Home Vacation Rentals By Owner In Greenport, NY

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Exceptional(85)

$914.0

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Cottage

Cottage on Beach front Estate with Dockage .Walk to Village

Greenport, New York, United States

Charming 2-bedroom cottage located on a family-owned waterfront estate that was converted from a circa 1920s chicken coop. This retreat has inspiring views of Shelter Island and is only steps away from the peaceful waters of the Peconic bay. Described by as 'one of the last saltwater farms,' the estate is not only picturesque, but is also an exemplary model of a traditional working farm. Gentle breezes off the bay keep the house naturally cool, so air conditioning is rarely, if ever, needed. Lots of room indoors and out makes the cottage both kid- and pet-friendly. The deck and sprawling lawn make for a great place to entertain friends and family, or the perfect spot to lie back, relax, and relish the view. Stroll along the estate's expansive private beach or have a picnic overlooking the water. The beautiful tree-filled grounds complete the pristine view of the bay and Shelter Island, making the estate an artist’s paradise for all seasons. The cottage is quiet and secluded, yet within easy walking distance to Greenport Village, offering the best of both worlds. brbrWith a strong nautical history, Greenport is a water-lover’s paradise and the perfect destination for sailing, boating, fishing, swimming, kayaking, and canoeing. Mitchell Park Marina is just a short walk from the estate and provides transient slips by the day or week. Please call in advance for reservations to secure your spot. brbrWhile downtown in the village of Greenport, explore the local boutiques and stores. Take advantage of the history-rich Railroad, Stirling–Ireland House, and East End Seaport museums. Ride the antique carousel, or take a tour of the harbor on The Glory, an electric launch. Sample the local bounty from land and sea in a variety of restaurants offering casual fare to award-winning dining. Tour the over 42 vineyards located here on the North Fork. Discover the art galleries featuring local and international artists who represent the contemporary to the classic. So much tucked into one square mile and all conveniently within walking distance! brbrGreenport's proximity to Manhattan, Connecticut, and the South Shore means you don’t have to go far to get away. Enjoy a casual drive from the city, or let the LIRR or Hampton Jitney carry you here stress free. Either way there is something for everyone, so come and experience what makes Greenport charming and unique. For more information about Greenport and all it has to offer, brbrThe estate also offers additional accommodations that when combined can be perfect for family gatherings. Please visit listing #173361--“The Gate House” or 234929 the main housebrbrbrKeywords: Cottage
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Bath 1

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Sleep 4

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Exceptional(2)

$1710.67

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Private Vacation Home

The Village Villa – Renovated 6-Bedroom Home in the Heart of Greenport Village

Greenport, New York, United States

Welcome to the Village Villa—a newly renovated, spacious 6-bedroom home nestled right in the heart of Greenport Village. With two full kitchens and two bathrooms, this property is ideal for families or groups seeking comfort, convenience, and charm.brbrLocated just steps from beloved local restaurants, the grocery store, and a wine and liquor store. A short walk to Front Street’s vibrant selection of coffee shops, breakfast cafés, award-winning restaurants, boutiques, bars, the Greenport Marina, and Mitchell Park—you’ll be perfectly positioned to enjoy everything the Village has to offer.brbrSleeps up to 13 guestsbrbrOutdoor SpacesbrStep outside to a private backyard patio strung with twinkling lights—an ideal setting for morning coffee, al fresco dinners, or relaxing under the stars. Enjoy meals at the umbrella-shaded dining table in a peaceful, tucked-away setting.brbrThe property also features:br- A long, wide driveway with space for multiple vehiclesbr- A spacious, grassy side yard—great for lawn games or relaxing in the sunshinebr- A shaded front porch—perfect for sipping coffee and watching the village come to lifebrbrBedroom LayoutbrMain Floorbr- 1 King Bedroombr- 1 Full (Double) Bedroombr- 1 Twin (Single) Bedroombr- 1 Sleeper Sofa (Double)brbrUpstairsbr- 1 King Bedroombr- 2 Full (Double) BedroomsbrbrGuest AccessbrGuests can enter through the front door to access the upstairs or the side door at the top of the driveway to access the main floor. The home is equipped with a keyless electronic lock on the front door. You’ll receive an access code before your arrival for a smooth, contactless check-in.brbrOther things to notebr- The garage is not accessible to guests for cars but can be made available for bike storage upon request.br- There is no interior stair case that links the upstairs and downstairs apartments. Both have private outdoor entrances. br- 5-minute drive or 20-minute walk to 5th Street Beach (no parking pass required).br- 5-minute drive or 10-minute walk to the Greenport Train Station, Hampton Jitney stop, and Shelter Island Ferry.brbrWhether you're planning a weekend getaway, a wine country adventure, or a family vacation, the Village Villa offers the ideal home base in one of Long Island’s most charming and walkable towns.
Bed 6

