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House vacation rentals in Greenport

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Top-rated house rentals in Greenport

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Home in Greenport

4.83 out of 5 average rating, 190 reviews

The Greenport Townhouse - Amazing Location & Large Backyard

The house is located on a .35 acre lot with plenty of outdoor dining space and a huge grass area with a firepit & hammock. There are 2 floors. The first floor has an open floor plan with a connecting kitchen, dining room, and living room. The kitchen is well equipped with a dish washer, electric stove/oven, refrigerator, and coffee bar. There is also a bedroom on the 1st floor with 2 full-sized beds. The 2nd floor has 3 bedrooms and a loft/den area. The three bedrooms on this floor have 1 queen bed+futon, 2 full-sized beds, and 2 twin beds (which can be made together to form a king upon request), respectively. All rooms have AC. There are 2 full bathrooms (1 on each floor) and a washer/dryer. Guests have access to the entire house and backyard area. We respect your privacy, but we are accessible if you have questions or need anything throughout your stay. Greenport was voted one of the prettiest towns in America by Forbes magazine. It has a vibrant and relaxing culture, offering access to beaches, wine tasting, and wonderful restaurants. The Shelter Island Ferry and Hampton Jitney stops are nearby. We are just a few short blocks from the Hampton Jitney stop, the LIRR station, and the Shelter Island Ferry. No car necessary - you can walk wherever you need!

Apr 7 – 14

R9,780 ZAR per night

Home in Greenport

4.92 out of 5 average rating, 121 reviews

Beautiful Cottage Home W/ Beach & Dock Access

Beautiful, spacious beach side home situated within a block of a private beach. This cozy home is walking distance to Kontokosta Winery, Island's End Golf & Country Club, Lavender By the Bay and a five minute drive to the Village of Greenport. Replete with natural light and an open backyard perfect for outdoor dining and barbecues, this home is perfect for your stay in Greenport. Netflix/Hulu/Disney+ / ESPN+ / HBO MAX. Please note, 4 Bikes/1 Paddle Board/1 Kayak & Life Jackets provided May-Sept.

Sep 22 – 29

R16,499 ZAR per night

Home in Greenport

4.98 out of 5 average rating, 85 reviews

Designer's Dream - Charming Boathouse

An architect's and interior decorator's dream home! This home is a historic boathouse built in the late 1890's, and recently & lovingly fully renovated and restored. In the middle of Greenport Village - walking distance to train station, Jitney stop, and Shelter Island Ferry as well as the best North Fork restaurants, vineyards, bars, and beaches. Two bedroom home with ground floor fireplace, outdoor shower (not enclosed), and beautifully landscaped outside patio w/grilling & dining areas.

Sep 26 – Oct 3

R8,453 ZAR per night

Home in Holbrook

4.91 out of 5 average rating, 237 reviews

Cozy studio

We are 10 minutes away to MacArthur Airport in Islip, 5 minutes to shopping center where you can find supermarkets, restaurants, and stores. We are 10 minutes away from LIRR train station where you can get a ride to Manhattan. Although the studio is centrally located a car or Uber is recommended,. You'll have your own bathroom, kitchen with microwave, coffee maker, toaster, fridge, air conditioner, tv with cable and internet. Our study is a FREE SMOKING PLACE! Not smoking or vaping!

Jul 28 – Aug 4

R1,920 ZAR per night

Home in Greenport

4.94 out of 5 average rating, 136 reviews

Harbor Heights

Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney. My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

Jan 13 – 20

R1,481 ZAR per night

Home in Cutchogue

4.96 out of 5 average rating, 190 reviews

Private Oasis W/Stunning Vinyard And Pool Views

Enjoy spectacular wine country sunset views from the living room that extend to the gorgeous saltwater gunite pool and spa. (Please note THE POOL AND SPA (attached hot tub) are OPEN FROM MAY 1 - OCTOBER 15 only). Beautifully decorated, comfortable home with an updated chef's kitchen and fireplace. Fabulous restaurants, wineries, farms, beaches and exquisite small towns all nearby. Simply put, a magical, peaceful paradise for you and your group.

