Vacation Rentals in Greenport, NY

221 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • stayz
  • expedia
  • hotelscom
  • tripadvisor
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelopia
Greenport, NY holiday rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

221 Holiday rentals and Airbnb in Greenport, NY

Guests’ Top-Picked Family Holiday Rentals in Greenport, NY, United States

Give the kids instant backyard beach fun and plenty of room to unwind at spacious family holiday rentals in Greenport, NY, United States.

Greenport Beachfront Home | Private Beach & Sunset - Greenport, NY
No reviews

Greenport Beachfront Home | Private Beach & Sunset

apartment, Southold
This family-friendly apartment in Southold offers direct private beachfront access, perfect for swimming, fishing, paddle boarding, and kayaking, with unobstructed views for enjoying daily sunsets.
This spacious accommodation sleeps up to nine guests and features a fully equipped kitchen, air conditioning, a garden, a fitness centre, parking, and an expansive dual-sided deck with a firepit and BBQ area for coastal relaxation.
Beachfront Greenport Villa - Greenport, NY
9.8 13 reviews

Beachfront Greenport Villa

apartment, Southold
This beachfront house is situated in Greenport, a short distance from the Soundview, offering easy access to restaurants, bars, and the North Fork's wineries, breweries, and farms.
The property, which can accommodate up to eight guests, boasts a private enclosed porch and back deck, providing stunning views of the Long Island Sound, and includes amenities such as paddle boards, bicycles, and beach chairs.
Beautiful 2 Bedroom, 2 Bath Greenport Village Loft - Greenport, NY
9.9 39 reviews

Beautiful 2 Bedroom, 2 Bath Greenport Village Loft

apartment, Greenport
This Greenport apartment is a 5-minute walk from the bustling Front Street and Main Street, where you'll find shops, restaurants, and bars, and is also located across from a park and playground. The apartment has excellent user, location, and cleanliness ratings.
The apartment has two bedrooms and two bathrooms, accommodating up to five guests. Enjoy the private outdoor dining on the rear deck, relax on the covered front porch, or unwind in the private yard with a BBQ, fire pit, Adirondack chairs, and lounge areas.
Northfork Townhouse Walk To All - Greenport, NY
10 7 reviews

Northfork Townhouse Walk To All

apartment, Greenport
This three-bedroom house is situated in central Greenport, just under a kilometre from the Greenport Farmers' Market, the Railroad Museum of Long Island, and the Camera Obscura.
The property is ideal for families or groups of up to six, with a fully equipped kitchen, a garden, and parking available.

Top-Rated Holiday Rentals with a Pool in Greenport, NY, United States

Spend your days alternating between the sun loungers and the water at holiday rentals with a pool in Greenport, NY, United States.

Beautiful Condo On The Long Island Sound In A Resort - Greenport, NY
9.7 149 reviews

Beautiful Condo On The Long Island Sound In A Resort

apartment, Greenport
This two-bedroom apartment is situated on Long Island Sound in Greenport, a short distance from the town centre and local wineries, offering a peaceful and scenic setting. The property has consistently received excellent ratings for its cleanliness, location, and overall user experience.
This self-catering accommodation comfortably sleeps up to six guests and features a spacious living room with a sofa bed, two private bathrooms, and a fully equipped kitchen. Guests can enjoy access to a range of amenities, including a heated swimming pool, a clubhouse, barbecue facilities, and a garden, as well as activities such as morning yoga and outdoor movie screenings.
Stylish Getaway In Greenport - Greenport, NY
9.6 42 reviews

Stylish Getaway In Greenport

apartment, Greenport
This Greenport house, situated 0.5 kilometres from Greenport Village centre, offers easy access to local shops, restaurants, beaches, and marinas.
Sleeping six guests, this fully renovated three-bedroom, three-bathroom property boasts a large eat-in kitchen, expansive living room, and private garden, plus a swimming pool and parking.
Cliffside Resort Condominiums - Greenport, NY
9.0 283 reviews

Cliffside Resort Condominiums

resort, Greenport
Cliffside Resort Condominiums, a Greenport aparthotel, offers direct beach access and is situated within 4.8 kilometres of Kontokosta Winery, 67 Steps Beach, and Norman E. Klipp Marine Park.
This resort provides pet-friendly apartments with air conditioning, Wi-Fi, swimming pool, garden, parking, and furnished balconies, featuring fully equipped kitchenettes, two bathrooms, and a seating area, with barbecue grills and a picnic area available for guests.
Waterfront Condo C204 At The Cliffside Resort With Amazing Water & Sunset Views - Greenport, NY
9.9 197 reviews

Waterfront Condo C204 At The Cliffside Resort With Amazing Water & Sunset Views

apartment, Greenport
This Greenport apartment is located in the Cliffside Resort Condominiums on the North Fork of Long Island, just a short walk from the beach. The apartment has excellent user, location, and cleanliness ratings.
The apartment, which is 65 square metres in size, has two bedrooms, two bathrooms, and can accommodate up to six guests. It offers a range of amenities including a private balcony and deck, a well-equipped kitchenette, and access to a private beach, swimming pool, and spa.

