Vacation Rentals By Owner In Southport, ME

$616.63

Stunning oceanfront cottage w/ private deck and Atlantic views

Southport, Maine, United States

Marvel at breathtaking oceanfront views of Cape Harbor, Cape Island, and the Atlantic Ocean at this stunningly situated Southport home. This property sits at the end of Gray Road (which is shared with only a handful of other homes), ensuring that your stay will be quiet and serene. Spend your afternoons upstairs on the private deck overlooking the water, reading and relaxing downstairs with a wall of windows to frame the view, and entertaining friends and loved ones in the open kitchen and living area.brbrWhat's nearby: brThis oceanfront home sits on the edge of Cape Harbor, six miles south of bustling Boothbay Harbor. When you're in town, you can sample tasty lobster rolls from Shannon's Unshelled and stroll across the longest wooden footbridge in the United States. Back at the house, when you're not walking to the local library, you'll be just over two miles from a delicious lunch at Oliver's on Cozy Harbor Wharf and three miles south of Hendricks Head Lighthouse.brbrThings to know:brFree WiFibrFull kitchenbrOne of the listed twin beds is a trundlebrThe owner sometimes uses the apartment over the garage but does not interact with guests

3

Bed

2

Bath

6

Sleeps

$1156.19

/ Nightly

Private Vacation Home

Secluded Dog-Friendly Getaway w/ Free WiFi, Private Washer/Dryer, Furnished Deck

Southport, Maine, United States

Tucked away in a private setting and surrounded by two acres of Maine forest, this charming, two-story vacation rental is the perfect home-away-from-home for your next getaway to Southport Island. Bright, pristine, and newly-built, this four-bedroom home features vaulted ceilings, comfortable furnishings, and more than a few nods to the great state of Maine with its decor and artwork. The open floor plan includes a well-equipped, island kitchen with stainless steel appliances, a large dining table with seating for eight, and a cozy living area with a Netflix-ready flatscreen TV. Outside, enjoy the sights and sounds of the woods from the furnished deck where you can socialize or fire up the grill and dine in the open air. And when it's time to call it a night, you'll find four comfortable bedrooms here including one king suite, two rooms with queen-size beds, and a kids' room with two twin bunks.brbrWhat's nearby:brThis home is within walking distance of Cozy Harbor and only a mile from Hendricks Head Lighthouse and the adjacent beach area offering terrific views and opportunities to swim in the cool waters and catch tiny crabs in the seaweed. Just a few miles northeast, check out bustling Boothbay Harbor with its many attractions and water activities. Grab a bite to eat from Robinson's Wharf offering terrific seafood, an oyster bar, and wonderful views of the cove. And if you need to stock up on essentials during your stay, the eclectic Southport General Store is less than a half-mile north of this home.brbrThings to know:brFree high-speed WiFibrUp to two family dogs (20 lbs. max.) are welcomebrBooster seat, Pack-N-Play, and baby gates are providedbrIncludes a selection of yard gamesbrA 4x4 is recommended in winter

4

Bed

3

Bath

8

Sleeps

$440.46

/ Nightly

Cottage

Cedarbush Cabin - Waterfront Cottage - walk to Robinson's Wharf!

Southport, Maine, United States

Mid-Century Modern Charm on the Waterfront!brbrDiscover the charm of coastal Maine at Cedarbush Cabin, a classic mid-century modern waterfront cottage with stunning views and relaxed vibes. Enjoy your morning coffee or evening cocktail from the deck as boats glide by, or head down to the dock and float for a closer look at the bay.brbrThis single-level cabin features two bedrooms and two full baths, a well-equipped kitchen, a cozy living room with a fireplace, and a dining area with seating for up to eight—perfect for gathering after a day of seaside adventures.

2

Bed

1

Bath

4

Sleeps

$1014.17

/ Nightly

Private Vacation Home

Beachfront Delight with detached guesthouse, private beach access, Dog-friendly

Southport, Maine, United States

Nestled on the Sheepscot River, this house and detached guest home boast a stunning waterfront location! A private beach makes it easy to enjoy tide pools and sunsets. Enjoy water views from nearly every room. Gather on the riverside deck to share alfresco meals or admire breathtaking sunset views over the water. The desirable location is just a short walk away from the Hendricks Head Lighthouse and Preserve.brbrA wood-burning fireplace creates inviting allure in the main house's living area. Relax on down-filled sofas and cast your favorite apps. On quiet afternoons, select a book from the well-stocked shelves. Whip up delicious dishes in the kitchen, appointed with an array of helpful gadgets. You'll find two tables in the dining area.brbrThe primary bedroom holds an L-shaped desk for a convenient workspace.brbrThe guesthouse has large windows that provide excellent views of the river in the living area. Handy highlights of the kitchenette include a mini-fridge, a two-burner electric stove, and an instant kettle. Sip coffee at the small table. There is a sleeping area and a bathroom with a walk-in shower.brbrKick back with crisp drinks on the guesthouse deck. Follow the stone pathway to the water's edge.brbrTHINGS TO KNOWbrAccess to the front door is via three exterior steps and an unlevel stone pathway through the yard. brThis property does not have air-conditioning.

