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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 5 – 12

G$107,355 GYD 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.

Aug 5 – 12

G$182,865 GYD per night

Home in East Haven

4.88 out of 5 average rating, 196 reviews

Beach Cottage by the Sea

Beautiful 1920's beach cottage with beach access just across the street. Enjoy the sea breeze, ocean views, and sound of the waves lapping in this quaint home with unique architecture. Ten minutes to downtown New Haven and Yale for great places to eat, museums, and nightlife. Public beach and playground nearby. Warm and welcoming community. Master bedroom has vaulted ceilings and deck with views of the sea. Central Air, Cable TV, outdoor grill, plenty of parking. Enjoy this lovely home!

Apr 4 – 11

G$32,434 GYD 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.

Apr 13 – 20

G$90,224 GYD 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 24 – 31

G$21,223 GYD per night

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).

Feb 1 – 8

G$25,448 GYD per night

Home in Cutchogue

4.96 out of 5 average rating, 190 reviews

Stunning Vinyard Views - Spring Special $475/Nt!

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.

Dec 31 – Jan 7

G$173,478 GYD 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

G$94,999 GYD 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.

Sep 26 – Oct 3

G$123,233 GYD per night

Home in Greenport

4.98 out of 5 average rating, 144 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.

May 10 – 17

G$160,330 GYD 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

G$119,638 GYD 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 14 – 21

G$41,294 GYD 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

May 23 – 30

G$192,266 GYD per night

Home in Hampton Bays

4.98 out of 5 average rating, 112 reviews

Beach House Feel - newly renovated backyard Oasis

Jul 19 – 26

G$175,831 GYD per night

Home in Sag Harbor

4.85 out of 5 average rating, 250 reviews

Exclusive Sag Harbor Compound

Nov 26 – Dec 3

G$145,234 GYD per night

Home in East Hampton

4.93 out of 5 average rating, 141 reviews

1800 Historical East Hampton Home, 1 Mile to Town!

Jan 15 – 22

G$120,087 GYD per night

Home in Sag Harbor

4.89 out of 5 average rating, 166 reviews

Kiddo Approved! Heated Pool/Hotub Renovated Home

Oct 18 – 25

G$97,132 GYD per night

Home in East Hampton

4.97 out of 5 average rating, 116 reviews

Explore the Water & Woods at a Relaxing Retreat

Nov 8 – 15

G$190,565 GYD per night

Home in East Hampton

4.87 out of 5 average rating, 188 reviews

Heated Saltwater Pool, Walk to Beach, Dog Friendly

Oct 31 – Nov 7

G$47,348 GYD per night

Home in East Hampton

4.92 out of 5 average rating, 128 reviews

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

Oct 23 – 30

G$144,357 GYD 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

Jan 21 – 28

G$116,368 GYD per night

Home in Greenport

5.0 out of 5 average rating, 36 reviews

Beachfront Greenport Villa

Jan 22 – 29

G$124,163 GYD per night

Home in Greenport

4.96 out of 5 average rating, 28 reviews

Walk to town, Greenport Village - Harbor Views

Oct 7 – 14

G$126,796 GYD per night

Home in Greenport

5.0 out of 5 average rating, 10 reviews

The Sandy Shack - Coastal Escape

Nov 5 – 12

G$136,676 GYD per night

Home in Greenport

5.0 out of 5 average rating, 10 reviews

The Saltbox: Outdoor Dining, Fire Pit, Soaking Tub

Sep 24 – Oct 1

G$121,357 GYD per night

Home in Greenport

4.99 out of 5 average rating, 71 reviews

Beach House in L.I. Wine Country

Oct 24 – 31

G$100,455 GYD per night

Home in Mattituck

4.92 out of 5 average rating, 92 reviews

Modern Farmhouse Steps to Beach & Love Lane

Apr 3 – 10

G$98,390 GYD per night

Home in Greenport

5.0 out of 5 average rating, 3 reviews

Waterfront Greenport Boathouse

Jan 3 – 10

G$130,540 GYD per night

Weekly house rentals

Home in Southold

5.0 out of 5 average rating, 17 reviews

Le Petit Cottage Southold NY

Feb 7 – 14

G$46,090 GYD per night

Home in East Marion

4.83 out of 5 average rating, 6 reviews

Private North Fork Cottage- Walk to Beach!

Nov 5 – 12

G$50,005 GYD 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

G$134,897 GYD per night

Home in Greenport

4.96 out of 5 average rating, 24 reviews

Victorian Pearl

Mar 21 – 28

G$55,883 GYD per night

Home in Greenport

4.93 out of 5 average rating, 80 reviews

Chic greenport village home

Nov 6 – 13

G$100,306 GYD per night

Home in Greenport

4.91 out of 5 average rating, 86 reviews

North Fork Escape - Walk To Village, Beach, Parks

Feb 26 – Mar 5

G$112,992 GYD per night

Home in Greenport

4.91 out of 5 average rating, 22 reviews

Greenport Getaway - North Fork Rental

Jul 15 – 22

G$146,984 GYD per night

Home in Greenport

4.94 out of 5 average rating, 86 reviews

Maritime Village Getaway with Backyard

Apr 15 – 22

G$98,109 GYD 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
G$31,348 GYD before taxes and fees

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