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Bath 2

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Sleep 13

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Exceptional(2)

$959.68

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Private Vacation Home

The Village Villa Top Floor–Renovated 3-Bed in the Heart of Greenport Village

Greenport, New York, United States

Welcome to the Village Villa—a newly renovated, spacious 3-bedroom home nestled right in the heart of Greenport Village.brbrLocated just steps from beloved local restaurants, the grocery store, and a wine and liquor stores. A short walk to Front Street’s vibrant selection of coffee shops, breakfast cafés, award-winning restaurants, boutiques, bars, the Greenport Marina, and Mitchell Park—you’ll be perfectly positioned to enjoy everything the Village has to offer.brbrOutdoor SpacesbrStep outside to a shaded front porch—perfect for sipping coffee and watching the village come to life. The property also features a long, wide driveway with space for multiple vehiclesbrbrBedroom Layoutbr- 1 King Bedroombr- 2 Full (Double) BedroomsbrbrGuest AccessbrGuests can enter through the front door. The home is equipped with a keyless electronic lock on the front door. You’ll receive an access code before your arrival for a smooth, contactless check-in.brbrbrOther things to notebr- The top and bottom floor share no common spaces and have completely separate private entrances.br- The backyard is reserved for 1st floor guests onlybr- The garage is not accessible to guests for vehicles but can be used for bike storage upon requestbr- 5-minute drive or 20-minute walk to 5th Street Beach (no parking pass required).br- 5-minute drive or 10-minute walk to the Greenport Train Station, Hampton Jitney stop, and Shelter Island Ferry.brbrWhether you're planning a weekend getaway, a wine country adventure, or a family vacation, the Village Villa Top Floor offers the ideal home base in one of Long Island’s most charming and walkable towns.
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Bath 1

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Sleep 6

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Exceptional(3)

$1030.4

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Private Vacation Home

The Village Villa 1st Floor—Renovated 3-bed in the heart of Greenport Village.

Greenport, New York, United States

Welcome to the Village Villa 1st Floor—a newly renovated, spacious 3-bedroom home nestled right in the heart of Greenport Village.brbrLocated just steps from beloved local restaurants, and the grocery store. A short walk to Front Street’s vibrant selection of coffee shops, breakfast cafés, award-winning restaurants, boutiques, bars, the Greenport Marina, and Mitchell Park—you’ll be perfectly positioned to enjoy everything the Village has to offer.brbrOutdoor SpacesbrStep outside to a private backyard patio strung with twinkling lights—an ideal setting for morning coffee, al fresco dinners, or relaxing under the stars. Enjoy meals at the umbrella-shaded dining table in a peaceful, tucked-away setting.brbrThe property also features:br- A long, wide driveway with space for multiple vehiclesbr- A spacious, grassy side yard—great for lawn games or relaxing in the sunshinebrbrBedroom Layoutbr- 1 King Bedroombr- 1 Full (Double) Bedroombr- 1 Twin (Single) Bedroombr- 1 Sleeper Sofa (Double)brbrGuest AccessbrGuests can enter through the side door, towards the middle of the driveway. The home is equipped with a keyless electronic lock on the front door. You’ll receive an access code before your arrival for a smooth, contactless check-brin.brbrOther things to notebr- The 1st floor and top floor units have no shared spaces and have completely private separate entrances.br- The backyard is reserved for 1st floor guests only.br- The garage is not accessible to guests for cars but can be made available for bike storage upon request.br- 5-minute drive or 20-minute walk to 5th Street Beach (no parking pass required).br- 5-minute drive or 10-minute walk to the Greenport Train Station, Hampton Jitney stop, and Shelter Island Ferry.brbrWhether you're planning a weekend getaway, a wine country adventure, or a family vacation, the Village Villa 1st Floor offers the ideal home base in one of Long Island’s most charming and walkable towns.
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Bath 1

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Sleep 7

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$728.85

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Cottage

'The Gate House'on Beach front Estate with Dockage. Walk to Village .