2

Bed

2

Bath

8

Sleeps

$476.61

/ Nightly

Private Vacation Home

Waterfront Retreat on Southport Island - Pet-Friendly, Sleeps 6

Southport, Maine, United States

Welcome to your coastal escape! This 3-bedroom, 1.5-bath waterfront home is tucked away on Southport Island, a hidden gem in Maine’s Boothbay region. Known for its scenic beauty and maritime heritage, Southport offers a peaceful, authentic coastal experience while keeping you close to the shops, dining, and activities of nearby Boothbay Harbor.brbrThe HomebrbrPerfect for families, small groups, or couples traveling together, this home comfortably sleeps six guests. Inside, you’ll find:brbrThree cozy bedrooms and 1.5 bathroomsbrbrA fully equipped kitchen for preparing fresh local seafood dinners or simple family mealsbrbrAn open dining room/living area with space to relax, play games, or curl up with a book.brbrStep outside and the real magic begins. The property sits right on the water, offering a front-row seat to the tides and Maine’s ever-changing coastal views. Start your morning with coffee overlooking the shoreline, enjoy picnics by the water, or spend evenings stargazing in the quiet salt air.brbrThe LocationbrbrSouthport Island is the perfect blend of serenity and adventure. Connected to Boothbay Harbor by a historic swing bridge, the island offers easy access to local attractions while keeping you tucked away in a more tranquil setting. brbrGuests can enjoy:brbrBoating, kayaking, and paddle boarding right from the island.brbrNature walks and hikes through pine forests and along the rocky coast.brbrLocal beaches and landings, perfect for a summer swim or simply soaking up the view.brbrFresh lobster and seafood from local shacks and markets.brbrA quick drive to Boothbay Harbor, where you’ll find boat tours, shopping, galleries, and family-friendly attractions like the Coastal Maine Botanical Gardens.brbrPet-Friendly StaybrbrWe know vacations are better with the whole family, which is why your pets are welcome here. There’s plenty of space for them to enjoy the fresh air right alongside you.brbrWhether you’re seeking outdoor adventure, a quiet coastal retreat, or a little of both, this Southport Island waterfront home is the perfect place to make lasting Maine memories.brHouse Rules & Helpful Infobrbr-Fireplace: Please DO NOT use the fireplace!brbr-Trash & Recycling: Please remove all trash, including any food left in the fridge, and place bagged trash in the outdoor bins.brbr-Recycling does not need to be sorted, except for bottles and cans that are refundable in Maine. These can be set aside—feel free to return them to a local redemption center, or housekeeping will collect them.brbr-No Smoking: Smoking is not permitted anywhere inside or outside on the property.brbr-No Fireworks: Fireworks are strictly prohibited on the premises.brbr-Damage Policy: Accidents happen—please report any damage promptly so we can address it quickly. The Damage Waiver covers unintentional damage to the property and its contents up to $1500, provided damages are reported to Ohana Vacations before check-out. (Airbnb reservations excluded)brbr-Starter Pack: Ohana provides a starter supply of essentials (toilet paper, paper towels, soap, etc.). Guests are responsible for replenishing the following items as needed.brbrThese items ARE NOT included...brbr-Spices & condimentsbrbr-Mosquito/tick repellentbrbr-Personal hygiene itemsbrbr-Sunscreenbrbr-Beach towelsbrbrGrill Use: If a grill is available, please do not move it and keep it 5–10 feet from the house at all times. Kindly clean the grill after each use.brbrIf propane runs out, please contact Ohana customer service for a replacement.brbrPrivate Wells & Septic Systems: Some of our homes use private wells and septic systems. brbr-Please: Flush only toilet paper—no wipes, feminine products, or other items.brbr-Avoid driving on the lawn, as pipes run underground.brbr-Be mindful of water usage.