Frequently asked questions about holiday rentals in Greenport, NY

  • Which walking or cycling routes are the best in Greenport, NY?

    For a scenic walk or bike ride, try the Greenport Waterfront Trail along the harbor. It's a lovely way to enjoy the views and maybe stop for a bite at one of the restaurants along the way. You can also cycle along the Soundview Greenbelt Trail, which offers a nice mix of waterfront and woodland scenery.
  • What are the best Airbnb and holiday rentals in Greenport, NY?

    Aqua Vista, The Cliffside Resort Condominiums and Amazing Greenport Village Apartment In Center are among the best Airbnb and holiday rentals in Greenport, NY.

  • What sports or outdoor activites can visitors enjoy in and around Greenport, NY?

    Greenport is a great place for outdoor activities. You can go swimming, kayaking, or paddleboarding in the Peconic Bay. There are also plenty of opportunities for fishing, boating, and hiking in the surrounding area. The Orient Point State Park is a great spot for a picnic and a walk along the beach.
  • What are the most popular Airbnbs in Greenport, NY?

    Among the Airbnbs in Greenport, NY, Aqua Vista, Amazing Greenport Village Apartment In Center and Squire Chase House are the most popular ones.

  • What other towns or cities can be easily accessed from Greenport, NY?

    From Greenport, you can easily reach other charming towns on the North Fork of Long Island, such as Shelter Island, Mattituck, Cutchogue, Southold, and Orient. It's a beautiful drive through the countryside.
  • What are the best holiday rentals with a pool in Greenport, NY?

    The Cliffside Resort Condominiums, Greenport Beach House and Sound Front Condominium are the best holiday rentals with a pool in Greenport, NY.

  • What amenities are commonly available in vacation rentals in Greenport, NY?

    Vacation rentals in Greenport often come with amenities like Wi-Fi, air conditioning, laundry facilities, and parking. Many also have kitchens, so you can cook your own meals. Some might even have a backyard, a patio, or a hot tub.
  • What are the best rentals for families and kids in Greenport, NY?

  • What time of year is best to rent a vacation rental Greenport, NY?

    The best time to visit Greenport really depends on your preferences. The summer months (June to August) are the busiest and warmest, with plenty of sunshine and outdoor activities. Spring and autumn offer milder weather and fewer crowds, while winter can be quiet and peaceful.
  • What are the best rentals or Airbnbs with a jacuzzi in Greenport, NY?

Popular destinations

Top-Rated Holiday Rentals with a Balcony in Greenport, NY, United States

Wake up to the soothing sights and sounds of blue ocean waters directly from your private rental balcony in Greenport, NY, United States.

North Fork Resort - Greenport, NY
9.6 1 review

North Fork Resort

resort, Greenport
Resort listing with an excellent rating of 96% based on 1 reviews. You will be based in Greenport.
Services and facilities include a garden, free parking and a swimming pool. This resort in Greenport is ideal for families.
Gorgeous 5 Bdrm Home With Beautiful Bay Views In The Heart Of Greenport Village - Greenport, NY
10 22 reviews

Gorgeous 5 Bdrm Home With Beautiful Bay Views In The Heart Of Greenport Village

apartment, Greenport
This charming house is located just 1 kilometre from Greenport's vibrant waterfront, with easy access to the Farmers' Market, Camera Obscura, and the Maritime Museum. It has received excellent ratings from previous guests, making it a popular choice for travellers.
The property has 4 bedrooms, comfortably accommodating up to 10 guests. Guests can enjoy the spacious garden, relax on the terrace, and make use of the modern kitchen, complete with a dishwasher, microwave, and fridge.
Brand New 2 Bedroom, Greenport Village, Walk To Town Marina Views!! - Greenport, NY
9.9 82 reviews

Brand New 2 Bedroom, Greenport Village, Walk To Town Marina Views!!

apartment, Greenport
This house is located in Greenport, within a 1.6 km walk of Eastern Long Island Hospital and Stony Brook Eastern Long Island Hospital, and a 2.4 km walk from the Greenport Farmers' Market, Camera Obscura, and Greenport Carousel. Greenport Station is a 2.2 km walk away, making it easy to explore the town and surrounding areas. The house has received excellent ratings for location, cleanliness, and overall user experience, indicating a comfortable and enjoyable stay.
This property offers a spacious living area, a fully equipped kitchen, a garden, and a terrace. Enjoy amenities such as a swimming pool, a spa, parking, and free Wi-Fi, perfect for a relaxing and enjoyable getaway.
Spacious 5 Bedroom Family Beach Getaway In Charming East Marion/greenport - Greenport, NY
10 4 reviews

Spacious 5 Bedroom Family Beach Getaway In Charming East Marion/greenport

apartment, East Marion
This East Marion flat is situated a 7-minute walk from Island's End Golf and Country Club and a 2-minute drive from Kontokosta Winery, offering convenient access to local attractions.
This 4-bedroom, 3-bathroom apartment accommodates up to 10 guests and features a well-equipped kitchen with a microwave and dishwasher, air conditioning, Wi-Fi, and on-site parking, with a barbecue grill available for outdoor cooking.