Greenport, New York, United States

Located on a family-owned waterfront estate, The Gate House, a cozy 2-story, 2-bedroom cottage, is only steps away from the tranquil waters of the Peconic bay. 'one of the last saltwater farms,' the estate is not only picturesque, but is also an exemplary model of a traditional working farm.brbrLots of natural light makes the house wonderfully cheerful, and gentle breezes from the water keep the house naturally cool. The intimate slate patio and sprawling lawn make for a great place to entertain friends and family. Stroll along the estate's expansive private beach or have a picnic overlooking the water. The beautiful tree-filled grounds complete the pristine view of the bay and Shelter Island, making the estate an artist’s paradise for all seasons. With room to roam and nature to explore, the property is both kid- and pet-friendly. The Gate House is peaceful and secluded, yet within easy walking distance to downtown Greenport Village, offering the best of both worlds. brbrWith a strong nautical history, Greenport is a water-lover’s paradise and the perfect destination for sailing, boating, fishing, swimming, kayaking, birdwatching brbrWhile downtown in the village of Greenport, explore the local boutiques and stores. Take advantage of the history-rich Railroad, Stirling-Ireland House, and East End Seaport museums. Ride the antique carousel, or take a tour of the harbor on The Glory, an electric launch. Sample the local bounty from land and sea in a variety of restaurants offering casual fare to award-winning dining. Tour the over 42 vineyards located here on the North Fork. Discover the art galleries featuring local and international artists who represent the contemporary to the classic. So much tucked into one square mile, and all conveniently within walking distance! brbrGreenport, a short distance from Manhattan, Connecticut, and the Hamptons means you don’t have to go far to get away. Enjoy a casual drive from the city, or let the LIRR or Hampton Jitney carry you here stress free. Either way there is something for everyone, so come and experience what makes Greenport charming and unique. For additional information about Greenport and all it has to offer, please visit the official village website supported by the Greenport BID. Make sure to enter Greenport Village in your search. brbrCherry Lane Farm also offers additional accommodations that when combined can be perfect for family gatherings. Please visit listing #167288--“Cottage on Waterfront Estate” or main house listing 234929brbrbrKeywords: The Gate House
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Bath 1

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Sleep 4

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Exceptional(1)

$567.87

/ Nightly
Cottage

Greenport Waterfront Cottage w/Private Beach

Greenport, New York, United States

Located in the historic and centuries-old town of Greenport Village with its quiet streets, serious dining broptions and plentiful natural beauty, it offers quick access to town restaurants, shopping, North Fork vineyards and golf courses including nearby Island’s End. This charming waterfront cottage is located on bracres of property at the end of a private drive. The Cottage boasts waterfront views, water’s edge deck and private beach plus expansive lawn with basketball and tennis courts for those who prefer activities away from the water. Feel free to bring your bikes or kayak. If you are looking for a low-key alternative brto the Hamptons, this is it!brThis spotless and fully stocked home offers all linens and every kitchen item you will need. Also included brare coffee maker, toaster, full size fridge, microwave and stove. A full-size washer and brdryer and outdoor grill are available for your use. Sleeping options include private king bedroom and king pullout.brThis property is truly special and must be seen to appreciate! brGreenport with its mile square waterfront has existed since the 1600’s and is equally charming and brconvenient. Walkability with varied homes/interesting architecture, harbors, shoppes and bars make brthis the perfect place for those who prefer a more casual feel than the traffic filled Hamptons. brHydrangeas rather than privacy hedges can be seen, along with picket fences and farmhouse or saltbox brstyle homes. Groceries, pharmacy items, liquor stores, bookstore and train, ferry or bus services to and brfrom NYC and Shelter Island allow for easy living and travel.brTime spent in Greenport could include an early happy hour in town or a trip to one of the dozen brvineyards within a short distance, visits to Little Creek Oyster Farm and Market, Crazy Beans breakfast or brlunch, fantastic pizza and other specialties from 1943 Pizza Bar, a more upscale dinner at Noah’s, brwaterfront dining at Port where you can view the ferries coming and going…. often with live music, ice brcream from one of three in town, Margaritas and Mexican food from Lucharito’s, Greek food at Hellenic brRestaurant (best lemonade!), a burger or chicken sandwich from Andy’s where you are likely to catch bryour favorite sport on the TV’s, a visit to the local lavender farm or a quick drive or bike ride into Orient br(last town before dropping into the water at Long Island’s end). A visit to Clark’s Garden and Home, a brunique garden and home shop and lots of boutique shopping! A 10- minute ride on the ferry to Shelter brIsland affords you more beauty and dining options plus you can make a 2-mile bike ride or drive to Mashomack Preserve for those who would enjoy hiking on trails allowing for 2-10 miles with 2300 brstunning acres edged in white by 11 miles of coastline and which accounts for 1/3 of that island.
Bed 2