Bed

Bath

Sleeps

$450.25

/ Nightly

Cottage

Cottage at Island Point; Charming Coastal Retreat

Southport, Maine, United States

The Cottage at Island Point – Southport Island, Maine. Hosted by Of Sea and Pine, Maine Vacation RentalsbrbrCome experience the charm of coastal island living at this serene Southport cottage. Nestled in the peaceful Newagen community, The Cottage at Island Point feels like stepping into an Edward Hopper painting—where life slows down, sea breezes fill the air, and the soothing sound of buoy bells will be your evening soundtrack.brbrThis inviting retreat sleeps six, with ocean glimpses from every bedroom and multiple outdoor spaces to enjoy Maine’s natural beauty. The outdoor dining area is perfect for a quintessential lobster bake under the stars. This is truly “The Way Life Should Be.”brbrPlease note: This is a fairly remote location. A vehicle is needed to access the home and surrounding areas; Uber does not operate in the area. There are no dogs allowed at this property. brbr Key Features:brMultiple Outdoor Spaces, including a firepit, balconies and a furnished dining areabrPeaceful and welcoming community atmosphere. Easy access to Newagen Seaside Inn, Southport Yacht Club, Hendrick’s Head Beach and downtown Boothbay Harbor brbr Home Layout: br• Primary Bedroom: King bed with peeks of the water br• Second Bedroom: Two twin bedsbr• Third Bedroom: Two twin bedsbrBathrooms:br• 2 Full Bathrooms (both located upstairs)bro One with a stand-up showerbro One with a bathtubbr*Please note, there is no air conditioning at this property br br♿ Accessibility: All bedrooms and bathrooms are located on the second floor, accessible only via a steep and narrow staircase. This property may not be suitable for guests with mobility limitations.brbr Parking: Free off-street parking is available for 2–3 vehicles.brbrNeighborhood Note: This cottage is located in a friendly, close-knit neighborhood with other cottages nearby. You may hear and see neighbors in their yards, children playing, or dogs barking. Guests are kindly asked to respect quiet hours between 9:00 PM and 7:00 AM.brbr Location & Local Charm: brLocated at the southern tip of Southport Island in the charming village of Newagen, this cozy cottage offers the perfect blend of tranquility and proximity. Though you may feel like you’re at the edge of the world, you're just a short drive over the iconic swinging bridge to the vibrant harbor town of Boothbay, known for its restaurants, boutique shops, art galleries, boating excursions, and ice cream parlors.brbr Things to Do Nearby: brStroll to Town Landing Pier with your morning coffee and take in the views of Cuckolds Light Station and Cape IslandbrbrMake reservations for the Newagen Inn’s lobster bakebrbrSpend a quiet afternoon at the Southport LibrarybrbrTour the Newagen Alpaca FarmbrbrPack a picnic from the Southport General Store and head to Hendricks Head Beach, where another iconic Maine lighthouse awaitsbrbrEnjoy dinner with a view at Robinson’s Wharf or Cozy’s DocksidebrbrVisit the Coastal Maine Botanical Gardens and see the magical giant trollsbrbrPlay tennis or pickleball with a day pass at the nearby YMCAbrbrA complete guidebook will be provided at booking, filled with recommendations for day trips, dining, and local activities. Need help planning Just ask—we’re happy to help you find your happy place in Maine.

3

Bed

2

Bath

6

Sleeps

$201.65

/ Nightly

Cottage

Charming Two-Bedroom Ocean-View Cottage in Quiet Southport

Southport, Maine, United States

Located on Southport Island, this cottage is a dream for travelers looking to enjoy the slower pace of life. Sip your morning coffee on the wraparound deck with a view of the ocean and enjoy a book or puzzle at night next to the wood-burning fireplace. Our cottage offers a cozy retreat tucked away in the forest; you'll love being able to unwind at our beloved family vacation home. Keep an eye out for summer fireflies flitting about at twilight!brbrWhen you're ready to wander afield, the famed Boothbay Harbor is a short 10-minute drive away with plenty of boutique shops, restaurants, local saltwater taffy, boat tours, and more! You'll also want to check out the nearby Coastal Maine Botanical Gardens and Maine State Aquarium for some local daytime activities.

2

Bed

1

Bath

4

Sleeps

$531.88

/ Nightly

Private Vacation Home

Cedar Cove: a tranquil retreat on the water just minutes from Boothbay Harbor

Southport, Maine, United States

Cedar Cove was completed in 2023 and designed for tranquility: find yourself surrounded by woods and water, in a beautiful section of Southport Island, not far from beaches or marinas. Wood floors and siding allows the home to blend in, in its location, and you'll find all the necessary modern amenities (new washer, dryer, stove, fridge, work space and smart TVs) inside. brbrThe home is just minutes from multiple restaurants on Southport, and is just 10 minutes from Boothbay Harbor, a lively town with great restaurants, shops, activities, live music and much more.

