Greenport West Rentals
- From $368 per night (USD)
VRBO
Lavender Fields Retreat: Nearby the Beach & Farms
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Situated on the North Fork of Long Island in the hamlet of East Marion, New York. This charming Lavender Fields Retreat ...
From $368 per night (USD)VRBO
- From $1050 per night (USD)
VRBO
Beautiful Renovated Beachfront Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
High on a bluff overlooking the Sound, this amazing Sound front home has been completely renovated with a chef's gourmet ...
From $1050 per night (USD)VRBO
- From $2250 per night (USD)
VRBO
Jewel of the North Fork -Bachelorette Paradise-Must Rent Full Weeks in Summer
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 12
This extraordinarily beautiful, one-of-a-kind beach house is located on 4+ acres with a private beach spanning 1,100' on ...
From $2250 per night (USD)VRBO
- From $489 per night (USD)
VRBO
Greenport Waterfront Cottage w\/Private Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located in the historic and centuries-old town of Greenport Village with its quiet streets, serious dining options and ...
From $489 per night (USD)VRBO
- From $1333 per night (USD)
VRBO
Beach and waterfront Estate - One of a Kind Vacation House
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Same location I have two 2 cottages that sleep 4 each . See VRBO search bar [Where To] with the Listing ID 173361 and th ...
From $1333 per night (USD)VRBO
- From $1236 per night (USD)
VRBO
Tranquil, Beachfront Getaway with Dock, Fabulous Sunset Views!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This Shelter Island beach house has all the necessary ingredients for a fabulous year-round getaway. Located on a shy ac ...
From $1236 per night (USD)VRBO
- From $810 per night (USD)
VRBO
Renovated Waterfront Cottage With Spectacular Views And Private Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This home sits on the edge of a bluff with unobstructed views of the water and a secluded cove with direct access to a b ...
From $810 per night (USD)VRBO
- Click For Pricing
Expedia
Refurbished North Fork cottage with large yard, patio, grill, AC & washer\/dryer
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
North Fork Nest Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
Click For PricingExpedia
- From $675 per night (USD)
VRBO
Lovely North Fork Sea Captain's Home
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Town of Southold Rental Permit 0605 The Sea Captain's Home is a sprawling, well-preserved, 4-bedroom-plus Italianate V ...
From $675 per night (USD)VRBO
- From $246 per night (USD)
VRBO
Unspoiled North Fork Charm, walk to bay & sound beaches, minutes to Greenport
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Vintage North Fork cottage tucked away under the trees. Enjoy cool breezes through the many spacious windows. An easy ca ...
From $246 per night (USD)VRBO
- From $1500 per night (USD)
VRBO
Beautiful waterfront house in Southold
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Beautiful Waterfront Home With Stunning Views of Hashamomuck Pond. Escape from it all for a memorable family vacation in ...
From $1500 per night (USD)VRBO
- From $592 per night (USD)
Expedia
Brand new 2 bedroom, Greenport Village, walk to town Marina Views!!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Luxury 2 bedroom, first floor apartment located across the street from Townsend Manor Marina in the heart of Greenport V ...
From $592 per night (USD)Expedia
- From $1100 per night (USD)
VRBO
Bohemian Old Life Saving Station with Beach & Pool
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 13
ONLY 1 WEEK RENTALS FROM MID JUNE TO MID SEPTEMBER RENTALS ARE FROM FRIDAY TO FRIDAY AVAILABILITY FOR JULY & AUGUST IS ...
From $1100 per night (USD)VRBO
- From $400 per night (USD)
VRBO
Private & Spacious Five Room Suite..Steps To Bay Beach and walk to Village.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
1896 Restored Victorian located within steps to a lovely Bay Beach. Village restaurants, shops, NYC Hampton Jitney Expre ...
From $400 per night (USD)VRBO
- From $822 per night (USD)
VRBO
Spacious Modern on wooded lot - 5 min from beach!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Newly renovated, spacious, 4 bedroom, 3.5 bath house on 1.25 acres in the Hay Beach neighborhood of Shelter Island overl ...
From $822 per night (USD)VRBO
- From $375 per night (USD)
VRBO
First Floor 1905 Victorian home in the heart of Greenport Village
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Home has a full kitchen and a washer/dryer. There are two bedrooms with queen size beds plus a Murphy double bed. One ba ...
