15 Best Greenport Condos on Holiday Lettings - House rentals

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289 Vacation rentals

24

Home rental in Greenport

North Fork / Greenport

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Child friendly
  • Air conditioning
Spend your summer days in Long Island as you relax in 'Jason's Haven,' a 3-bedroom, 1-bathroom vacation rental home that sleeps 6. Nestled within the historical town of Greenport, this home provides a unique New York experience, sans big buildings and bustling sidewalks …see more

from $260 / night

$1,820 / week

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Responds fast!
avg. 16 minutes

from $260 / night

(10) Excellent 

Certificate of Excellence

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

Certificate of Excellence

from $325 / night

$2,200 - $2,800 / week

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Responds fast!
avg. 3 hours 40 minutes

from $325 / night

23

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 $194 / night

$1,358 / week

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Responds fast!
avg. 16 minutes

from $194 / night

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 $300 / night

$3,500 - $5,000 / week

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Responds fast!
avg. 3 hours 43 minutes

from $300 / 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

$2,975 / week

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from $425 / night

(1) Very Good 

15

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 $725 / night

$6,400 - $10,625 / week

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Responds fast!
avg. 3 hours 43 minutes

from $725 / night

20

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

$4,900 / week

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from $700 / 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

$2,800 / week

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from $400 / 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

$2,500 / week

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Responds fast!
avg. 3 hours 51 minutes

from $357 / night

17

Vacation home in Greenport

North Fork / Greenport

4 11 2 nights min

  • 4 bedrooms
  • Sleeps 11
  • 2 nights min
1903 Village Farmhouse, full of character, light and air. A place to relax, unwind and drink wine on the front porch, say hello to our neighbors or take an afternoon nap. Walk into the village for shopping and dinner or ride your bike to the beach. Visit one of the m …see more

from $400 / night

$3,000 - $5,000 / week

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from $400 / night

22

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 $170 / night

$1,190 / week

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Responds fast!
avg. 16 minutes

from $170 / night

(2) Excellent 

32

Greenport Vacation home accommodation

North Fork / Greenport

5 8 Min stay varies

  • 5 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 1 mi
  • Child friendly
  • Car not necessary
Elegant and especially designed and built for one of the wealthiest bankers on the North Fork. Situated on enormous property in the most prestigious setting of the National Historic District in Greenport Village. Lovingly restored to its original elegance and authent …see more

from $850 / night

$6,500 / week

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from $850 / night

24

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 $299 / night

$2,093 / week

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Responds fast!
avg. 16 minutes

from $299 / 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

$3,617 / week

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from $517 / night

13

Vacation home in Greenport

North Fork / Greenport

3 6 14 nights min

  • 3 bedrooms
  • Sleeps 6
  • 14 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Newly renovated ranch private home with spacious deck, large teak dining set, new grill, CAC, washer/dryer, front porch, fully equipped kitchen, wall mounted flat screen TVs in every bedroom and family room, farm dining room table. Nicely appointed home within walking …see more

from $461 / night

$3,227 / week

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from $461 / night

16

Vacation home in Greenport

North Fork / Greenport

2 4 60 nights min

  • 2 bedrooms
  • Sleeps 4
  • 60 nights min
  • 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 $334 / night

$2,334 / week

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Responds fast!
avg. 2 hours 24 minutes

from $334 / night