Bed

Bath

Sleeps

$499.38

/ Nightly

Cabin

Oceanview Cabin Retreat in Southport

Southport, Maine, United States

The sound of the waves will greet you even before you can lay your eyes on the ocean. Sunset views from the front porch are some of the best in the region, and the ocean waves a comforting sound. Sprucerock Cabin faces west with a broad view of the mouth of the Sheepscot River Bay. Surrounded by pine trees with its own rocky shorefront, this is a perfect place to unwind.brbrInside you will find the rustic comfort of a old-school Maine cabin with some with a beautiful vaulted ceilings. There are spectacular water views from the living room and primary bedroom. A gas fireplace adds to the ambiance and makes for cozy nights. Bringing you back in time, enjoy a sink in every bedroom, a showcase to the time. The kitchen is well-equipped, welcoming, and perfect for preparing meals at home. Escape to a tranquil getaway at this classic Maine cabin with all one-floor living. There are two full bathrooms (one with a walk-in shower and the other with a claw-foot tub/shower).brbrWhen you can tear yourself away, it`s a 6-minute walk over to the Newagen Seaside Inn for a lovely dinner out or to enjoy music in the pub. The town landing is a great place to fish or go for a swim. Walk the 1/2 mile to the Southport Memorial Library where you can feel the history and warmth of this island community. Join in the children`s story hour or take in one the speaking engagements. Learn about Rachael Carson or Margaret Hamilton, both famous summer residents. A short walk away you will also find Cape Newagen Alpaca Farm and gift shop where you can learn all about these beautiful animals and maybe even get a kiss from an Alpaca! With so much to do, it will be hard to venture off the island, but when you do, downtown Boothbay Harbor is only a 7 mile drive away.brbrGuests have access to the entire cabin. There is a Keurig coffee maker at this home. This property has a few neighboring cottages and you can walk along the road to get to several rocky beach areas. brbrWe will meet you upon arrival for a quick tour and to answer any questions you have. We are available 24/7 during your stay.brbrIMPORTANT:brInstead of placing a security deposit hold on your card, we include a small, non-refundable $25 damage waiver in the reservation total—so your funds remain available throughout your trip. This Waiver covers damages up to $300.br• Quiet hours are 9:00 PM – 9:00 AM. Please respect our neighbors at all times.br• Maximum occupancy is as shown on the listing. Additional guests are subject to $25/person/night and may result in cancellation if excessive.br• A mandatory, non-refundable damage waiver is included in your reservation total in place of a security deposit. Guests remain responsible for damage exceeding coverage or resulting from negligence or rule violations.br• Pets are not allowed without prior approal and non-refundable pet rent.br• No smoking or vaping anywhere on the property (indoors or outdoors).br• Open flames (fireplaces, fire pits, etc.) require prior written approval.br• No parties, events, or large gatherings without written approval.br• Waterfront/dock use (if applicable) is at your own risk and may require an additional waiver.

3

Bed

2

Bath

6

Sleeps

$831.13

/ Nightly

Private Vacation Home

Stunning Renovated Waterfront Home with Private Deepwater Dock; Windows Galore!

Southport, Maine, United States

On the water with expansive views and a private deepwater dock on the property for your boat. This location cannot be beat. This year round home is located on Southport Island, a short five-minute drive from the hustle and bustle of Boothbay Harbor. It is perched on the edge of Townsend Gut with water views from every room. You could easily spend the entire day watching the boats travel past from the porch while listening to the seagulls sing. Robinson’s Wharf (the island’s most popular restaurant) is a short walk away. The house underwent a full renovation in early 2018 which included all new furniture/ decorations and is ready for visitors! If you need more space a seasonal cottage adjacent to this property is also available for rent on VRBO #1380743.brThe main level has an open floor plan with living, dining and kitchen that look out onto Townsend Gut – the views are stunning. Three sliding doors lead to the porch that is perfect for relaxing, watching the world go by and happy hour. This level also contains a large master bedroom with a queen bed and a full wall of windows overlooking Decker’s Cove. The master bathroom has ample closet space, double sinks and walk in shower. The main floor powder room includes a stackable washer/dryer for those lucky enough for longer stays.brThe upper level views rival those of downstairs with 3 bedrooms and 1 bathroom with a tub shower. Two bedrooms have queen beds and the third bedroom has a pair of twin beds. brThe property is stunning with new professional landscaping and ample space for lawn games or lounging under the large trees while watching the tides rise and fall. There is a private deepwater dock right in the yard if you want to bring your boat. brSouthport Island is only a 5 minute drive from downtown Boothbay Harbor – just over the Townsend Gut Swing Bridge. Southport Island is close enough to Boothbay but also has its own restaurants and sites. Robinson’s Wharf, Cozy's Dockside and Newagen Inn are highly recommended restaurants on the island. Hendricks Head Beach is located on the west side of the island. Sailing, boating and kayaking are spectacular activities in and around the island. If you want to venture off the island, the Boothbay Harbor Region has extensive nature trails, lake swimming (Knickerbocker Lake), golfing, an aquarium and one of the best Botanical Gardens in the country. brbrbrbr**you can also rent the 1 bedroom cottage on the property if you need more space. VRBO listing #1380743. Contact Kim for more info**