From $375 per night (USD)VRBO
- From $510 per night (USD)
VRBO
1820 Whaling Captain's Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Set in the historic section of Greenport village, the Captain’s House, built in 1820, is an elegant and charming 3 bedro ...
From $510 per night (USD)VRBO
- From $941 per night (USD)
VRBO
Unique Southold waterfront luxury home with heated pool on Long Creek
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
We bought our wonderful house five years ago and have made many important renovations. The newest is a hybird bocce cour ...
From $941 per night (USD)VRBO
- From $1113 per night (USD)
VRBO
POOL + Private Beach near Greenport!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 11
Make yourself at home in this 4 bedroom / 3 full bathroom modern ranch featuring: * chef's eat-in kitchen w/ 2 ovens, lu ...
From $1113 per night (USD)VRBO
- Click For Pricing
Expedia
🌟 Walk to the village ❤ of Greenport
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Stay in our Cozy Greenport home, in one of the most central and convenient locations in Greenport Village! *Amazing Wint ...
Click For PricingExpedia
- From $285 per night (USD)
VRBO
Quaint East Marion Cottage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Our quaint cottage is the perfect place to enjoy all that the North Fork has to offer! Walk to the end of the block to t ...
From $285 per night (USD)VRBO
- From $400 per night (USD)
VRBO
Charming Northfork Getaway
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Newly renovated and charming home in the NorthFork, a short walk to the village of Greenport, vineyards, and the breatht ...
From $400 per night (USD)VRBO
- From $650 per night (USD)
VRBO
Storybook Beautiful 3-Bedroom Cape
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Rental Permit # 0573 This is a newly renovated 3 bedroom ( one bedroom is in the loft) cottage in the beautiful histori ...
From $650 per night (USD)VRBO
- From $870 per night (USD)
VRBO
Beautiful Secluded Family Home on Shelter Island.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This is a magical house. It is surrounded by woods and a pond. The only sounds you hear are the birds and other animals, ...
From $870 per night (USD)VRBO
- From $534 per night (USD)
VRBO
Charming historic house on Sterling Harbor, waterviews, walk to village
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 5
Tucked away along Sterling Harbor in Greenport’s Historic District -- on the village's most desired street -- sits this ...
From $534 per night (USD)VRBO
- From $339 per night (USD)
VRBO
Architect Designed Home in Waterfront Village
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Designed and built in 2003, this cozy house has water views of Peconic Bay, enormous glass skylights, fully equipped kit ...
From $339 per night (USD)VRBO
- From $539 per night (USD)
VRBO
Waterfront Bungalow w\/ Private Beach on Peconic Bay
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Relax on your private Beach, hit the Vineyard Trail, stroll around Downtown Greenport or ferry to Shelter Island, friend ...
From $539 per night (USD)VRBO
- From $389 per night (USD)
VRBO
Family and Friends in Historic Greenport
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Our house is an historic Dutch colonial, both cozy and spacious, with warm wood trim and wood floors throughout. The 20 ...
From $389 per night (USD)VRBO
- From $420 per night (USD)
VRBO
'The Gate House' on Beach front Estate Walk to Village
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Located on a family-owned waterfront estate, The Gate House, a cozy 2-story, 2-bedroom cottage, is only steps away from ...
From $420 per night (USD)VRBO
- From $619 per night (USD)
Expedia
American Beech in Greenport - Two-Bedroom Apartment 8
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The 19th-century historic and centrally located Stirling Square in Greenport Village has been reimagined into the modern ...
From $619 per night (USD)Expedia
- From $279 per night (USD)
VRBO
American Beech in Greenport - Deluxe King Suite 11
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The 19th-century historic and centrally located Stirling Square in Greenport Village has been reimagined into the modern ...
From $279 per night (USD)VRBO
- From $259 per night (USD)
Expedia
American Beech - Deluxe King 5
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The 19th-century historic and centrally located Stirling Square in Greenport Village has been reimagined into the modern ...
From $259 per night (USD)Expedia
- From $239 per night (USD)
VRBO
American Beech in Greenport - Petite King Room 7
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The 19th-century historic and centrally located Stirling Square in Greenport Village has been reimagined into the modern ...