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Bath 1

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Sleep 4

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Exceptional(43)

$1633.77

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Private Vacation Home

Beach/Waterfront 7.2 ac Estate with Dockage -40 ft

Greenport, New York, United States

Same location I have two 2 cottages that sleep 4 each . See VRBO search bar [Where To] with the Listing ID 173361 and the Listing ID 167288.brbrThe centerpiece of this family owned waterfront estate, “The Main House” is a neo-victorian 5-bedroom, 3-bathroom sauna room and outdoorshower charmer that comfortably sleeps 8 - 10 people. brbrThe panoramic porch with stunning water views, the spacious living room, the large dining room and kitchen and expansive outdoor patio and deck make this vacation paradise one of a kind. brbrWhether you’re planning a family reunion or looking to escape to the natural wilderness of the North Fork, this house has it all. Stroll along the estate’s private beach or have picnic overlooking the water. brbrThe beautiful tree filled grounds are complete with pristine views of the bay and Shelter Island. With room to roam and nature to explore, the property is both kid and pet friendly. The house is fully furnished and linens are provided. brbrThe house is quiet and secluded, yet within easy walking distance to Greenport Village, offering the best of both worlds. brbrWith a strong nautical history, Greenport is a water-lover’s paradise and the perfect destination for sailing, boating, fishing, swimming, kayaking, and canoeing. Mitchell Park Marina is just a short walk from the estate and provides transient slips by the day or week. brbrPlease call in advance for reservations to secure your spot. brbrWhile downtown in the village of Greenport, explore the local boutiques and stores. Take advantage of the history-rich Railroad, Stirling–Ireland House, and East End Seaport museums. brbrRide the antique carousel, or take a tour of the harbor on The Glory, an electric launch. Sample the local bounty from land and sea in a variety of restaurants offering casual fare to award-winning dining. brbrTour the over 42 vineyards located here on the North Fork. Discover the art galleries featuring local and international artists who represent the contemporary to the classic. So much tucked into one square mile and all conveniently within walking distance! brbrGreenport's proximity to Manhattan, Connecticut, and the South Shore means you don’t have to go far to get away. Enjoy a casual drive from the city, or let the LIRR or Hampton Jitney carry you here stress free. brbrEither way there is something for everyone, so come and experience what makes Greenport charming and unique. For more information about Greenport and all it has to offer, please visit the official village website supported by the Greenport BID. Make sure to enter Greenport Village in your search. brbrThe estate also offers additional accommodations that when combined can be perfect for family gatherings. Please visit listing #173361--and--167288brbrbrKeywords: House
Bed 5

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Bath 2

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Sleep 10

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Exceptional(10)

$842.63

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Private Vacation Home

Family and Friends in Historic Greenport

Greenport, New York, United States

Our house is an historic Dutch colonial, both cozy and spacious, with warm wood trim and wood floors throughout. The 20 x 20ft. Great Room, a perfect gathering space for family and friends is complete with a baby grand piano, cable TV, children's toys and books, classic novels and wood burning fireplace has sliding glass doors opening to a large deck with dining table and gas grill. Fully equipped kitchen opens to formal dining area with bay windows. Upstairs, there is a full bath with tub and shower and 3 bedrooms with central AC. One has a queen cherry wood sleigh bed and glass door to a sun deck with table and chairs for morning coffee or evening cocktails. The second bedroom upstairs has a queen bed and the third has two twin beds. Downstairs bedroom suite has two rooms, one with a queen bed, the other a twin, full pull out couch, window AC and gas fireplace. The tall privet hedge and the green of the lawn and garden combine to create a private setting. Maximum number of guests as per Greenport code: 6brbrOur house is in the historic village of Greenport. Close to all transportation, you can walk to the bus, train and ferry terminal.brbrBeaches everywhere! Less than a mile from the house. the pebbled Long Island Sound beaches and sandy bay beaches are perfect for swimming. brbrWine tastings and performances are held at the nearby wineries year round. Fall is a special time: apple and pumpkin picking, grapes are gathered, harvest festivities and farm stands full of local produce. Springtime abounds with local eggs, flowers and the historic Strawberry Festival. brKeywords: Beach, Village, Greenport
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Exceptional(20)

