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House holiday rentals in Greenport West

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Top-rated house rentals in Greenport West

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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!

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.

Guest favourite

Home in Greenport

4.98 out of 5 average rating, 86 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.

Guest favourite

Home in Sag Harbor

4.89 out of 5 average rating, 167 reviews

Kiddo Approved! Heated Pool/Hotub Renovated Home

Family friendly Sag Harbor one level beach house close to Main Street. Heated pool (for a fee), hot tub, enclosed grass yard, kids play area with sandbox and toys, crib, highchair, outdoor fireplace, outdoor shower, yard is fenced and gated with separate safety fence for pool area. Backs up to a nature preserve for privacy. Quiet Neighborhood. Short drive to the beach and Main Street. Pool open April 13th-Oct 1. Pool can be heated June-August (for a fee). Hot Tub open April- November.

Guest favourite

Home in Greenport

4.96 out of 5 average rating, 110 reviews

Greenport Beach House

Modern 2-story home on the Long Island Sound with 125 ft private beach and one lush gated acre of land. The beach is easily accessed with just a few steps. Ideal for sunbathing, swimming, fishing & kayaking. Enjoy gorgeous sunset views on the beach and the spacious deck. BBQ area, with shed and outdoor shower with hot and cold water. *** New Check-out time. Check-in at 1 pm and Check-out by 7 pm. 4 bedrooms with queen-sized beds, a loft with 4 twins, and sleep space in the den.

Home in Greenport

5.0 out of 5 average rating, 3 reviews

Quaint Chalet w/Salt-heated Pool

A brand-new two-bedroom chalet that opens onto a heated, saltwater pool directly outside your patio doors. This is your ideal year-around gateway to experience Greenport. This private oasis is walking distance to Greenport Village, 4th & 5th Street beaches, as well as the train station and Jitney stop. Please note that the chalet has a spiral staircase for access to the second floor where the bedrooms are. The pool is open from Memorial Day weekend in May through Labor Day weekend.

Guest favourite

Home in East Marion

4.95 out of 5 average rating, 100 reviews

Quiet, Upscale Retreat by the Beach

We're on a quiet, tree-lined street, a lovely bike ride or walk from a pebble beach, with crystal clear water and stunning sunsets. Our house is the ideal base to explore the North Fork, where bucolic farmland abuts magnificent beaches. We're 5 minutes by car or 15 by bike to the charming seaside villages of Greenport and Orient. Our house is fully stocked, newly renovated and the spacious backyard borders 10 acres of lovely forest preserve. No large groups of unrelated adults.

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).

Guest favourite

Home in Greenport

4.97 out of 5 average rating, 224 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!

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!!!

Guest favourite

Home in Sag Harbor

4.96 out of 5 average rating, 262 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.

Guest favourite

Home in Greenport

4.98 out of 5 average rating, 146 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.

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Popular amenities for house rentals in Greenport West

Free parking on premises

Air conditioning

House rentals with a pool

Guest favourite

Home in Cutchogue

4.96 out of 5 average rating, 190 reviews

Private Oasis W/Stunning Vinyard And Pool Views

Guest favourite

Home in Southampton

4.97 out of 5 average rating, 240 reviews

Stunning 3 bed 2 bath home W Pool

Guest favourite

Home in East Hampton

4.93 out of 5 average rating, 142 reviews

1800 Historical East Hampton Home, 1 Mile to Town!

Guest favourite

Home in Sag Harbor

4.85 out of 5 average rating, 252 reviews

Exclusive Sag Harbor Compound

Home in Sag Harbor

4.81 out of 5 average rating, 112 reviews

Sag Harbor Gem, private, 4 Bedrooms, Pool w Summer

Guest favourite

Home in East Hampton

4.97 out of 5 average rating, 116 reviews

Explore the Water & Woods at a Relaxing Retreat

Guest favourite

Home in Hampton Bays

4.98 out of 5 average rating, 113 reviews

Beach House Feel - newly renovated backyard Oasis

Guest favourite

Home in Manorville

4.99 out of 5 average rating, 205 reviews

Ultimate House with Heated Pool, Hot Tub and Sauna

Weekly house rentals

Guest favourite

Home in Greenport

5.0 out of 5 average rating, 38 reviews

Beachfront Greenport Villa

Guest favourite

Home in Greenport

4.96 out of 5 average rating, 28 reviews

Walk to town, Greenport Village - Harbor Views

Guest favourite

Home in Greenport

4.91 out of 5 average rating, 87 reviews

North Fork Escape - Walk To Village, Beach, Parks

Home in Greenport

5.0 out of 5 average rating, 10 reviews

The Saltbox: Outdoor Dining, Fire Pit, Soaking Tub

Guest favourite

Home in Greenport

5.0 out of 5 average rating, 31 reviews

Historic Stunner in Heart of Village

Guest favourite

Home in Greenport

5.0 out of 5 average rating, 5 reviews

Waterfront Greenport Boathouse

Guest favourite

Home in Greenport

4.94 out of 5 average rating, 87 reviews

Maritime Village Getaway with Backyard

Guest favourite

Home in Greenport

4.96 out of 5 average rating, 25 reviews

Water front 3 bedrooms 2 bathrooms beach house

Private house rentals

Guest favourite

Home in Greenport

5.0 out of 5 average rating, 10 reviews

The Sandy Shack - Coastal Escape

Guest favourite

Home in Greenport

4.96 out of 5 average rating, 26 reviews

Victorian Pearl

Home in East Marion

4.92 out of 5 average rating, 24 reviews

Waterfront Bungalow w/Private Beach on Peconic Bay

Guest favourite

Home in Greenport

4.94 out of 5 average rating, 53 reviews

Greenport Village-sunny 3 bedroom/3 full baths

Guest favourite

Home in Greenport

4.95 out of 5 average rating, 22 reviews

Walk to Beach or to Town …

Guest favourite

Home in Greenport

4.99 out of 5 average rating, 84 reviews

Greenport Village Rental

Guest favourite

Home in Southold

5.0 out of 5 average rating, 14 reviews

Gorgeous home with heated gunnite pool!

Guest favourite

Home in Greenport

4.96 out of 5 average rating, 47 reviews

Greenport Village Getaway

Quick stats about house rentals in Greenport West

Total rentals
150 properties
Rentals with a pool
30 properties have a pool
Pet-friendly rentals
50 properties allow pets
Family-friendly rentals
140 properties are a good fit for families
Total number of reviews
5.6K reviews
Nightly prices starting at
€ 111 before taxes and fees

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