From $239 per night (USD)VRBO
- From $389 per night (USD)
Expedia
American Beech in Greenport - Deluxe King Suite 12
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The 19th-century historic and centrally located Stirling Square in Greenport Village has been reimagined into the modern ...
From $389 per night (USD)Expedia
- From $279 per night (USD)
VRBO
American Beech in Greenport - Deluxe King 4
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The 19th-century historic and centrally located Stirling Square in Greenport Village has been reimagined into the modern ...
From $279 per night (USD)VRBO
- From $349 per night (USD)
Expedia
American Beech in Greenport NY - King Suite 1
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The 19th-century historic and centrally located Stirling Square in Greenport Village has been reimagined into the modern ...
From $349 per night (USD)Expedia
- From $619 per night (USD)
VRBO
American Beech - Luxury 2 Bedroom Apartment 10
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The 19th-century historic and centrally located Stirling Square in Greenport Village has been reimagined into the modern ...
From $619 per night (USD)VRBO
- From $299 per night (USD)
Expedia
American Beech - Deluxe King Suite 14
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The 19th-century historic and centrally located Stirling Square in Greenport Village has been reimagined into the modern ...
From $299 per night (USD)Expedia
- From $259 per night (USD)
VRBO
American Beech - King Suite 2
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The 19th-century historic and centrally located Stirling Square in Greenport Village has been reimagined into the modern ...
From $259 per night (USD)VRBO
- From $259 per night (USD)
Expedia
American Beech in Greenport - Deluxe King 6
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The 19th-century historic and centrally located Stirling Square in Greenport Village has been reimagined into the modern ...
From $259 per night (USD)Expedia
- From $259 per night (USD)
VRBO
American Beech in Greenport - King Suite 3
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The 19th-century historic and centrally located Stirling Square in Greenport Village has been reimagined into the modern ...
From $259 per night (USD)VRBO
- From $279 per night (USD)
VRBO
Historic 1830s Greenport Home
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
2024 AVAILABILITY! Looking to escape the city for a couple of weeks or even a month? The house is well set up for wor ...
From $279 per night (USD)VRBO
- From $667 per night (USD)
VRBO
90 feet of private waterfront w beach, new renovation, panoramic views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Spacious and Luxurious 3 bedroom; brand new construction with 120 feet of waterfront and spectacular sunset views • 2 l ...
From $667 per night (USD)VRBO
- From $276 per night (USD)
Expedia
Quaint DT Greenport Apt - 2 Mi to Shelter Island!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Surround yourself with seaside charm at this Greenport vacation rental. Perfect for couples and solo travelers, this 1-b ...
From $276 per night (USD)Expedia
- From $294 per night (USD)
VRBO
Bright Apartment - 1\/2 Mi to Greenport Harbor!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Combine peace and quiet with bustling downtown action when you book this charming Greenport vacation rental! The 1-bedro ...
From $294 per night (USD)VRBO
- From $975 per night (USD)
VRBO
NEW VICTORIAN GEM IN GREENPORT
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
Newly renovated Victorian house in Greenport. 5 queen bedrooms with private full baths, spacious, super clean and meticu ...
From $975 per night (USD)VRBO
- From $1350 per night (USD)
VRBO
Greenport Magical Gem - Beautiful Backyard And Pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
The uniqueness of this wonderful home is the backyard which is lavishly landscaped with both beautiful flowers and lush ...
From $1350 per night (USD)VRBO
- From $400 per night (USD)
VRBO
Gorgeous lakefront retreat
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Stunning 3 bedroom ranch style home on the lake in East Marion. Sleeps 6 in comfort. Come and watch the Ospreys fish fro ...
From $400 per night (USD)VRBO
- From $700 per night (USD)
VRBO
Renovated and Spacious Summer Home with Water View on Picturesque Island.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Steps from the beach, this beach house is the perfect destination to enjoy beautiful Shelter Island. Recently renovated ...
From $700 per night (USD)VRBO
- Click For Pricing
VRBO
Greenport Village - Spacious 3-Bedroom, 3-Bath Bungalow
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Newly renovated 1800 square feet bungalow home in the heart of Greenport Village (~12-minute walk to restaurants in town ...
Click For PricingVRBO
- From $500 per night (USD)
VRBO
Cottage on Beach front Estate .Walk to Village
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Charming 2-bedroom cottage located on a family-owned waterfront estate that was converted from a circa 1920s chicken coo ...
