Greenport, NY Vacation Homes from ￥43,661

Greenport Vacation Homes
New York
United States of America
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An aerial view of a harbor with boats, a ship, and a dock extending into the water.

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Our top choices for Greenport vacation homes

A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

A wicker lounge chair with a white cushion on a covered deck, surrounded by a white fence.

A modern kitchen with a washing machine, microwave, oven, and a ceiling fan.

A marina with several fishing boats docked.

1. Aqua Vista

Aqua Vista

Pipes Cove

10.0 out of 10, Exceptional, (47 reviews)

10/10

Exceptional

(47 reviews)

"Great location and nice spot."

Kerri L.

The price is ￥22,819

￥22,819

￥50,345 total

includes taxes & fees

Oct 7 - Oct 8

Aqua Vista

A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

A two-story house with a balcony, a patio with outdoor furniture, and a fenced backyard.

A compact kitchen with white cabinets, a built-in oven, a microwave, and a washing machine.

A sign welcoming visitors to the Greenport Visitors Dock with no commercial traffic.

2. The SandPiper

The SandPiper

Pipes Cove

9.6 out of 10, Exceptional, (52 reviews)

9.6/10

Exceptional

(52 reviews)

"Very wonderful location so close to the train station will come back soon"

Julian V.

The price is ￥22,819

￥22,819

￥50,345 total

includes taxes & fees

Oct 18 - Oct 19

The SandPiper

An outdoor dining area with hanging lights, palm trees, and a bar.

A modern bedroom with a four-poster bed, a television, a heater, and a brick wall.

A building with a porch, a tree, and a sign that reads "OPEN SPACE".

A staircase with steps labeled 'STAIRWAY TO HEAVEN' leading to a room with a lamp and a plant.

3. American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7

Greenport

9.4 out of 10, Exceptional, (6 reviews)

9.4/10

Exceptional

(6 reviews)

"Great place! So nice."

Paul F.

The price is ￥31,317

￥31,317

￥48,187 total

includes taxes & fees

Oct 5 - Oct 6

American Beech in Greenport - Petite King Room 7

A beach with people relaxing, a pier extending into the water, and a clear sky.

A porch with a white railing, a small blue house decoration, and a 'Gone' sign.

A dock with a sign reading "Welcome to the Greenport Visitors Dock" and "No Commercial Traffic".

A two-story house with a front porch and a pathway leading to the entrance.

4. Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

Pipes Cove

10.0 out of 10, Exceptional, (32 reviews)

10/10

Exceptional

(32 reviews)

"We had a great stay!! "

Callie E.

The price is ￥27,618

￥27,618

￥66,975 total

includes taxes & fees

Oct 1 - Oct 2

Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

A wooden pathway leading to a beach with scattered rocks and greenery.

A modern kitchen with white cabinetry, a wooden door, and a long countertop.

A cozy room with a gray sofa, wooden walls, and large windows with blinds.

A spacious living room with a gray sofa, a wooden coffee table, and a dining area with a wooden table and chairs.

5. Beach Block Hideaway

Beach Block Hideaway

Pipes Cove

10.0 out of 10, Exceptional, (12 reviews)

10/10

Exceptional

(12 reviews)

"Beautiful 2 bedroom close to town. The house is well kept we would rent here again."

Teresa C.

The price is ￥38,556

￥38,556

￥81,268 total

includes taxes & fees

Oct 4 - Oct 5

Beach Block Hideaway

A modern dining area with a wooden table, white chairs, and a chandelier.

A living room with a grey sofa, a round coffee table with magazines, a wooden side table, and a large mirror on the wall.

A bedroom with a bed, a small side table with a plant, and a window with blinds.

A living room with a sofa, a chair, a coffee table, and a ceiling fan.

6. Northfork Townhouse walk to all

Northfork Townhouse walk to all

Greenport

9.4 out of 10, Exceptional, (8 reviews)

9.4/10

Exceptional

(8 reviews)

"Great property located in a quiet neighborhood within walking distance to all in Greenport. The townhouse was clean and kitchen was well- appointed with off the street parking. Playground up the street was an added bonus with a old school merry-go-round! Would definitely stay again"

Beth R.

The price is ￥58,070

￥58,070

￥112,015 total

includes taxes & fees

Oct 20 - Oct 21

Northfork Townhouse walk to all

A living room with a fireplace, a television mounted above it, a dining area with a table and chairs, and a staircase with wooden railings.

A dining area with a wooden table, white chairs, and a vase of sunflowers.

A modern kitchen with white cabinetry, stainless steel appliances, and a herringbone-patterned backsplash.

A modern kitchen with a marble island, pendant lights, and a patterned backsplash.