Mar 7 – 14

R15,674 ZAR per night

Home in Greenport

4.97 out of 5 average rating, 223 reviews

The Greenport Bungalow

Sweet Modern Bungalow Walking Distance to Town Located in the historic town of Greenport Village - 8 min walk to the beach, center of town, Shelter Island Ferry and LIRR... A newly built sun filled 3 bedroom house with all the amenities you would need when renting a home. Enjoy the large and fenced in back yard after a fun day in this historic Long Island fishing village. Great restaurants, and even better locally produced wine and beer!

Jun 9 – 14

R8,579 ZAR per night

Home in Sag Harbor

4.97 out of 5 average rating, 260 reviews

Sag Harbor Cottage, Walk to the Beach!

Renovated to perfection, this fully equipped fresh & modern beach cottage has an open-plan living room, dining room & kitchen, all with high ceilings, immaculate finishings, & a sunny lower level TV room. A broad mahogany deck with large outdoor shower & gas BBQ grill runs the full length of the house & overlooks a roomy lawn with great privacy, fire pit and mature landscaping.

Oct 15 – 22

R6,865 ZAR per night

Home in Greenport

4.98 out of 5 average rating, 145 reviews

Greenport Village walking distance to all

Large spacious home in the heart of wine country. Roomy den for relaxing after the wineries. Screened in patio for al fresco dining and enjoying the spacious yard. Hot tub operational year round! Strong, fast wifi with multiple extenders. Message me with any questions or for special offers on 4/5 day stays or midweek 2/3 night specials.

Nov 27 – Dec 4

R16,011 ZAR per night

Home in Old Lyme

4.96 out of 5 average rating, 129 reviews

Modern Farmhouse with Hot Tub in Old Lyme, CT

Originally built in 1856 this farmhouse has been lovingly restored with stylish and modern amenities for a perfect vacation getaway. Nestled in the heart of downtown, historic Old Lyme the property is convenient to shops, restaurants and local shoreline activities including water sports and hiking.

Jan 26 – Feb 2

R7,472 ZAR per night

Home in Greenport

4.98 out of 5 average rating, 165 reviews

Nofo Bungalow-In The Heart of Greenport Village

This historic Greenport home has been completely renovated . The Bungalow is in the heart of Greenport Village on a quiet dead end. The home includes 1500 square feet of open concept living, two bedrooms, and two full baths. The downstairs bedroom features a queen and upstairs bedroom four twins.

Sep 4 – 11

R10,799 ZAR per night

Home in Greenport

4.91 out of 5 average rating, 54 reviews

Greenport Village Relaxation

Celebrate each season with an escape Out East. To explore the North Fork there is no other place you can be than in the heart of Greenport Village. This 1930's Historic District cottage checks all the boxes for your ideal weekend getaway. Nothing but the best in food, wine and water.

May 13 – 20

R3,733 ZAR per night

Vacation rentals for every style

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Popular amenities for Greenport house rentals