From $500 per night (USD)VRBO
- From $850 per night (USD)
VRBO
Renovated 4-Bedroom House with Heated Pool & Private Beach Access
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Incredible beach house just minutes from Greenport! This freshly renovated home is a dream family vacation spot. It's ...
From $850 per night (USD)VRBO
- From $471 per night (USD)
VRBO
Seaside seclusion, salt water sanctuary!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Greenport is a charming seaside town with historic architecture with awesome restaurants and plenty to see and do! Trav ...
From $471 per night (USD)VRBO
- From $1225 per night (USD)
VRBO
Dream Beach House on the North Fork: Waterfront, Private Beach + Stunning Views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
One of the nicest spots on the North Fork (that's a quote from a knowledgeable local!), beautifully designer-renovated b ...
From $1225 per night (USD)VRBO
- From $995 per night (USD)
VRBO
Elegant Victorian in the Heart of Greenport
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 13
Winter Harbor House is a stylish Victorian walking distance from the best restaurants, bars and beaches in Greenport Vil ...
From $995 per night (USD)VRBO
- Click For Pricing
VRBO
Beautiful brand-new house steps from water!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Gorgeous brand new, large house overlooking Hashamomack Pond. Steps to boat ramp, and minutes to vineyards, nature prese ...
Click For PricingVRBO
- From $1154 per night (USD)
VRBO
Beat the Heat @ this Shelter Island Gem!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beat the heat in this fabulous summer retreat on laid back Shelter Island. Restaurants, antiquing, wineries, hiking, bi ...
From $1154 per night (USD)VRBO
- From $604 per night (USD)
Expedia
Waterfront, private beach, ready for adventure, light & bright!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Set on a magical one-acre promontory, jutting into beautiful Long Creek with spectacular water views from every room, th ...
From $604 per night (USD)Expedia
- Click For Pricing
VRBO
Perfect family getaway on beautiful Shelter Island!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This 1870s farmhouse is conveniently located near shops, golf and beautiful Crescent Beach. They are three bedrooms, tw ...
Click For PricingVRBO
- From $392 per night (USD)
Expedia
Newly built ranch, beautifully landscaped with pool, large yard, patio,...
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Greenport Getaway Newly built ranch, beautifully landscaped with pool, large yard, patio, fire pit, ample seating, minu ...
From $392 per night (USD)Expedia
- From $600 per night (USD)
VRBO
Greenport, North Fork, Beach, Designer Chic, Vineyard Views, Hamptons luxury
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
Charming, private, sun filled 3 bedroom Designer country home with fireplace, spacious living area including den/library ...
From $600 per night (USD)VRBO
- From $599 per night (USD)
Expedia
Walk to private bay beach, close to Greenport, wineries, golf! Premier Host home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Our home has been a family retreat for over 20 years, and has been completely refreshed in 2022. Interior painted, new f ...
From $599 per night (USD)Expedia
- From $533 per night (USD)
VRBO
Lagoon Lodge: North Fork,Charming 3Br, Waterfront, near Greenport, WIFI
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Lagoon Lodge is a charming waterfront home with 3 bedrooms, and 2 bathrooms, and has central air and high-speed internet ...
From $533 per night (USD)VRBO
- From $425 per night (USD)
VRBO
Beautifully decorated water view resort condo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Cliffside Resort is located on a bluff overlooking the Long Island sound with beautiful water vistas. The resort has an ...
From $425 per night (USD)VRBO
- From $548 per night (USD)
VRBO
Shelter Bay Cove Waterfront, North Fork , Hamptons ,Long Island
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
World class views of water and sunsets are the signature features of this charming, 3 bedroom house with 90 feet of wate ...
From $548 per night (USD)VRBO
- From $1349 per night (USD)
VRBO
Classic Waterview Victorian Summer Cottage in Park-Like-Setting
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 6
Beautiful turn-of-the century Victorian Summer Beautiful turn of the century home located on Rainbow Park with breatht ...
From $1349 per night (USD)VRBO
- From $671 per night (USD)
VRBO
Idyllic North Fork hideaway! Quiet 3 Bedroom cape in East Marion
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Relax, rejuvenate and recharge in this updated North Fork gem with new kitchen, outdoor deck, screened in porch and larg ...