4

Bed

2

Bath

8

Sleeps

$536.81

/ Nightly

Private Vacation Home

PINE CLIFF DWELLER | 2 Bed, 2 Bath

Southport, Maine, United States

Pine Cliff Dweller: Classic Coastal Comfort and Panoramic ViewsbrbrPerched on a cliff overlooking the entrance to Boothbay Harbor and the islands of the Atlantic, Pine Cliff Dweller is a treasured family home ready for your next memorable Maine vacation. This cozy, traditional cottage serves as a popular home base for both adventurers and those seeking a quiet retreat, offering a warm and inviting atmosphere that feels like a true home away from home.brbrCharming FeaturesbrPanoramic Ocean Vistas: Watch the world go by from the dining room, which features three walls of windows overlooking the ocean, your private dock, and surrounding islands.brClassic Maine Ambiance: Enjoy the cozy feel of this non-minimalist retreat, complete with a working, wood-burning fieldstone fireplace that serves as the heart of the home.brMaster Suite with A/C: The second-floor master bedroom features a king bed, panoramic views, and air conditioning to ensure comfort on warm summer nights.brPrivate Dock and Float: Witness the activity of the harbor firsthand, from elegant yachts to hardworking lobster boats. You may even spot porpoises, migratory shorebirds, or the occasional whale. Love fresh seafood You can connect with local lobstermen for dockside service right on your private dock!brInviting Living Spaces: The open layout is filled with natural light thanks to large windows and sliding doors, making it easy for guests to gather in the family room or living area.brPerfect for Groups: With a bedroom and full bathroom on each floor, this home is ideal for two couples or small families. For larger gatherings, the neighboring cottage, Piffi Biff, can be rented in conjunction for a multi-family getaway.brbrThe Details:brbrMinimum Stay: Weekly (Saturday-Saturday) during June, July, and August; 4-night minimum in the Fall. Stay for a week or longer during the Fall to receive a better value on your booking! BEDROOMS: (1) King (Master with A/C), (1) Queen. BATHROOMS: (2) Full bathrooms, both featuring tub/shower combinations. DOGS PERMITTED No, pets are not allowed at this property. LINENS & TOWELS INCLUDED Yes, linens and towels are included in your reservation.brbrExplore the RegionbrSouthport Island Exploration: Discover the quiet charm of the island, including the Southport General Store, Hendrick's Head Beach, and the scenic views along the shore.brIconic Sightseeing: From the cottage, you have a front-row seat to views of Burnt Island and Squirrel Island.brBoothbay Harbor Entrance: Enjoy being at the gateway of the region's most famous harbor, just a short drive from downtown shops and restaurants.brbrBook your classic Maine retreat at Pine Cliff Dweller today!brbrCOTTAGE CONNECTION Vacation Rentals. Privately Owned. Professionally Managed. Trusted since 1993. Cottage Connection was one of the first vacation rental companies in the Midcoast region of Maine. Since being founded by Jeff and Audrey Miller in 1993, Cottage Connection has been trusted by homeowners and vacationers alike to connect each family with the perfect vacation cottage.

Bed

Bath

Sleeps

$1417.0

/ Nightly

Cottage

Ocean front cottage on a drive-on island in Boothbay Harbor, Maine

Southport, Maine, United States

Exquisitely maintained 5 bedroom/2 bathroom cottage right on the ocean. Family owned since 1891. Step back in time into a cottage furnished with antiques and historical items from Maine. Incredible views of the ocean on all sides. Spacious bedrooms, clawfoot tub, indoor and outside shower, huge eat in kitchen stocked with cookware of all kinds, a beautiful wrap around upper deck with lounge chairs for views of the sunrise over the ocean, a sunlit cozy reading nook stocked with books, steps from a private beach cove and dock to swim, at the private end of a beautiful drive-on island with a tennis and pickleball court, and an historic casino building. All this is just a short drive into Boothbay Harbor for dining & nightlife, boat tours, shopping and fun. This cottage has been a treasure for our family and I am finally opening it up for some responsible and respectful folks.

Bed

Bath

Sleeps

$286.13

/ Nightly

Private Vacation Home

Updated Cottage on Water’s Edge with Deepwater Boat Dock!

Southport, Maine, United States

On the water with deepwater dock for your boat - this location cannot be beat. This cottage is located on Southport Island, a short five-minute drive from the hustle and bustle of Boothbay Harbor. It is perched on the edge of Townsend Gut with water views from every room. You could easily spend the entire day watching the swing bridge open and close for the boats traveling past. Robinson’s Wharf (the island’s most popular restaurant) is a short walk away. The cottage underwent a full renovation in early 2018 and is ready for visitors!brThe cottage has an open floor plan with the kitchen opening into the living room. The large bedroom has 1 queen bed and an attached bathroom. This quaint brcottage has all you need for a quiet vacation on the water. brThe property is stunning with new professional landscaping and ample space for lawn games or lounging under the large trees while watching the tides rise and fall. There is a dock right on property for those who wish to bring their boat. On those busy summer days you'll hear the noise of the cars crossing the swing bridge.brSouthport Island is only a 5 minute drive from downtown Boothbay Harbor – just over the Townsend Gut Swing Bridge. Southport Island is close enough to Boothbay but also has its own restaurants and sites to see. Robinson’s Wharf, Cozy's Dockside and Newagen Inn are highly recommended restaurants on the island. Hendricks Head Beach is located on the west side of the island. Sailing, boating and kayaking are spectacular activities in and around the island. If you want to venture off the island, the Boothbay Harbor Region has extensive nature trails, lake swimming (Knicker Bocker Lake), golfing, an aquarium and one of the best Botanical Gardens in the country. brbr**you can also rent the 4 bedroom house on the property if you need more space. VRBO listing # 1379766. Contact Kim for more info**

