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House holiday 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!

8–15 Apr

$920 NZD per night

Guest favourite

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.

30 Jul – 6 Aug

$1,481 NZD per night

Guest favourite

Home in Shelter Island

4.97 out of 5 average rating, 198 reviews

Huge Island Getaway Pool HotTub Walk To Beach

Relaxation begins on the 6 minute ferry ride to this magical island. Summerfield is a spectacular, grand compound that has it all. Huge main house great for groups, 4700ft w/ privacy for all overlooking serene nature reserve. Star gaze in the bubbling hot tub, grill outside after a swim, play in the rec room with movie theater, pool table or ping pong,or watch TV by the fire! Open plan layout, gourmet kitchen, heated gunite pool, separate guest house. Prime location close to beach + restaurants.

28 Feb – 7 Mar

$1,757 NZD per night

Guest favourite

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.

4–11 Oct

$766 NZD per night

Guest favourite

Home in Brookhaven

4.95 out of 5 average rating, 129 reviews

Beautiful & Independent Guest House near the water

Welcome to our beautiful yet very private guest house in Brookhaven. You are walking distance from the Deer Run Farm (fresh eggs every morning), Post-Morrow Nature Trails and a short drive to Bellport Village Historic District. We are also very close to Wine Country, The Hamptons & Fire Island. We offer all the accommodations you might need for longer stays Washer & Dryer; Dishwasher; High Speed internet and TVs with all the premium channels. EV Charger available (Tesla - Fees applies).

31 Mar – 7 Apr

$308 NZD per night

Guest favourite

Home in Greenport

4.92 out of 5 average rating, 423 reviews

Blue Bay Dream

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).

25 Jan – 1 Feb

$227 NZD per night

Guest favourite

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.

2–9 Jan

$1,502 NZD per night

Guest favourite

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!

9–14 Jun

$802 NZD per night

Home in Shelter Island

4.89 out of 5 average rating, 106 reviews

Hay Beach Getaway!

Welcome to our family-friendly oasis just two blocks from beautiful beaches! Our house offers an open space living area, an expansive yard, fire pits, and a basement with a playroom and workout area. Enjoy our quiet neighborhood. We provide kid-friendly toys, beach gear, bicycles, and more. Sleeps six, with additional options available for larger parties. Monday-Thursday stays February through June no cleaning fees!!!

21–28 Mar

$1,427 NZD per night

Guest favourite

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.

15–22 Oct

$645 NZD per night

Guest favourite

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.

11–18 Oct

$1,473 NZD per night

Guest favourite

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.

4–11 Sep

$989 NZD per night

Holiday rentals for every style

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Apartments

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Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Greenport house rentals

Free parking on premises

Air conditioning

House rentals with a pool

Guest favourite

Home in Hampton Bays

4.98 out of 5 average rating, 112 reviews

Beach House Feel - newly renovated backyard Oasis

18–25 Jul

$1,461 NZD per night

Guest favourite

Home in Sag Harbor

4.85 out of 5 average rating, 250 reviews

Exclusive Sag Harbor Compound

8–15 Dec

$926 NZD per night

Guest favourite

Home in East Hampton

4.93 out of 5 average rating, 141 reviews

1800 Historical East Hampton Home, 1 Mile to Town!

15–22 Nov

$1,385 NZD per night

Guest favourite

Home in Sag Harbor

4.89 out of 5 average rating, 167 reviews

Kiddo Approved! Heated Pool/Hotub Renovated Home

24–31 Oct

$976 NZD per night

Guest favourite

Home in Southampton

4.95 out of 5 average rating, 132 reviews

Waterview, PoolOpenNow! DogsFree+Kayaks+PingPong

26 May – 2 Jun

$1,553 NZD per night

Guest favourite

Home in East Hampton

4.87 out of 5 average rating, 188 reviews

Heated Saltwater Pool, Walk to Beach, Dog Friendly

27 Dec – 3 Jan

$663 NZD per night

Guest favourite

Home in East Hampton

4.97 out of 5 average rating, 116 reviews

Explore the Water & Woods at a Relaxing Retreat

16–23 Nov

$1,764 NZD per night

Guest favourite

Home in East Hampton

4.92 out of 5 average rating, 128 reviews

Heated pool, games room, near beach, kid-friendly

23–30 Oct

$1,222 NZD per night

Weekly house rentals

Home in Greenport

4.91 out of 5 average rating, 54 reviews

Greenport Village Relaxation

13–20 May

$365 NZD per night

Guest favourite

Home in Greenport

5.0 out of 5 average rating, 30 reviews

Historic Stunner in Heart of Village

7–14 Aug

$1,108 NZD per night

Guest favourite

Home in Greenport

4.96 out of 5 average rating, 28 reviews

Walk to town, Greenport Village - Harbor Views

16–23 Jan

$1,052 NZD per night

Guest favourite

Home in Greenport

5.0 out of 5 average rating, 36 reviews

Beachfront Greenport Villa

29 Jan – 5 Feb

$1,040 NZD per night

Home in Greenport

5.0 out of 5 average rating, 10 reviews

The Saltbox: Outdoor Dining, Fire Pit, Soaking Tub

7–14 Oct

$928 NZD per night

Guest favourite

Home in Greenport

5.0 out of 5 average rating, 10 reviews

The Sandy Shack - Coastal Escape

23–30 Dec

$1,131 NZD per night

Guest favourite

Home in Southold

5.0 out of 5 average rating, 11 reviews

Gorgeous home with heated gunnite pool!

27 Mar – 3 Apr

$784 NZD per night

Guest favourite

Home in Greenport

4.99 out of 5 average rating, 72 reviews

Beach House in L.I. Wine Country

24–31 Oct

$854 NZD per night

Private house rentals

Guest favourite

Home in Cutchogue

4.96 out of 5 average rating, 76 reviews

Secluded Farmhouse - Studio Apartment Style Unit

7–14 Feb

$537 NZD per night

Guest favourite

Home in Greenport

4.96 out of 5 average rating, 24 reviews

Victorian Pearl

3–10 Nov

$474 NZD per night

Guest favourite

Home in Greenport

4.95 out of 5 average rating, 20 reviews

Walk to Beach or to Town …

16–23 Nov

$707 NZD per night

Guest favourite

Home in Greenport

4.93 out of 5 average rating, 80 reviews

Chic greenport village home

9–16 May

$1,181 NZD per night

Guest favourite

Home in Cutchogue

4.97 out of 5 average rating, 31 reviews

Cozy Cottage with Views

20–27 Aug

$572 NZD per night

Guest favourite

Home in Southold

4.92 out of 5 average rating, 13 reviews

Beach/Lake house Fireplace & Hot Tub, By Wineries

11–18 Jun

$1,135 NZD per night

Guest favourite

Home in East Marion

4.95 out of 5 average rating, 99 reviews

Quiet, Upscale Retreat by the Beach

3–10 Oct

$810 NZD per night

Guest favourite

Home in Greenport

4.91 out of 5 average rating, 22 reviews

Greenport Getaway - North Fork Rental

24–31 May

$1,525 NZD 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
$250 NZD before taxes and fees

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