From $671 per night (USD)VRBO
- Click For Pricing
VRBO
Waterfront Oasis on the North Fork
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Our creekside home is one of the best places to spend a summer on the North Fork of Long Island. Located steps from a sa ...
Click For PricingVRBO
- From $2000 per night (USD)
VRBO
One Of A Kind, Resort- Like Waterfront Cottage In Wine Country
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
LI Sound Waterfront Cottage with 2 Bedrooms and 1 Bathroom. Completely Renovated and Modern Living Space with Open Layou ...
From $2000 per night (USD)VRBO
- From $1000 per night (USD)
Expedia
Picture Perfect Greenport Cottage
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Well appointed cottage for all seasons. Picture perfect privet lined outdoor living space with sofas, dining area, fire ...
From $1000 per night (USD)Expedia
- From $500 per night (USD)
VRBO
Beautifully renovated 2 Bedroom, 1st Floor apt -Greenport Village, Walk to town!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy this beautifully renovated first floor “Captains House” apartment in the heart of Greenport Village. Harbor Views ...
From $500 per night (USD)VRBO
- From $593 per night (USD)
Expedia
House by the Bay with Large In-ground Pool, Steps from Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Have a perfect vacation in our pristine two-story farmhouse style house. There are three bedrooms and two full baths. On ...
From $593 per night (USD)Expedia
- From $1121 per night (USD)
VRBO
Relax in this light-filled home, steps from the beach and a short walk to town!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
The perfect getaway. Within walking distance to beach, town, Jitney, LIRR and ferries to the South Fork. This quiet and ...
From $1121 per night (USD)VRBO
- From $575 per night (USD)
Expedia
North Fork Waterview Retreat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Experience serene living on Long Island's highly sought after North Fork. This home boasts water views of Peconic Bay a ...
From $575 per night (USD)Expedia
- From $700 per night (USD)
VRBO
Antique house, Private & Peaceful Oasis
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Newly restored antique home, 3 bedrooms, 1.5 baths with outdoor shower surrounded by manicured lawn & bucolic grounds. ...
From $700 per night (USD)VRBO
- Click For Pricing
VRBO
Perfect Getaway Apartment For Couples or Single Travelers
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Newly renovated apartment minutes away from the beach! This second floor space comes fully furnished with a full size be ...
Click For PricingVRBO
- Click For Pricing
VRBO
Chic, Historic fully renovated Greenport Home
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 6
14 day minimum but can rent up to 8 weeks. !! No less than 2 week rentals. Landmark, 3+ + br Greenport home, circa 168 ...
Click For PricingVRBO
- From $293 per night (USD)
VRBO
Beachy Cottage by the Bay
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Our family cottage has provided joy and memories for decades, and after fixing it up over the past year we are excited t ...
From $293 per night (USD)VRBO
- From $425 per night (USD)
VRBO
Located in the heart of wine country
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Beautiful grand victorian in mint condition. Spacious 4 bedroom home with original woodwork and amazing architectural de ...
From $425 per night (USD)VRBO
- From $888 per night (USD)
VRBO
Scandinavian modern style meets the North Fork. NEW 18 x 40 gunite pool June 1.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Newly remodeled, clean and peaceful North Fork beach house. Minutes from Greenport and Orient. 18 x 40 gunite heated po ...
From $888 per night (USD)VRBO
- Click For Pricing
VRBO
Fishermans Cottage near Crescent Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This 1920's original is nestled in a land reserve just off Crescent Beach. Enchanting and quiet, this property is in a u ...
Click For PricingVRBO
- From $2710 per night (USD)
Expedia
Elevated Views Over Shelter Island Sound, Wraparound Deck Overlooking...
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
Sunset Beach Elevated Views Over Shelter Island Sound, Wraparound Deck Overlooking Beach, High-End Amenities, Access to ...
From $2710 per night (USD)Expedia
- From $1003 per night (USD)
VRBO
Newly Renovated Summer Retreat, Heated Pool, Walk to Beach, Designer Furnishings
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
*30 day minimum rental* Newly renovated modern farmhouse on a spacious property with a large heated saltwater pool and p ...
From $1003 per night (USD)VRBO
- From $575 per night (USD)
VRBO
Family friendly home near beach with wonderful deck!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
You can walk to the beach from this attractive home that comfortably sleeps 7. Enjoy cocktails and outdoor dining on th ...