7. Renovated Townhouse walk to all

Renovated Townhouse walk to all

Greenport

9.6 out of 10, Exceptional, (14 reviews)

9.6/10

Exceptional

(14 reviews)

"The place was as advertised and in great walking distance to everything in town! "

Liz H.

The price is ￥50,280

￥50,280

￥102,574 total

includes taxes & fees

Oct 26 - Oct 27

Renovated Townhouse walk to all

A wooden deck with lounge chairs and a potted plant, overlooking a beach and ocean.

A coastal property with a large house, a smaller building, and a landscaped garden.

A sunlit room with large windows overlooking a beach, featuring a wooden table and chairs, and a small round table with a chair.

A bedroom with a large bed, a ceiling fan, and a view of the ocean through large windows.

8. Beachfront Greenport Villa

Beachfront Greenport Villa

Greenport

9.8 out of 10, Exceptional, (14 reviews)

9.8/10

Exceptional

(14 reviews)

"Beautiful home, great views and host!"

Kate R.

The price is ￥97,019

￥97,019

￥169,817 total

includes taxes & fees

Oct 1 - Oct 2

Beachfront Greenport Villa

An outdoor seating area with wicker furniture, a fire feature, and glasses of red wine.

A staircase with steps labeled 'STAIRWAY TO HEAVEN' leading to a brightly lit interior space.

A greenhouse with a checkered floor, a table with a lamp, and a potted plant.

A hotel reception desk with a white counter, a wooden reception desk, and a green exit sign.

9. American Beech in Greenport - Deluxe King 6

American Beech in Greenport - Deluxe King 6

Greenport

2.0 out of 10, (1 review)

2.0/10

(1 review)

"Not as advertised. Very disappointed "

Jeffrey

The price is ￥36,038

￥36,038

￥54,299 total

includes taxes & fees

Oct 1 - Oct 2

American Beech in Greenport - Deluxe King 6

A stone pier leading to a beach with houses in the background.

A dining area with a wooden table and white chairs, a teal bookshelf with decorative items, and a window with blinds.

A cozy interior with a dining area, a seating area with a patterned rug, and a kitchen with a microwave and refrigerator.

A shelf with decorative items including starfish, wicker containers, and a sign with a password.

10. Insta-worthy Couples Retreat: Perfect for romantic getaway!

Insta-worthy Couples Retreat: Perfect for romantic getaway!

Old Lyme

9.4 out of 10, Exceptional, (61 reviews)

9.4/10

Exceptional

(61 reviews)

"A beautiful little beach cottage that was just what the doctor ordered. A great place to unwind and take in the sea air."

Emily M.

The price is ￥18,554

￥18,554

￥43,661 total

includes taxes & fees

Oct 8 - Oct 9

Insta-worthy Couples Retreat: Perfect for romantic getaway!

A kitchen with white cabinets, a central island with stools, a microwave, a stove, and a large window.

A room with a blue-striped table, white curtains, a blue sofa, and a patterned rug.

A modern bathroom with a large arched window, a white bathtub, a white chair, and a bed.

A backyard with a swimming pool, lounge chairs, and umbrellas.

11. Work and Play Special! Extended Stay Discount

Work and Play Special! Extended Stay Discount

Shelter Island

10.0 out of 10, Exceptional, (59 reviews)

10/10

Exceptional

(59 reviews)

"Beautiful property. Everything so clean and welcoming. Slept so great in the comfortable beds. Pool is awesome. Everyone especially loved the outdoor shower"

Kathleen Andrews K.

Work and Play Special! Extended Stay Discount

A living room with a fireplace, a sofa, a coffee table, and a cabinet.

A modern living room with two armchairs, a sofa, a coffee table, and a large window with curtains.

A kitchen with white cabinetry, a dining table with chairs, a hanging light fixture, and a door with a frosted glass panel.

A sunset over a calm body of water with a rocky shoreline.

12. Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

Old Saybrook

10.0 out of 10, Exceptional, (14 reviews)

10/10

Exceptional

(14 reviews)

"Very clean & comfortable home, great host & location! "

Becky W.

The price is ￥31,482

￥31,482

￥70,441 total

includes taxes & fees

Oct 4 - Oct 5

Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

A hotel room with a bed, two bedside tables with lamps, a ceiling fan, a door, and a framed abstract artwork on the wall.

A living room with a black sofa, blue armchairs, a coffee table, and a flat-screen TV.

A little outdoor space to relax and enjoy the fresh air.

A single-story house with a red door, white picket fence, and a small front porch.

13. The Bay Cottage · Rocky Neck Park, Beach & Niantic

The Bay Cottage · Rocky Neck Park, Beach & Niantic

East Lyme

9.0 out of 10, Wonderful, (7 reviews)

9.0/10

Wonderful

(7 reviews)

"This house suited our needs for a place to stay while attending a nearby family reunion. Communication and check in were great and the house is very comfortable (very nice mattresses, sheets, pillows)."

