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Results: 145 Rentals

  • Modern, Great sleeping, Walk to town and beach. 2-bedroom condo in Greenport
    From $250 per night (USD)

    VRBO

    Modern, Great sleeping, Walk to town and beach. 2-bedroom condo in Greenport

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    This Greenport condo boasts 2 inviting bedrooms with 1 queen bed and 1 full bed. The cozy living space includes heating ...

    From $250 per night (USD)

    VRBO

    Details
  • Kayak Point: Waterfront, Hot Tub, Viewing Deck
    From $698 per night (USD)

    VRBO

    Kayak Point: Waterfront, Hot Tub, Viewing Deck

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Summary: Discover a tranquil waterfront haven on Southold's Long Creek and Hashamomuck Pond. Nestled among tall oaks on ...

    From $698 per night (USD)

    VRBO

    Details
  • The Village Villa Top Floor
    From $482 per night (USD)

    VRBO

    The Village Villa Top Floor

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Come stay at The Village Villa Top floor with friends or family. Centrally located, walk to everything Greenport has to ...

    From $482 per night (USD)

    VRBO

    Details
  • The Village Villa 1st Floor
    From $556 per night (USD)

    VRBO

    The Village Villa 1st Floor

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    7

    Come stay at The Village Villa First floor with friends or family. Centrally located, walk to everything Greenport has t ...

    From $556 per night (USD)

    VRBO

    Details
  • The Village Villa – Renovated 6-Bedroom Home in the Heart of Greenport Village
    From $1020 per night (USD)

    VRBO

    The Village Villa – Renovated 6-Bedroom Home in the Heart of Greenport Village

    Bedrooms:
    2
    Bathrooms:
    6
    Sleeps:
    13

    Welcome to the Village Villa—a newly renovated, spacious 6-bedroom home nestled right in the heart of Greenport Village. ...

    From $1020 per night (USD)

    VRBO

    Details
  • 4-bedroom house in beautiful Shelter Island with pool, perfect for families
    From $1191 per night (USD)

    VRBO

    4-bedroom house in beautiful Shelter Island with pool, perfect for families

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Discover Your Perfect Retreat on Shelter Island! Welcome to your dream rental home, a stunning 4-bedroom oasis nestled ...

    From $1191 per night (USD)

    VRBO

    Details
  • Sunset Perch: Private Pool, Rooftop Deck
    From $1568 per night (USD)

    VRBO

    Sunset Perch: Private Pool, Rooftop Deck

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    10

    Summary: Experience elevated coastal living in this contemporary and light-filled North Fork retreat set on a private la ...

    From $1568 per night (USD)

    VRBO

    Details
  • Beautiful Waterview Condo on the North Fork of LI
    From $674 per night (USD)

    VRBO

    Beautiful Waterview Condo on the North Fork of LI

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Waterview luxury suite accommodates up to 6 guests with two bedrooms and two bathrooms located on the North Fork of Long ...

    From $674 per night (USD)

    VRBO

    Details
  • Very Large, Comfortable, Victorian 4 Bedroom House + Beach Club
    From $1002 per night (USD)

    VRBO

    Very Large, Comfortable, Victorian 4 Bedroom House + Beach Club

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    6

    Shelter Island Heights 1875 Large Historic Victorian Home For Rent, Sunny 4 bedrooms, 2 baths, Central AC, full dining ...

    From $1002 per night (USD)

    VRBO

    Details
  • Greenport Village Home with Heated Salt Water Pool
    Click For Pricing

    Expedia

    Greenport Village Home with Heated Salt Water Pool

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Discount for taking all of June - August! One of a kind Greenport Village rental! This 1926 renovated 4 bedroom 2.5 bath ...

    Click For Pricing

    Expedia

    Details
  • Coastal Getaway, water views, walk to beach
    From $879 per night (USD)

    VRBO

    Coastal Getaway, water views, walk to beach

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Coastal Vibes: Home with waterviews, short distance from a secluded beach on Pipes Cove overlooking Shelter Island. Bea ...

    From $879 per night (USD)

    VRBO

    Details
  • Resort Style Home- Family Friendly
    From $1200 per night (USD)

    VRBO

    Resort Style Home- Family Friendly

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    6

    Located in beautiful Hay Beach, this home has four bedrooms and three full bathrooms. The main bedroom has a king bed an ...

    From $1200 per night (USD)

    VRBO

    Details
  • Contemporary Colonial home with pristine Peconic bay views, steps to...
    From $1253 per night (USD)

    VRBO

    Contemporary Colonial home with pristine Peconic bay views, steps to...

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    10

    Vineyard Beach House Contemporary Colonial home with pristine Peconic bay views, steps to private beach, Weber grill, f ...

    From $1253 per night (USD)

    VRBO

    Details
  • Relaxation in Greenport
    From $786 per night (USD)

    Expedia

    Relaxation in Greenport

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Renovated house located in the heart of Greenport is perfect for family getaways. Blocks away from Main Street. With ama ...