From $575 per night (USD)VRBO
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VRBO
Shingled Chic & Modern Light & Bright
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This unique remodeled 1930's home is tastefully decorated with modern and vintage touches. Central air and heat. Enjoy t ...
Click For PricingVRBO
- From $379 per night (USD)
VRBO
Spacious apartment, 3 blocks to downtown and steps to fishing pier.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The Property Charming and newly updated second floor apartment, less than a 5 minute walk to downtown. Enjoy our incredi ...
From $379 per night (USD)VRBO
- From $450 per night (USD)
VRBO
Cleves Point Estates Home, Private sandy beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This beautiful house is located in a private beach community. An 8 minute walk brings you to a private beach with view ...
From $450 per night (USD)VRBO
- From $970 per night (USD)
Expedia
Historic Luxurious Captains Home- Greenport Village, wineries,golf, beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
NO EXTRA FEES FOR CLEANING, EXTRA GUESTS & AMENITIES! Relax in one of America's most beautiful seaside villages, histo ...
From $970 per night (USD)Expedia
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VRBO
NOT FOR RENT
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to the Victorian Seasons One bedroom Carriage House Duplex. Nestled between wildlife preserves and protected lan ...
Click For PricingVRBO
- From $600 per night (USD)
Expedia
Maritime Village House Walk or Bike to All
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful updated historic home in the village of Greenport. Central AC, newly renovated kitchens and bathrooms, large f ...
From $600 per night (USD)Expedia
- From $634 per night (USD)
VRBO
Shelter Island high on the hill ! Acre + 3 bed 2 bath spacious, water view.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This beautiful home has spectacular views from all windows. It is spotless, upscale with attention to details. Such as ...
From $634 per night (USD)VRBO
- From $1200 per night (USD)
VRBO
Picturesque Views Of Gardiners Bay \/ Shelter Island With Heated Waterfront Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
The charming 3 bedroom, 2 bath house is located in East Marion; a (literal) stone's throw from a private sand beach, a f ...
From $1200 per night (USD)VRBO
- From $403 per night (USD)
VRBO
Beautiful, newly-remodeled home w\/ a gas fireplace, patio, & firepit - dogs OK
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Greenport Village Vacationer's Delight Our calendar is updated in real-time & our nightly rates are accurately displaye ...
From $403 per night (USD)VRBO
- From $1500 per night (USD)
Expedia
TRANQUIL RESORT STYLE RETREAT WITH LUXURY GUNITE POOL 2 MIN FROM SANDY BEACHES
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This newly renovated sun-drenched Shelter Island retreat with an exquisite 21'x42' Gunite, wifi-enabled luxury heated po ...
From $1500 per night (USD)Expedia
- From $1890 per night (USD)
VRBO
1905 North Fork Farm restored
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
This newly renovated 1905 North Fork farmhouse comes with lots of light, clean lines, and a brand new heated pool. A ne ...
From $1890 per night (USD)VRBO
- From $604 per night (USD)
VRBO
Exquisite Waterfront Townhome in Greenport with Pool and Boat Slip. Walk to all!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Beautifully appointed townhouse in coveted Stirling Cove Condominiums. Enter a light filled room with magnificent views ...
From $604 per night (USD)VRBO
- From $425 per night (USD)
VRBO
Renovated apt with farmhouse vibe
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
newly renovated 3 bedroom in the heart of Greenport. This spacious and sunny apt on the first floor has an open floor pl ...
From $425 per night (USD)VRBO
- From $900 per night (USD)
Expedia
Enchanting home with beautiful bay views in the heart of Greenport Village
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Enchanted home with beautiful bay views. This house has it all. Modern updates with old-world charm. Gorgeous chefs ki ...
From $900 per night (USD)Expedia
- From $471 per night (USD)
VRBO
Private Pebble Beach Community with Tennis next to Island End Public Golf Course
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Tucked away between farmland and Long Island Sound in Pebble Beach Farms, East Marion, this very clean, single story ran ...
From $471 per night (USD)VRBO
- From $450 per night (USD)
VRBO
Peaceful Shelter Island sanctuary with heated gunite saltwater pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This property is extremely quiet and peaceful sitting on almost an acre of beautifully landscaped gardens and backing on ...
From $450 per night (USD)VRBO