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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!

Dec 25 – Jan 1

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 19 – 26

Home in Shelter Island

4.97 out of 5 average rating, 197 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.

Dec 5 – 12

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.

Dec 10 – 17

Home in East Lyme

4.96 out of 5 average rating, 105 reviews

Walk to the beach at Black Point, Niantic, Ct

Black Point beach home (5th house from water) within walking distance of three beaches. Open floor plan with three levels. Ping Pong room on lower level. Living room, dining room, sitting area, and kitchen on mid level. Three bedrooms & 2 full bath on top level. WI-Fi, linens, coffee, water provided. Fenced in back yard with gas grill. Close to casinos, charter fishing, Essex steam train, Mystic Aquarium & Seaport, and Newport (1 Hr). Walk Niantic Bay Boardwalk or Old Black Point.

Jan 1 – 8

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).

Jan 29 – Feb 5

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.

Oct 29 – Nov 5

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

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!!!

Mar 17 – 24

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.

Aug 29 – Sep 5

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

Home in Old Lyme

4.96 out of 5 average rating, 128 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.

Feb 8 – 15

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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

Home in Hampton Bays

4.98 out of 5 average rating, 112 reviews

Beach House Feel - newly renovated backyard Oasis

Sep 17 – 24

Home in East Hampton

4.93 out of 5 average rating, 141 reviews

1800 Historical East Hampton Home, 1 Mile to Town!

May 5 – 12

Home in Sag Harbor

4.85 out of 5 average rating, 250 reviews

Exclusive Sag Harbor Compound

Dec 6 – 13

Home in Sag Harbor

4.89 out of 5 average rating, 166 reviews

Kiddo Approved! Heated Pool/Hotub Renovated Home

May 7 – 14

Home in Water Mill

4.91 out of 5 average rating, 110 reviews

Beach Barn w/ Sauna and Heated Pool - Dog Friendly

Jan 1 – 8

Home in Manorville

4.99 out of 5 average rating, 201 reviews

Ultimate House with Heated Pool, Hot Tub and Sauna

Oct 20 – 27

Home in East Hampton

4.97 out of 5 average rating, 116 reviews

Explore the Water & Woods at a Relaxing Retreat

Dec 31 – Jan 7

House rentals with free parking

Home in Greenport

5.0 out of 5 average rating, 30 reviews

Historic Stunner in Heart of Village

Nov 19 – 26

Home in Greenport

4.91 out of 5 average rating, 54 reviews

Greenport Village Relaxation

May 13 – 20

Home in Greenport

4.96 out of 5 average rating, 28 reviews

Walk to town, Greenport Village - Harbor Views

Nov 8 – 15

Home in Greenport

5.0 out of 5 average rating, 10 reviews

The Sandy Shack - Coastal Escape

Nov 4 – 11

Home in Southold

5.0 out of 5 average rating, 10 reviews

Gorgeous home with heated gunnite pool!

Jan 22 – 29

Home in Greenport

4.95 out of 5 average rating, 20 reviews

Walk to Beach or to Town …

Nov 16 – 23

Home in Greenport

4.99 out of 5 average rating, 71 reviews

Beach House in L.I. Wine Country

Oct 24 – 31

Home in Greenport

5.0 out of 5 average rating, 10 reviews

The Saltbox: Outdoor Dining, Fire Pit, Soaking Tub

Sep 24 – Oct 1

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

Home in Wading River

4.96 out of 5 average rating, 457 reviews

Your Zen Retreat

May 5 – 10

Home in Center Moriches

4.98 out of 5 average rating, 189 reviews

Walk to beach and playground. Outdoor hot tub.

Sep 27 – Oct 4

Home in Southampton

4.82 out of 5 average rating, 199 reviews

Cozy & Chic Summer Getaway near village/beaches

Jun 1 – 8

Home in Westhampton Beach

4.93 out of 5 average rating, 134 reviews

Hampton's Haven

Oct 30 – Nov 6

Home in Hampton Bays

4.94 out of 5 average rating, 111 reviews

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

Mar 14 – 21

Home in Shirley

4.98 out of 5 average rating, 203 reviews

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

Sep 26 – Oct 3

Home in Southold

4.92 out of 5 average rating, 12 reviews

Beach/Lake house Fireplace & Hot Tub, By Wineries

Jun 11 – 18

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
$150 before taxes and fees

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