    From $786 per night (USD)

    Expedia

    Details
  • 2-bedroom in Heart of Greenport Historic District
    Click For Pricing

    VRBO

    2-bedroom in Heart of Greenport Historic District

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Centrally located in the Greenport historic district and just a 5-7 min walk from all the stores, cafes, and restaurants ...

    Click For Pricing

    VRBO

    Details
  • I’ve had the best guests!
    From $514 per night (USD)

    Expedia

    I’ve had the best guests!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Hi everyone: I’d like to sincerely thank all the great guests that stayed at our home, and those of you who viewed the l ...

    From $514 per night (USD)

    Expedia

    Details
  • Sea Pine Cottage
    From $472 per night (USD)

    VRBO

    Sea Pine Cottage

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Nestled in the woods just behind the Pridwin Hotel, walk to Crescent Beach, Perlman Music and Sunset Beach. 1930''s Shel ...

    From $472 per night (USD)

    VRBO

    Details
  • Gorgeous Greenport Beach House right on the Sound! Breathtaking views
    From $1089 per night (USD)

    Expedia

    Gorgeous Greenport Beach House right on the Sound! Breathtaking views

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to Villa Sonore. A gorgeous beachfront home in Greenport located right on the LI Sound. Walk to restaurants and ...

    From $1089 per night (USD)

    Expedia

    Details
  • The Lucky Oyster Est 1886 3 Bd / 2 Ba Historic & Walk to Town
    From $939 per night (USD)

    VRBO

    The Lucky Oyster Est 1886 3 Bd / 2 Ba Historic & Walk to Town

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Located steps from town, this historic gem is perfect for a weekend getaway. With a spacious kitchen, living and dining ...

    From $939 per night (USD)

    VRBO

    Details
  • Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
    From $281 per night (USD)

    Expedia

    Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bar ...

    From $281 per night (USD)

    Expedia

    Details
  • Restored Seaport Village Cottage
    From $686 per night (USD)

    VRBO

    Restored Seaport Village Cottage

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Please Note : Guests must add a message with their reservation request, and kindly indicate who is traveling. Welcome! ...

    From $686 per night (USD)

    VRBO

    Details
  • Sea Breeze Paradise: Beachfront & Panoramic Views
    Click For Pricing

    Expedia

    Sea Breeze Paradise: Beachfront & Panoramic Views

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Summary: Sea Breeze Paradise is a newly renovated home. A paradise for those of you who want to enjoy the sun and fresh ...

    Click For Pricing

    Expedia

    Details
  • Birch Cottage | The Pridwin Hotel and Cottages
    Click For Pricing

    VRBO

    Birch Cottage | The Pridwin Hotel and Cottages

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    A waterfront retreat features a heated outdoor pool, spa, fitness center, and game room, along with on-site dining and l ...

    Click For Pricing

    VRBO

    Details
  • Corner Preferred Room | The Pridwin Hotel and Cottages
    Click For Pricing

    Expedia

    Corner Preferred Room | The Pridwin Hotel and Cottages

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    A waterfront retreat features a heated outdoor pool, spa, fitness center, and game room, along with on-site dining and l ...

    Click For Pricing

    Expedia

    Details
  • Caroline Cottage | The Pridwin Hotel and Cottages
    Click For Pricing

    VRBO

    Caroline Cottage | The Pridwin Hotel and Cottages

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Discover Shelter Island's charm near Crescent Beach and Mashomack Preserve. Enjoy serene beaches, vibrant nature, and lo ...

    Click For Pricing

    VRBO

    Details
  • White Oak Cottage | The Pridwin Hotel and Cottages
    Click For Pricing

    Expedia

    White Oak Cottage | The Pridwin Hotel and Cottages

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    A waterfront retreat features a heated outdoor pool, spa, fitness center, and game room, along with on-site dining and l ...

    Click For Pricing

    Expedia

    Details
  • Hickory Cottage | The Pridwin Hotel and Cottages
    Click For Pricing

    VRBO

    Hickory Cottage | The Pridwin Hotel and Cottages

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    A waterfront retreat features a heated outdoor pool, spa, fitness center, and game room, along with on-site dining and l ...

    Click For Pricing

    VRBO

    Details
  • Craftsman Cottage in Greenport Village
    From $658 per night (USD)

    Expedia

    Craftsman Cottage in Greenport Village

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Come stay in our charming Craftsman cottage, just a short three block walk from all the shops, restaurants, galleries an ...

    From $658 per night (USD)

    Expedia

    Details
  • 5 minute walk to beaches and beautiful downtown Greenport
    From $277 per night (USD)

    VRBO

    5 minute walk to beaches and beautiful downtown Greenport

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Lovely Victorian home with private entrance, porch, and brick patio. Floor to ceiling windows in light filled large bed ...