Sarah G.

The price is ￥21,092

￥21,092

￥60,787 total

includes taxes & fees

Oct 1 - Oct 2

The Bay Cottage · Rocky Neck Park, Beach & Niantic

An outdoor seating area with umbrellas and wooden furniture, overlooking a body of water.

A kitchen with a wooden chair, a cabinet with glass doors, and a wall-mounted lamp.

Escape to an extraordinary compound. Huge 4600 sq ft main house + private connecting guest house. Heated gunite pool w/ safety gates for little ones. Great outdoor patios + decks, all surrounded by 40 ft hedges, making this your private sanctuary.

A bedroom with a bed, bench, and a window with a view.

14. Huge Island Getaway Pool Hot Tub Walk To Beach

Huge Island Getaway Pool Hot Tub Walk To Beach

Menantic Creek

9.8 out of 10, Exceptional, (9 reviews)

9.8/10

Exceptional

(9 reviews)

"Property great. Beautiful home with great amenities"

Harry K.

The price is ￥93,635

￥93,635

￥176,294 total

includes taxes & fees

Oct 5 - Oct 6

Huge Island Getaway Pool Hot Tub Walk To Beach

A modern kitchen with white cabinets, a microwave, and a large TV displaying a beach scene.

A bedroom with a bed, a bedside table, a lamp, and a window with curtains.

A living room with a wooden dining table, two grey upholstered chairs, a grey sofa, and a white coffee table.

A kitchen with white cabinets, a microwave, an oven, and a dining table with a chair.

15. Adorable Cottage, 5 min walk to water & town

Adorable Cottage, 5 min walk to water & town

Westbrook Center

9.2 out of 10, Wonderful, (17 reviews)

9.2/10

Wonderful

(17 reviews)

"Very nice small place to stay by the beach and close to great coffee shop. "

Donovan V.

The price is ￥26,060

￥26,060

￥74,214 total

includes taxes & fees

Oct 1 - Oct 2

Adorable Cottage, 5 min walk to water & town

A dining area with a round table, six chairs, and a chandelier.

A modern living room with a black sofa, a grey armchair, and a black coffee table.

A modern kitchen with white cabinets, a large island with bar stools, and a view of the outdoors.

A bedroom with a large bed, two bedside tables, a nightstand, and a window with curtains.

16. Year round Jacuzzi - Blackberry Home

Year round Jacuzzi - Blackberry Home

East Hampton

9.2 out of 10, Wonderful, (7 reviews)

9.2/10

Wonderful

(7 reviews)

"We had a great time staying here. The home is well worn and there are some fixtures that should be replaced "

Suzanne R.

The price is ￥22,189

￥22,189

￥213,541 total

includes taxes & fees

Oct 4 - Oct 5

Year round Jacuzzi - Blackberry Home

A living room with a fireplace, a grey armchair, and a large window.

A modern bedroom with a bed, a ceiling fan, and built-in lighting.

A living room with a grey sectional sofa, a small coffee table, and a grey armchair. There are two windows providing a view of a residential area.

A modern house with a patio area featuring outdoor furniture.

17. Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

Waterford

10.0 out of 10, Exceptional, (13 reviews)

10/10

Exceptional

(13 reviews)

"We had a nice stay. Kitchen well stocked and house was clean and comfortable."

Elaine A.

Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

A backyard with a swimming pool, wicker lounge chairs, and potted plants.

A wicker outdoor seating area with a dog on a cushioned bench.

A living room with a green sofa, a small round table with a board game, a blue vase with dried plants, and a white arched cabinet.

A garden with hydrangea bushes, a stone wall, and a covered area with plants.

18. Designer Sag Harbor Home w/ Pool + Fire Pit + Yard

Designer Sag Harbor Home w/ Pool + Fire Pit + Yard

Sag Harbor

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"excellent and convenient stay!! located close into town, perfect for the small family group I was traveling with. home was very clean, cozy, had everything we needed! backyard with pool was a dream, beautifully landscaped, plenty of seating, very clean pool, would stay again! thanks for a delightful escape!"

maria m.

The price is ￥89,229

￥89,229

￥175,303 total

includes taxes & fees

Oct 1 - Oct 2

Designer Sag Harbor Home w/ Pool + Fire Pit + Yard

A spacious, well-lit room with a high ceiling, large windows, and a cozy seating area with a sofa and chairs.

A room with a white bench, a small table with a lamp, and a window with a view of greenery.

A bedroom with a large bed, wooden flooring, a dresser, a mirror, and a clock on the wall.

A stone-paved entrance with steps leading to a white door, surrounded by potted plants and a small garden.

19. Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

Saybrook Manor

9.8 out of 10, Exceptional, (140 reviews)

9.8/10

Exceptional

(140 reviews)

"This house comfortably sleeps a lot of guests and has a well equipped kitchen. Everything was very clean. The hosts were very easy to communicate with and very helpful."

Alexis L.

The price is ￥45,323

￥45,323

￥88,553 total

includes taxes & fees

Oct 12 - Oct 13

Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

An aerial view of a coastal residential area with houses along the beach, a clear sky, and calm sea.

A modern kitchen with a granite island, stainless steel appliances, and a bar area with bar stools.

A bedroom with a large bed, wooden wardrobe, and a TV on the wall.

A spacious living room with a wooden dining table, gray sofa, and a large window.

20. Beachside Bliss w/ Game Room, Gym & Golf Green

Beachside Bliss w/ Game Room, Gym & Golf Green

Westbrook

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

"Perfect house for 6 guests. Loved that it was close to the beach."

Shannon G.

The price is ￥42,411

￥42,411

￥106,725 total

includes taxes & fees

Oct 20 - Oct 21

Beachside Bliss w/ Game Room, Gym & Golf Green

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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Top Greenport Hotel Reviews

Saybrook Point Resort & Marina

8/10 Good

"The staff are very welcoming. A small point but the hot water in the bathroom is just warm and takes a time to arrive...."

David 2-night trip

Posted 6 hours ago

Saybrook Point Resort & Marina

Hyatt Place Long Island East End

10/10 Excellent

"Very beautiful very clean. Staff was amazing."

Savannah 2-night trip

Posted 10 hours ago

Hyatt Place Long Island East End

Ocean Vista Resort

10/10 Excellent

"The beach was perfect"

Igor 1-night trip

Posted 23 hours ago

Ocean Vista Resort

Water's Edge Resort & Spa

10/10 Excellent

"I felt very comfortable and at ease. I had planned on getting a massage, but never made it. Next time I will book one. The beds were comfortable. The food was good, I enjoyed myself."

LOUISE 2-night trip

Posted 1 day ago

Water's Edge Resort & Spa

North Fork Resort

10/10 Excellent

"Fantastic contemporary cottage. Looks brand new and it has everything. Wonderful place to stay. Check in process needs improvement with more attention paid to details by staff."

marie 1-night trip

Posted 1 day ago

North Fork Resort

The Harbor Front Inn

10/10 Excellent

"The hotel was just what we expected, cozy and comfortable and nestled right into central Greenport. Close to everything, dinner spots just steps away. Will definitely return."

Arnold 2-night trip

Posted 2 days ago

The Harbor Front Inn

Silver Sands Motel & Beach Bungalows

10/10 Excellent

"This is a great place that brings you back to a special time. Staff were exceptionally friendly and helpful. Made us feel like we were family - highly recommend."

Keith 3-night trip

Posted 2 days ago

Silver Sands Motel & Beach Bungalows

Oyster Estate

10/10 Excellent

"Newly renovated. Place looks great."

john 2-night trip

Posted 10 days ago

Oyster Estate

American Beech Hotel

10/10 Excellent

"Fun picnic breakfast left at the door at 9am"

Peter 1-night trip

Posted 2 weeks ago

American Beech Hotel

Find out more about Greenport

Greenport Vacation Homes information

Number of reviews	516
Accommodation	1236 Vacation Homes
Lowest Price	￥43,661
Highest Price	￥213,541

Explore a world of travel with Expedia

More ways to book

Book Vacation Homes in Greenport on Expedia.com

Search Vacation Homes in Greenport

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Greenport vacation homes

1. Aqua Vista

2. The SandPiper

3. American Beech in Greenport - Petite King Room 7

4. Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

5. Beach Block Hideaway

6. Northfork Townhouse walk to all

7. Renovated Townhouse walk to all

8. Beachfront Greenport Villa

9. American Beech in Greenport - Deluxe King 6

10. Insta-worthy Couples Retreat: Perfect for romantic getaway!

11. Work and Play Special! Extended Stay Discount

12. Great Hammcock Getaway, cozy home, hot tub, fire pit, beaches nearby.

13. The Bay Cottage · Rocky Neck Park, Beach & Niantic

14. Huge Island Getaway Pool Hot Tub Walk To Beach

15. Adorable Cottage, 5 min walk to water & town

16. Year round Jacuzzi - Blackberry Home

17. Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

18. Designer Sag Harbor Home w/ Pool + Fire Pit + Yard

19. Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

20. Beachside Bliss w/ Game Room, Gym & Golf Green

Find vacation rentals that suit your style

Top Greenport Hotel Reviews

Saybrook Point Resort & Marina

Find out more about Greenport

Greenport Vacation Homes information

Explore a world of travel with Expedia