker: Yes, regular dripbrDishwasher: YesbrGrill: Electric grillbrHeat Source: ElectricbrInternet Access: Yes, Xfinity internet + WiFibrLinens & Bath Towels: Included, beds are made prior to guest arrival and towels remain in their sanitized packaging, placed on each bedbrLobster Pot: YesbrOutdoor Firepit: NobrParking: 1-2 carsbrStairs to Water: NobrTrash Removal: Trash bags in dumpster by parking lot; recyclables in grey bin on deck upon departurebrTV: Smart TV in living room & bedroom brUsable Fireplaces: NobrWasher & Dryer: NobrWater Frontage: YesbrWater Source: Well water, bottled water recommended

Condo

The perfect seaside retreat overlooking scenic Mackerel Cove on Bailey Island

Bailey Island, Maine, United States

Bed

Bath

4

Sleeps

$502.84

Welcome to the Blue House!brTucked away on one of Bailey Island's premier locations overlooking Casco Bay, this gorgeous 3-bedroom, 2-bath gem has everything you'll need for a dream vacation.brBest of all, right outside, there's access to a private beach shared with only a few other houses. Swimming, tide pooling, fishing off the rocks, relaxing by the water, watching boats on the open Atlantic, you can do it all! Have a kayak Bring it, and you can launch right from the beach!br Inside the house, on the main level, there's a welcoming eat-in kitchen, a sunroom/breakfast nook with access to a large deck, and a spacious living area that includes a dining table. All have clear views of the water. Also on the main level is the primary bedroom with a queen size bed, and a half bathroom with a washer and dryer.br Upstairs, there are two more bedrooms, both with queen size beds. Also on this level, there's a large, bright living area with a Roku TV and fabulous views, another sunroom overlooking the ocean, and a full-size bathroom with a tub/shower combo. br The house is close to multiple restaurants, fishing spots, and hiking trails. Wander down the street to Mackerel Cove, pick up some fresh lobsters, listen to the waves while you make dinner, and enjoy a feast on the deck overlooking the water. It's the perfect spot for a coastal Maine vacation! Book today!brThere is an exterior, outward-facing security camera located above the back deck. It allows video monitoring of the yard and driveway, but it does not monitor or record audio. brbr Please note: fireplaces are not for tenants' use.br Also: if you're traveling with friends or extended family, the Blue House can be rented with the Yellow Cottage located next door.

Gorgeous ocean views with private beach access.

Bailey Island, Maine, United States

Bed

Bath

Sleeps

$440.31

Perched overlooking Merriconeag Sound rests this charming, beautifully furnished 2BR, 1.5 BA Bailey Island cottage. Perfectly located in the West Shore neighborhood, you'll love being within walking distance of all the islands have to offer including Cook's Lobster & Ale House, Sundrenched, Fishnet Cafe, Bailey Island General Store, and just a short drive away from other great local eats. Spend your days lounging on the sunlit deck watching the lobster boats pass by or go on a nearby adventure. Just make sure you make it back in time for the glorious sunsets over the sound.brbrInside the cottage are two bedrooms, each with a queen size bed, a full bathroom with a shower on the first floor, with a half bathroom on the lower level, fully stocked kitchen, and a living room area with a sofa, two chairs and a flat screen TV. For additional comfort, the cottage offers heat pumps with A/C for hot summer days. Outside there is an elevated deck with a picnic table, umbrella, and two adirondack chairs, a yard area, and stairs to access the waterfront.brbrExperience Maine, the way life should be, at Sunset Cottage and it will surely beckon you back for years to come!brbrPlease note- The stairs to access the waterfront are very steep. For easy kayak access, we would recommend launching from Garrison Cove, just down the road.brbrDogs are welcome at Sunset Cottage (a non-refundable pet fee applies). More than one dog requires permission from the host.brbrBed types/descriptions:brLower Level:brFirst Bedroom with a Queen BedbrSecond Bedroom with a Queen BedbrbrBathroom setup/description: brFirst Floor/Upper Level- Full Bathroom with ShowerbrLower Level- Half BathroombrbrAir Conditioning: Yes, via heat pumps located on first floor and in both lower level bedroomsbrBeach/Water Access: Direct, on property via private stairs, rocky/pebbly shorelinebrBeach Towels: Not includedbrDeparture Cleaning: IncludedbrCable TV: Cable TV in Living RoombrClosest Shopping Village: Brunswick, 22min awaybrCoffee Maker: Yes, automatic dripbrDishwasher: YesbrGrill: Gas Grill available, Propane providedbrHeat Source: Heat PumpsbrInternet Access: Yes, Xfinity Cable Internet and WiFibrLinens & Bath Towels: Included, beds are made prior to guest arrival and towels remain in their sanitized packaging, placed on each bedbrLobster Pot: YesbrOutdoor Firepit: NobrParking: 2 carsbrStairs to Water: YesbrTrash Removal: Included, picked up weekly (for multi-week stays) or upon departurebrTV: Smart TV in Living RoombrUsable Fireplaces: NobrWasher & Dryer: YesbrWater Frontage: Direct ocean frontagebrWater Source: Well water with filtration/softener system, bottled drinking water recommended