    From $277 per night (USD)

    VRBO

    Details
  • 4-bed 3.5-bath house with fenced heated pool and hot tub, fire pit, kids swings
    From $457 per night (USD)

    VRBO

    4-bed 3.5-bath house with fenced heated pool and hot tub, fire pit, kids swings

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Family-friendly 2,200 square foot, 4-bedroom, 3.5-bathroom house for rent. The home has all the amenities you need for u ...

    From $457 per night (USD)

    VRBO

    Details
  • Charming Greenport Gem 1, 1 Mile to Ferry!
    From $291 per night (USD)

    VRBO

    Charming Greenport Gem 1, 1 Mile to Ferry!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Travel to the North Fork of Long Island for a much-needed getaway and experience both modern luxury and historic desire ...

    From $291 per night (USD)

    VRBO

    Details
  • Entire, new, roomy,  village beach house close to beach, park, and town center
    From $666 per night (USD)

    Expedia

    Entire, new, roomy, village beach house close to beach, park, and town center

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Welcome to our most lovely Greenport Beach Home.....800 feet to sixth street beach and playground. A true beach getaway, ...

    From $666 per night (USD)

    Expedia

    Details
  • Idyllic North Fork hideaway! Quiet 3 Bedroom cape in East Marion
    From $682 per night (USD)

    VRBO

    Idyllic North Fork hideaway! Quiet 3 Bedroom cape in East Marion

    Bedrooms:
    1
    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 $682 per night (USD)

    VRBO

    Details
  • Beautifully renovated 2 Bedroom, 1st Floor apt -Greenport Village, Walk to town!
    From $540 per night (USD)

    Expedia

    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 $540 per night (USD)

    Expedia

    Details
  • Lagoon Lodge North Fork, Charming 3Br, Waterfront
    From $413 per night (USD)

    VRBO

    Lagoon Lodge North Fork, Charming 3Br, Waterfront

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Summary: Lagoon Lodge is a charming waterfront home with 3 bedrooms and 2 bathrooms, featuring central air and high-spee ...

    From $413 per night (USD)

    VRBO

    Details
  • Exquisite Waterfront Townhome in Greenport with Pool and Boat Slip. Walk to all!
    From $449 per night (USD)

    VRBO

    Exquisite Waterfront Townhome in Greenport with Pool and Boat Slip. Walk to all!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Beautifully appointed townhouse in coveted Stirling Cove Condominiums. Enter a light filled room with magnificent views ...

    From $449 per night (USD)

    VRBO

    Details
  • Unique waterfront home w/ stunning views, boat slip, walk to historic Greenport
    From $621 per night (USD)

    VRBO

    Unique waterfront home w/ stunning views, boat slip, walk to historic Greenport

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    North Fork living doesn’t get better than this. Enter to stunning waterfront views from every corner of this unique, lig ...

    From $621 per night (USD)

    VRBO

    Details
  • Water front beach house w/ private beach with 3 bedrooms/2 bathrooms/Large Deck
    From $887 per night (USD)

    Expedia

    Water front beach house w/ private beach with 3 bedrooms/2 bathrooms/Large Deck

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    In the picturesque seaside village of Greenport, this ocean-view three-bedroom retreat provides a peaceful and refreshin ...

    From $887 per night (USD)

    Expedia

    Details
  • WALK TO TOWN, BEACH, JITNEY, & FISHING---No Car Necessary!
    From $528 per night (USD)

    VRBO

    WALK TO TOWN, BEACH, JITNEY, & FISHING---No Car Necessary!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Charming, in-town neighborhood. 10-minute walk to shops, beaches and fishing pier, the Hampton Jitney, LIRR and the Shel ...

    From $528 per night (USD)

    VRBO

    Details
  • Walk to private bay beach, close to Greenport, wineries, golf! Premier Host home
    From $594 per night (USD)

    Expedia

    Walk to private bay beach, close to Greenport, wineries, golf! Premier Host home

    Bedrooms:
    2
    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 $594 per night (USD)

    Expedia

    Details
  • Family and Friends in Historic Greenport
    From $447 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 $447 per night (USD)

    VRBO

    Details
  • Lovely North Fork Sea Captain's Home
    From $895 per night (USD)

    VRBO

    Lovely North Fork Sea Captain's Home

    Bedrooms:
    2
    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 $895 per night (USD)

    VRBO

    Details
  • Heavenly Craftsman  Just minutes to beaches, vineyards, ferries and Greenport!
    From $514 per night (USD)

    VRBO

    Heavenly Craftsman Just minutes to beaches, vineyards, ferries and Greenport!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Rental Permit 1048 Perfect and original Craftsman Arts and Crafts style house. This is the loveliest historic house l ...

    From $514 per night (USD)

    VRBO

    Details
  • Aqua Vista
    From $160 per night (USD)

    Expedia

    Aqua Vista

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bar ...

    From $160 per night (USD)

    Expedia

    Details
  • The SandPiper
    From $160 per night (USD)

    VRBO

    The SandPiper

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bar ...

    From $160 per night (USD)

    VRBO

    Details