Bed

Bath

Sleeps

$587.51

/ Nightly

Private Vacation Home

Decker Cove Southport Paradise with Central Air Conditioning

Southport, Maine, United States

Brand new construction in 2019. 3 bed, 3 bath home. Partial view of Decker Cove from all bedrooms, walking distance to Robinson's Wharf Restaurant. Central Air Conditioning, Radiant Heat, Gas Fireplace in Great Room, Open Concept Living Room, Dining Room, Kitchen with gas range, dishwasher, built in microwave and coffee station. The kitchen is equipped with everything you might need to cook a gourmet meal, or simply heat up leftovers from your favorite local restaurant! Enjoy the fire pit in front yard, and on the 40 foot Farmers porch overlooking the view of Decker Cove. If you are early riser, sunrise from the firepit area can't be beat! Master Bathroom has 5 foot by 4 foot walk in shower with dual shower heads and slipper soaking tub, upstairs bathroom has tub shower combination, and downstairs bathroom has 4 foot shower. Enjoy grilling on the barbecue on the end of the 12 by 20 hard top gazebo. The outdoor gazebo is screened in and has lounge furniture as well as a dining table that seats 8! On Sunday afternoons the band at Robinson's Wharf can be heard from the front porch and front yard. We have cornhole, extra large Jenga game and other lawn games for you to enjoy as well! This truly is your home away from home!

Bed

Bath

Sleeps

$190.75

/ Nightly

Cottage

Charming Plumpoint Cottage On Southport Island

Southport, Maine, United States

Enjoy the serenity of beautiful Southport Island in a classic Maine cottage with a peek at Decker's Cove. Walk to Robinson's Wharf lobster pound to enjoy dinner on the pier, an ice cream cone or, bring fresh caught fish back to the cottage to cook yourself. Drive two miles to Hendrick's Head sand beach on the island or to downtown Boothbay Harbor. Go 2 miles in another direction and you're at the Maine Botanical Gardens where you can spend the day hiking along the river through some of the Mid Coast's most breathtaking scenery.brbrPlumpoint Cottage has a fully equipped eat in kitchen, living room with cable TV and free WiFi, two bedrooms, a 3 season room with TV and a cozy game room with a collection of vintage games and puzzles.The cottage is on a quiet side street that is used as a local walking path around the cove.brbrThere is a gas grill in the backyard and a deck on the shed where you can sit and enjoy a peek at the cove. brbrThere is a 3 night minimum in the off season and 7 night minimum during July and August. I can occasionally rent for two or three nights in season when there is a space between longer rents. That is determined on a case by case basis.

Bed

Bath

Sleeps

$370.7

/ Nightly

Cottage

A Cozy Retreat on Southport Island

Southport, Maine, United States

This cute-as-a-button waterfront cottage is located on Southport Island across the swing bridge from Boothbay Harbor. `Periwinkle` sparkles with fresh coastal decor and hardwood floors throughout. The first of two bedrooms offers the option of a king-size bed or two extra-long twins. The second bedroom has one twin bed. The living room has a full-size sleeper sofa. There is one AC window unit in the living room area and fans to keep you cool.brbrGuests have access to the entire cottage and dock.brbrThe covered porch and boathouse deck provide perfect places to relax while watching the bridge open for passing boats and listening to live music on Sundays from Robinson`s Wharf across the cove. Walk there to dine in or take out from their expansive menu, and don`t forget to visit the fish market for some fresh catch.brbrHarbor Choice Laundry is 3 miles away. There is basic kitchen with small range refrigerator, microwave, drip coffee maker, toaster, and a blender.brbrPoints of interest within approximately 2-4 miles include Dogfish Head Beach and Hendrick`s Head Lighthouse, Boothbay Harbor (dining, shopping, boat tours, golf, YMCA), the Maine State Aquarium, and Coastal Maine Botanical Gardens.brbrWe will meet you upon arrival to transfer keys and give a quick tour. We are available 24/7 during your stay.brbrPets may be allowed at the property but will need prior approval from the Property Manager and will be subject to a non-refundable pet fee.brbrIMPORTANT:brInstead of placing a security deposit hold on your card, we include a small, non-refundable $25 damage waiver in the reservation total—so your funds remain available throughout your trip. This Waiver covers damages up to $300.br• Quiet hours are 9:00 PM – 9:00 AM. Please respect our neighbors at all times.br• Maximum occupancy is as shown on the listing. Additional guests are subject to $25/person/night and may result in cancellation if excessive.br• A mandatory, non-refundable damage waiver is included in your reservation total in place of a security deposit. Guests remain responsible for damage exceeding coverage or resulting from negligence or rule violations.br• Pets are not allowed at this property. Unauthorized pets may result in additional fees or cancellation. ADA Compliant Service Animals are permitted.br• No smoking or vaping anywhere on the property (indoors or outdoors).br• Open flames (fireplaces, fire pits, etc.) require prior written approval.br• No parties, events, or large gatherings without written approval.br• Waterfront/dock use (if applicable) is at your own risk and may require an additional waiver.