Free parking on premises

Air conditioning

House rentals with a pool

Home in Sag Harbor

4.94 out of 5 average rating, 102 reviews

Sag Harbor Village Cottage with Pool

Jun 11 – 18

R19,358 ZAR per night

Home in Hampton Bays

4.98 out of 5 average rating, 112 reviews

Beach House Feel - newly renovated backyard Oasis

Oct 25 – Nov 1

R10,065 ZAR per night

Home in Water Mill

4.91 out of 5 average rating, 110 reviews

Beach Barn w/ Sauna and Heated Pool - Dog Friendly

Nov 12 – 19

R18,393 ZAR per night

Home in Sag Harbor

4.85 out of 5 average rating, 250 reviews

Exclusive Sag Harbor Compound

Dec 8 – 15

R9,885 ZAR per night

Home in East Hampton

4.93 out of 5 average rating, 141 reviews

1800 Historical East Hampton Home, 1 Mile to Town!

Nov 15 – 22

R15,144 ZAR per night

Home in Southampton

4.95 out of 5 average rating, 132 reviews

Waterview, PoolOpenNow! DogsFree+Kayaks+PingPong

Mar 28 – Apr 4

R7,706 ZAR per night

Home in Manorville

4.99 out of 5 average rating, 201 reviews

Ultimate House with Heated Pool, Hot Tub and Sauna

Oct 18 – 25

R10,861 ZAR per night

Home in East Hampton

4.97 out of 5 average rating, 116 reviews

Explore the Water & Woods at a Relaxing Retreat

Nov 16 – 23

R19,201 ZAR per night

House rentals with free parking

Home in Greenport

5.0 out of 5 average rating, 30 reviews

Historic Stunner in Heart of Village

Aug 9 – 16

R12,237 ZAR per night

Home in Greenport

5.0 out of 5 average rating, 19 reviews

The Corwin House

May 10 – 17

R14,650 ZAR per night

Home in Greenport

5.0 out of 5 average rating, 10 reviews

The Saltbox: Outdoor Dining, Fire Pit, Soaking Tub

Oct 7 – 14

R9,781 ZAR per night

Home in Greenport

5.0 out of 5 average rating, 36 reviews

Beachfront Greenport Villa

Jan 29 – Feb 5

R11,210 ZAR per night

Home in Greenport

4.96 out of 5 average rating, 28 reviews

Walk to town, Greenport Village - Harbor Views

Dec 15 – 22

R11,446 ZAR per night

Home in Southold

5.0 out of 5 average rating, 10 reviews

Gorgeous home with heated gunnite pool!

Mar 27 – Apr 3

R8,210 ZAR per night

Home in Greenport

5.0 out of 5 average rating, 10 reviews

The Sandy Shack - Coastal Escape

Nov 7 – 14

R12,337 ZAR per night

Home in Greenport

4.99 out of 5 average rating, 72 reviews

Beach House in L.I. Wine Country

Oct 24 – 31

R9,073 ZAR per night

House rentals with a hot tub

Home in East Hampton

4.97 out of 5 average rating, 120 reviews

East Hampton (walking distance to village)

Nov 20 – 27

R13,225 ZAR per night

Home in Wading River

4.96 out of 5 average rating, 457 reviews

Your Zen Retreat

Aug 19 – 26

R9,588 ZAR per night

Home in Southampton

4.82 out of 5 average rating, 199 reviews

Cozy & Chic Summer Getaway near village/beaches

Jun 4 – 11

R13,965 ZAR per night

Home in Center Moriches

4.98 out of 5 average rating, 189 reviews

Walk to beach and playground. Outdoor hot tub.

Oct 6 – 13

R6,793 ZAR per night

Home in Westhampton Beach

4.93 out of 5 average rating, 134 reviews

Hampton's Haven

Oct 30 – Nov 6

R14,570 ZAR per night

Home in Hampton Bays

4.94 out of 5 average rating, 111 reviews

Beautiful Hampton’s Home Pool/Tennis/HotTub/Sauna

Mar 27 – Apr 3

R18,501 ZAR per night

Home in Shirley

4.98 out of 5 average rating, 204 reviews

By NYC & Hamptons - Hot Tub, Pool Table, Speakeasy

Sep 3 – 10

R10,712 ZAR per night

Home in Southold

4.92 out of 5 average rating, 12 reviews

Beach/Lake house Fireplace & Hot Tub, By Wineries

Jun 11 – 18

R12,181 ZAR per night

Quick stats about house rentals in Greenport

Total rentals
90 properties
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
30 properties allow pets
Family-friendly rentals
80 properties are a good fit for families
Total number of reviews
4.6K reviews
Nightly prices starting at
R2,772 ZAR before taxes and fees

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