Sunset Cottage - Capture Breathtaking Sunsets from this Beautiful Home

Bailey Island, Maine, United States

Bed

Bath

Sleeps

$1379.94

brJAQUISH LANEbrPerched on a stretch of rocky Maine coast, Jaquish Lane is a fully renovated oceanfront compound with stunning views of the sea from nearly every room. The property is well off the main road, and offers total privacy. Jaquish Lane consists of two separate structures (Jaquish House and #14) connected by an open grassy lawn.brbrJAQUISH HOUSE is a large, luxurious family home with a huge open plan living area with sweeping ocean views. The master suite has breathtaking views from the king sized bed - as well as the jacuzzi soaking tub.brbr“NUMBER 14” is a gem-like efficiency honeymoon cottage for two from the early 1900’s - when there was little else on the island.brbrEnjoy naps on the porch or walk to nearby beaches, restaurants and shops. Explore tidepools along the water’s edge or take advantage of the world class striper fishing from the rocks . Eat lobster freshly pulled from the sea by local lobstermen. Go sailing to nearby Eagle Island or kayak the miles of peaceful Harpswell coastline. Curl up in front of the fireplace with a book and a glass of wine. brbrWhatever you choose to do, it all comes back to the view. Crashing waves or perfect calm – the sea is a constant and ever changing presence at both Jaquish House and Number 14. Sit back and watch the ocean change with the weather. Hour by hour. Minute by minute. Always different. Always beautiful.brbrJaquish Lane is a place to gather, surrounded by friends and family. A place for sharing meals and stories and remembering how wonderful it feels to truly let yourself slow down.brbrBoth JAQUISH HOUSE and NUMBER 14 were completely renovated in early 2015. The chefs kitchen features all new appliances as well as high efficiency washer and dryer. Bedrooms all have brand new mattresses and are furnished with luxury bedding and linens. JAQUISH HOUSE features one King sized Master suite with en suite bathroom featuring an oceanfront jacuzzi soaking tub. One Queen bedroom with ocean views, one Queen bedroom with 48 television and blu ray player, and one bunk room with 4 twin beds. Free wifi - high speed internet throughout. NUMBER 14 has one Queen bed, an ensuite bathroom with clawfoot tub and tiled shower, and a kitchenette with sink, stovetop, microwave and fridge.brbrNUMBER 14 is available from May 1st to November 1st.br*br*br*brEVENTSbrJaquish Lane is perfectly set up to host small weddings, family reunions, or other special gatherings, and can be rented with the property next door - The Gills (vrbo 318909) which sleeps an additional 6 and The Red House (vrbo 1063510) which sleeps 4. All three cottages are a part of THE GILLS GROUP.brbrDepending on the size and type of gathering there are additional event fees / insurance requirements for ALL events. Please inquire to learn more about these fees and .br*br*br*brAVAILABILITYbr If the summer dates you are looking for aren't available at Jaquish Lane, please check out my other two properties on Bailey Island that make up THE GILLS GROUP.brbrVRBO Property # 318909 (The Gills) which sleeps 6 and VRBO Property # 1063519 (The Red House) which sleeps 4. The Gills Group cottages can be rented together to accommodate parties of all sizes.br*br*brPETSbrPets are welcome at Jaquish House and will incur a fee of $60 per night per pet. This is non-negotiable. Everyone says, My pet would never damage anything, but sadly, experience has proven that's not always the case.br*br*br*brBAILEY ISLANDbr25 minutes from Brunswick and Bowdoin College. 40 minutes from Freeport and L.L.Bean. 55 minutes from Portland. Bailey Island is the perfect place to unplug, recharge, and reconnect with family and friends.br*br*br*brTHE OWNERbrMy name is Carter Smith and I am the owner of THE GILLS GROUP (The Red House, Jaquish Lane and The Gills). I was born on Bailey Island and after traveling the world I know that this little island is special. As both a photographer and filmmaker, I travel quite a bit and I've furnished the houses with things I've collected from around the world (and around Maine). These are not just rental propertiesto me . These are houses I've designed and furnished with love and attention to detail - places where I spend time with family and friends whenever I get the chance. Places that I love sharing.br*br*br*brWHEN USING ONLINE BOOKING - YOUR RESERVATION WILL NOT BE CONSIDERED CONFIRMED UNTIL YOU COMMUNICATE WITH THE PROPERTY MANAGER

PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room

Bailey Island, Maine, United States

Bed

Bath

Sleeps

$491.72