Bed

Bath

Sleeps

$1347.0

/ Nightly

Private Vacation Home

Miradon Ocean Estate: Expansive Ocean Views

Southport, Maine, United States

Miradon Ocean Estate affectionately known as “Ole Gusty”, is an extraordinary oceanfront retreat. Designed to showcase panoramic sunsets, the home boasts ocean views that are best enjoyed from the expansive deck. Hosted by Of Sea and Pine; Maine Vacation Rentals, Miradon is located on the enchanting island of Southport, just a stone’s throw from Boothbay Harbor. The original owner was an artist and her keen eye can be found not only in the unique décor of the home, but also in her artwork displayed throughout. Her passion for cooking and hosting inspired the open-concept kitchen, which serves as the heart of the home. Her favorite cookbooks still line the kitchen counter, many with tabs marking her preferred recipes. With over 3500 square feet of living space, including 4 bedrooms, 3 bathrooms and 6 beds, this home is truly an oasis for family and friends to gather. Sleeps 8 adults. brbr Key Features:br-Spectacular views! Enjoy ocean views throughout the home. br-The open flow of the main floor is sure to inspire conversation and laughter as you enjoy coffee in the sunroom, play games in the living room, and cook meals together in the kitchen before lingering over them in the beautiful dining room.br-Stone firepit overlooking the ocean; after dinner gather around the firepit to roast marshmallows, tell stories and star gaze. br-Multiple deck spaces perfect for morning coffee or evening relaxation br-Primary bedroom with king bed and ensuite with a soaking tub and walk in showerbr-Enchanting artist's turret, beckoning creativity and inspiration (where much of the artwork in the home was created!) br-Water views and access to the rocky beach* br-Private yard brbr*Please Note: There is no water access - not conducive to swimming- there is a public beach nearby. No dogs are allowed at this property. This is a fairly remote location, a vehicle is needed to access the home and surrounding areas; Uber does not operate in the area. brbr Home Layout: brMain level – two bedrooms each with a full-size bed. Full bathroom with a walk-in shower. brSecond Floor – primary bedroom with king bed and ensuite with soaking tub and walk in shower; second bedroom with a queen bed and ensuite with walk in shower; two twin-size daybeds on the second-floor landing. brPlease be aware, there is no air conditioning at this property. There are fans in every room & opening windows in the evening is sufficient to cool the home. brbr♿ Accessibility: There are a few steps to enter the home, once inside the main level is step free, there are two smaller bedrooms downstairs and a walk in shower. brbr Parking: Parking for up to 6 cars in the driveway brbr Location & Local Charm: brThe slower pace of island life inspires leisurely exploration. Take a walk down to the Southport Library, where you’ll find cozy reading nooks and local artwork on display. Venture a bit further to the town landing to see Margaret Hamilton’s red summer cottage (she played the Wicked Witch of the West in The Wizard of Oz) on neighboring Cape Island.brbrStop by the Southport General Store for a sandwich, then head to Hendrick’s Head Beach for a swim and views of the local lighthouse. If you’re in the mood for a more bustling coastal town, drive over the swing bridge that connects Southport to the mainland and visit the quintessential village of Boothbay Harbor. Grab a fresh cup of coffee from Red Cup, then explore the many unique shops, discovering treasures along the way.brbrLooking to get out on the water The Lazy Jack sailing tour is a favorite, and the Clam Bake at Cabbage Island is certainly a treat. End the day by dining at the Thistle Inn, but be sure to return in time to catch the sunset at “Ole Gusty” with a glass of wine — it’s truly heaven!brbr Things to Do NearbybrOther nearby attractions include the Coastal Maine Botanical Gardens, the Maine State Aquarium, the Railway Village Museum, and the Boothbay Harbor Country Club. Take a scenic drive up the coast to explore popular destinations such as Damariscotta, Camden, and Rockland. A complete guidebook will be provided with these and other area attractions.

Bed

Bath

Sleeps

$398.86

/ Nightly

Cottage

Classic Boathouse - 2BD Waterfront Cottage - Dock & Float Access

Southport, Maine, United States

Classic Waterfront Cottage on Townsend Gut - Southport!brbrPerched right at the water’s edge on scenic Townsend Gut, Classic Boathouse offers front-row views of boats passing by from the comfort of your deck. This charming single-level cottage features two bedrooms, one newly remodeled full bath, and comfortably sleeps up to six guests—perfect for a family getaway or a small group of friends.brbrInside, you'll find a newly remodeled, well-equipped kitchen, a bright water-view dining area, and a cozy living room with picture-perfect scenes right outside your window.