$1247.23

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Private Vacation Home

Gorgeous 5 bdrm home with beautiful bay views in the heart of Greenport Village

Greenport, New York, United States

Enchanted home with beautiful bay views. This house has it all. Modern updates with old-world charm. Gorgeous chefs kitchen, hardwood floors throughout, stone and marble baths. Located in the center of Greenport, Walk to town. Lovely renovations throughout. The Primary bedroom has views of the water, a rare offering in the Village of brGreenport with a fully fenced in backyard.brbrThis 1870’s home has been fully renovated with custom amenities. The Interior is nautical themed with Restoration Hardware furnishings including Belgian linen, leather couches. The custom gourmet kitchen is picture perfect. A gorgeous blend of wood and tiles that creates the perfect place to gather and to entertain. There are 2 sinks, 1 Farmer sink in the large custom built wood island. Subzero refrigerator, Wolf beverage Draw refrigerator, Sub Zero Wine refrigerator and european gas top stove. The perfect place for the chef in you. brYou will find 2 Flat screen SMART TVs with Cable, Apple TV capability. There are speakers throughout the house to play music with the Sonos blue tooth system. There is Wifi throughout the housebrbrThe front room opens up to a large wrap around deck. A perfect spot to have your coffee or glass of wine and people watch. brbrThe sliding glass door off of the kitchen opens onto a deck perfect for outdoor dining and entertaining. There is a gas grill located outside..brbrThe home is bright with sunshine and hard wood floors. Easy to maintain for beachside living. brbrThe primary bedroom has gorgeous views of the bay. French doors open up to the on the balcony where you can sit and enjoy your coffee or wine while watching boats go by. Beautifully tiled updated bathroom with tiled shower. Fine linens and comforters throughout.brbrUpstairs Guest rooms has king size bed with a full bathroom with beautifully tiled showers. There is a sleigh tub for bathing smaller ones as well. brbrThe downstairs bedroom has a queen size bed. There is a full bathroom located alongside the bedroom with custom black and white tiles to give it the vintage yet modern feel.
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Sleep 10

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Exceptional(5)

$611.79

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Private Vacation Home

Charming historic house on Sterling Harbor, water views, 5-min walk to village

Greenport, New York, United States

Tucked away on Sterling Harbor in the Historic District on Greenport's most desired street is this lovely, 3-bedroom, 1780s “vernacular” house. Meticulous attention has been paid to renovations and modern additions that preserve its architectural character, accentuated by eclectic art, furniture, and artifacts from the owner's travels, A mini split-system A/C has recently been installed for your comfort.brbrThe 1st floor offers an open flow to spacious living areas — a library-foyer with working fireplace, large dining room, and a fully-equipped cook’s kitchen with Bosch/GE/Wolf appliances. The light-filled sun room opens to a deck designed for dining and entertainment, with a flowering pergola, water views, and salt breezes. The original porch has been preserved, perfect for relaxing, reading, and watching boats and passers-by.brbrOn the 1st floor: the main bedroom (queen bed) with a working fireplace and full bathroom (shower/tub). On the 2nd floor: a large bedroom with queen bed and cross ventilation; and a charming guest room with skylight for a single person. The two bedrooms have water views and share a bathroom. brbrA patio by the kitchen, with flowering arbor, water views, and Weber grill, offers additional outdoor dining possibilities. The back yard consists of a large lawn, mature trees and gardens, perfect for family games (croquet, badminton). There is a fire pit for cooler evenings. An outdoor shower awaits one's return from a day at the beach. brbrEnjoy dining al fresco with freshly caught fish from Southold Fish Market, sweet corn from Latham and Sep's Farms, greens from Sang Lee and Deep Roots Farms. Indulge in bivalves at Little Creek Oyster and artisanal beers at Greenport Harbor Brewery, both steps away on Carpenter Street; and wines from Kontokosta Winery on the Main Road, 5 minutes by foot, bike, or car. brbrA North Fork food-and-wine destination, the village abounds with attractions: the North Fork Arts Center, Burton’s Bookstore, Mitchell Park and the Carousel, boating/fishing tours, restaurants, cafés, bakeries, markets and shops, and a farmers' market on Fridays. Public beaches are nearby -- 67 Steps & Inlet Pond on Long Island Sound; 4th St and 5th St beaches, Gull Pond & Sandy Beach, all on Peconic Bay.brbrTransportation: The Long Island Railroad (LIRR), Hampton Jitney, & Long Island Expressway (LIE) all serve Greenport. North Ferry connects the village to Shelter Island and the South Ferry to the Hamptons and Montauk on the South Fork. The Cross Sound Ferry at Orient Pt, 8 miles away, plies the seas to and from New England.brbrKeywords: House
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Bath 2

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Sleep 5

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