10 Best Greenport Condos on Holiday Lettings - House rentals

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13 Vacation rentals

25

Home rental in Greenport

North Fork / Greenport

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Built in 1828 for a ship’s captain, this historic property remains as one of the oldest structures in the village. Original details abound. Large, bright & airy rooms. Brand new furnishings. Perfect for entertaining or a quiet weekend retreat. The Space Located on a …see more

from $225 / night

$3500 - $5500 / week

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Responds fast!
avg. 2 hours 25 minutes

from $225 / night

(7) Excellent 

14

Vacation apartment in Greenport

North Fork / Greenport

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
Overview: Waterfront Water's Edge suite, Suite C-204, accommodates up to 6 guests (see below) with two bedrooms and two bathrooms located on the North Fork of Long Island at The Cliffside Resort Condominiums in Greenport, New York. Quoted rental rates include all taxes …see more

from $300 / night

$2100 - $2600 / week

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from $300 / night

26

Apartment rental in Greenport

North Fork / Greenport

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Suitable for children age 5+
  • Air conditioning
Explore the historic seaport of Greenport Village from this recently remodeled 1-bedroom, 1-bathroom vacation rental apartment that comfortably sleeps 2. Located in the heart of downtown, you won’t find a better location to explore all the area has to offer than from th …see more

from $185 / night

$1295 - $2205 / week

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Responds fast!
avg. 1 hour 45 minutes

from $185 / night

8

Greenport Vacation farmhouse accommodation

North Fork / Greenport

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Ask about pets
Historic Greenport Village has been recently renovated and is in walking distance to all. This is a 2 family home that can be rented separately or together. Pricing here is for house 2. One bedroom has a queen and the other can be configured as a king or two twins. Park …see more

from $400 / night

$2800 / week

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from $400 / night

(1) Very Good 

10

Vacation home in Greenport

North Fork / Greenport

5 14 Min stay varies

  • 5 bedrooms
  • Sleeps 14
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Renovated and tastefully furnished, The Farmhouse features one of the largest wrap around porches in the village and it is enviably located steps away from the town's best restaurants and bars, as well as just 3 short blocks to the beach. The space Just steps away fro …see more

from $600 / night

$4000 - $10625 / week

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Responds fast!
avg. 2 hours 25 minutes

from $600 / night

22

Vacation home in Greenport

North Fork / Greenport

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
You will love this 4 bedroom 4.5 bathroom charmer on a quiet street. Walk to town, shops, carousel LIRR Jitney and ferry to Shelter Island Golf course and beaches 1 mile away. There are over 40 wineries nearby. The front deck has 2 Adirondack chairs to just relax. A f …see more

from $700 / night

$3800 / week

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from $700 / night

13

Vacation farmhouse rental

North Fork / Greenport

3 6 14 nights min

  • 3 bedrooms
  • Sleeps 6
  • 14 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Entirely renovated, spacious and quiet farmhouse two blocks from the marina, and a 5 minute bike ride to the beach or town. With original hardwood floors, modern kitchen with Viking appliances, two fireplaces, grill, and al fresco dining under a pergola. Located in Gree …see more

from $425 / night

$2975 / week

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from $425 / night

16

Vacation farmhouse in Greenport

North Fork / Greenport

3 8 30 nights min

  • 3 bedrooms
  • Sleeps 8
  • 30 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
Historic home in Greenport Village walking distance to restaurants, water, shopping etc..bike or short drive from vineyards. Large yard with outdoor patio with BBQ and outdoor shower. 2 family home with two separate duplex units that can be rented separately or together …see more

from $517 / night

$3617 / week

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from $517 / night

16

Vacation home in Greenport

North Fork / Greenport

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Air conditioning
  • Ask about pets
  • Private garden
Walking distance to Greenport Village, Sound and Bay Beaches! 1200 sq ft Victorian cottage perfect for a retreat from the heat. Large patio, new kitchen and bath! 1840s historic poet's house, perfect for couples, small family or single seeking reprieve from Manhattan. …see more

from $234 / night

$1634 / week

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Responds fast!
avg. 1 hour 27 minutes

from $234 / night

18

Vacation home in Greenport

North Fork / Greenport

2 4 6 nights min

  • 2 bedrooms
  • Sleeps 4
  • 6 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Designed and built in 2003, this cozy house has water views of Peconic Bay, enormous glass skylights, fully equipped kitchen, two bedroom, two bath, washer, dryer, Wifi, flat screen tv, private rose garden, private parking, a kayak, two bicycles, public swimming dock at …see more

from $357 / night

$2500 / week

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Responds fast!
avg. 3 hours 51 minutes

from $357 / night

26

Apartment rental in Greenport

North Fork / Greenport

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Suitable for children age 5+
  • Air conditioning
Escape to the scenic seaside village of Greenport in this 2-bedroom, 2-bathroom vacation rental apartment that comfortably sleeps 4. Located in the heart of Greenport Village, enjoy quick access to fine restaurants, exceptional shopping and numerous local attractions. B …see more

from $285 / night

$1995 - $3115 / week

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Responds fast!
avg. 1 hour 45 minutes

from $285 / night

30

Greenport Vacation apartment rental

North Fork / Greenport

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Suitable for children age 5+
  • Air conditioning
Explore the charming seaside village of Greenport from this quaint 1-bedroom, 1-bathroom vacation rental apartment with sleeping accommodations for 2. Only a couple of blocks from downtown, enjoy quick access to numerous restaurants, boutique shops and local attractions …see more

from $155 / night

$1085 - $1645 / week

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avg. 1 hour 45 minutes

from $155 / night

19

Greenport Vacation home accommodation

North Fork / Greenport

5 9 1 night min

  • 5 bedrooms
  • Sleeps 9
  • 1 night min
  • Child friendly
  • Air conditioning
  • Private garden
Elegant and especially designed and built for one of the wealthiest bankers on the North Fork. Situated on enormous 3/4 acre property in the most prestigious setting of the National Historic District in Greenport Village. Lovingly restored to its original elegance an …see more

from $850 / night

$6500 / week

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from $850 / night