2

Bed

1

Bath

6

Sleeps

$3905.83

/ Nightly

Private Vacation Home

Generational Southport Property w/ Private Beach Newly Available for Rent!

Southport, Maine, United States

Get ready to enjoy amazing afternoon sun on your own private sandy beach. The westerly facing house, deck, and beach make sunsets on these 3+ secluded acres a rare treasure anywhere on the Maine coast.brbrThe property has 394 feet of water frontage without a neighbor in sight, allowing for leisure in the sand or water including fishing from the protective ledge jutting out into the ocean. Southport’s iconic General Store is a peaceful mile walk away and the bustle of Boothbay Harbor’s restaurants only 5 miles back up the road.brbrThe open concept first floor has a kitchen that opens to the deck with living room and dining room just around the gas fireplace. A window lined first floor master suite is position waterside where you can open large French doors to hear the waves and walk just 50 paces to the water. The upstairs offers two bedrooms and a shared bathroom. brbrOutdoor amenities include a detached, heated and cooled bunk house containing four beds perfect for kids or grandkids to have their own sleeping space. When not enjoying the beach, your outdoor time can be spent on the expansive deck. A generator ensures uninterrupted comfort year round.brbrWe ask you to respect the firm ten person limit. If you wish to host a celebration, ceremony, or reunion please contact us prior to booking to receive written permission so we can help accommodate your perfect experience.

Bed

Bath

Sleeps

$314.68

/ Nightly

Cottage

Oceanfront Cottage Southport 3 BR 2BA, Handicapped Accessible

Southport, Maine, United States

Snowman Cottage -- Southport Enjoy water views of Cape Harbor and the open ocean from nearly every room in this 3-bedroom/2-bath cottage! The cottage has hardwood floors with area rugs. It comes fully equipped with cable TV and VCR in the living room and a well-equipped kitchen including a lobster pot, or course, microwave and a washer/dryer. It is just a short walk to the Newagen Seaside Inn where you can enjoy the amenities that include tennis courts and a pool at no cost. You supply the linens. Sorry, no pets!brbr brbrDuring your stay, partake in the Boothbay Region’s wonderful art galleries, shopping, and the many restaurants. While here, rent a sailboat or kayak, or better yet, bring your own. Join a boat cruise, a whale-watching excursion, or go deep-sea fishing. Play golf on the region's newly redesigned 18-hole course. Hike a nature trail of which there are several, bike around the island and surrounding areas, or just relax in the serene natural setting of coastal Maine.brbr brbrWe are approximately 3 hours from Boston, 3 hours from Arcadia National Park and Bar Harbor, 1 hour from Camden/Rockland and 35 minutes from Bath/Brunswick. It is about an hour’s drive to the famous L.L. Bean store and the great outlets in Freeport if you like to shop.brbr brbrIf you like the beach, it is available at the end of Southport Island. It’s a short drive to Southport Beach, a small, but sandy public beach close by the Hendricks Head Light. There is also a small general store on the island, but a full service supermarket is available in Boothbay Harbor. brbr brbrThe interestingly named Cuckolds Lighthouse, at the entrance to Newagen Harbor, is still an active lighthouse. It is said to be named after a point of land on the Thames River in England, granted to a Londoner to sooth his anger after King John had an affair with his wife. The lighthouse has many stories. One of which is that around the lighthouse the ledges around it are called “collector ledges” as it has been the site of many boating mishaps and marine rescues. It is a beacon to generations of fishermen, and a chosen burial site for some, including our region's much beloved Leland Snowman. Although Leland never lived in this “Snowman” cottage, family members have owned it in the past, thus its name.brbrKeywords: Ocean Edge cottage, open water views from almost every room, private, quaint,This cute cottage is on a dead end road on peaceful Southport Island. It is only a few feet from the water! Wonderful views abound of the open ocean, boats in the harbor and large vessels out to sea. Located at Cape Newagen Harbor, this cottage blends old and new for a light, airy feeling. The living/dining room has spruce floors and a picture window looking out to the sea, directly at Cuckhold’s Light. Charming and spacious master bedroom on the second floor windows looking right out to see with an unobstructed view of the Cuckhold’s Light. The inviting back yard is private, nicely grassed and goes right down to the ocean with a boathouse and deck. Enjoy sitting out on the open deck with chairs and a table to watch the boats go by, or enjoy the starlit sky in Maine in the evening. Sit on the open deck facing Cuckhold’s Lighthouse to enjoy great views of the Atlantic Ocean, nearby islands, and the harbor.

3

Bed

2

Bath

6

Sleeps

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