Best Greenport, NY holiday rentals with parking

Lovely 1st Floor Of Farmhouse, Wineries/downtown - Greenport, NY
9.9 65 reviews

Lovely 1st Floor Of Farmhouse, Wineries/downtown

apartment, Greenport
This one-bedroom flat is situated in a Victorian house in Greenport, just a short walk from the village's restaurants, wineries, and beaches.
The apartment features a private entrance, a porch, a brick patio, a spacious bedroom with an en suite bathroom, a cosy den with a queen-size pull-out sofa bed, a sunny sitting room, a fully equipped kitchen, a washer and dryer, high-speed internet, and a new flat-screen TV.
Historic North Fork Retreat - Greenport, NY
9.4 10 reviews

Historic North Fork Retreat

apartment, East Marion
This century-old family residence in East Marion offers a unique historical experience, providing peaceful seclusion with easy access to the local village and the North Fork coastline, approximately 3 kilometres away.
This spacious four-bedroom, two-bathroom holiday home accommodates up to six guests, featuring a well-equipped kitchen, formal dining room, yoga area, extensive outdoor living spaces with a garden, fire pit and grill, and entertainment options including a record player and board games.
The Greenport Bungalow - Greenport, NY
9.9 295 reviews

The Greenport Bungalow

apartment, Greenport
This modern three-bedroom bungalow in Greenport Village is ideally located less than a kilometre from the beach, the town centre, the Shelter Island Ferry, and the Long Island Railroad.
The property offers a spacious backyard, a master bedroom with an ensuite bathroom and walk-in closets, and a fully equipped kitchen with a fridge, microwave oven, and dishwasher, making it perfect for families or groups of up to five guests.
Chic Shelter Island A-frame With Private Pool, Stylish Interiors, And... - Greenport, NY
No reviews

Chic Shelter Island A-frame With Private Pool, Stylish Interiors, And...

apartment, Shelter Island
This Shelter Island holiday home, located near beaches and a 1.4km walk from Whale's Tail Park and a 2.1km walk from Havens House, offers convenient on-site parking.
The three-bedroom, two-bathroom property boasts a fully equipped kitchen, air conditioning, a private terrace, swimming pool, garden, Wi-Fi, and in-unit laundry facilities, comfortably sleeping up to six guests.

Top-Rated Luxury Holiday Rentals in Greenport, NY, United States

Live the ultimate island dream with upscale seaside architecture and absolute privacy at luxury holiday rentals in Greenport, NY, United States.

Scrimshander House - Greenport, NY
10 80 reviews

Scrimshander House

apartment, Greenport

Top-Rated Downtown Holiday Rentals in Greenport, NY, United States

Stay steps away from local fish markets, surf shops, and seashore bars at holiday rentals in the heart of Greenport, NY, United States.

Waterfront Greenport Boathouse - Greenport, NY
9.9 34 reviews

Waterfront Greenport Boathouse

apartment, Greenport
Family And Friends In Historic Greenport House - Greenport, NY
9.7 91 reviews

Family And Friends In Historic Greenport House

apartment, Greenport
Beautifully Renovated 2 Bedroom, 1st Floor Apt -Greenport Village, Walk To Town! - Greenport, NY
9.8 79 reviews

Beautifully Renovated 2 Bedroom, 1st Floor Apt -Greenport Village, Walk To Town!

apartment, Greenport
3 Min Walk To Beach| 1 Mile To Town | Fam-friendly - Greenport, NY
10 69 reviews

3 Min Walk To Beach| 1 Mile To Town | Fam-friendly

apartment, Greenport

Top-Rated Holiday Rentals near the Ocean in Greenport, NY, United States

Open your glass doors and step directly from your living room onto the warm sand at seashore holiday rentals in Greenport, NY, United States.

Beachfront Heated Pool Hot Tub Orient Village Modern Dream Home - Greenport, NY
9.6 11 reviews

Beachfront Heated Pool Hot Tub Orient Village Modern Dream Home

apartment, Orient
Aqua Vista - Greenport, NY
9.9 748 reviews

Aqua Vista

apartment, Greenport
Beachfront Heated Pool Hot Tub Orient Village - Greenport, NY
9.7 26 reviews

Beachfront Heated Pool Hot Tub Orient Village

apartment, Orient
Luxury By The Sea!! - Greenport, NY
9.9 56 reviews

Luxury By The Sea!!

apartment, Southold

Top-Rated Holiday Rentals with a Hot Tub in Greenport, NY, United States

Watch the sun set over the water while soaking in a steaming outdoor hot tub at island holiday rentals in Greenport, NY, United States.

Perfect House:location! Location! Location! - Greenport, NY
10 4 reviews

Perfect House:location! Location! Location!

apartment, Greenport
Stunning Sag Harbor Estate On Over 3 Acres, Pool, Tennis, Perfect For Families - Greenport, NY
No reviews

Stunning Sag Harbor Estate On Over 3 Acres, Pool, Tennis, Perfect For Families

apartment, North Haven
Superb Shelter Island 4 Bed Designer With A Pool - Greenport, NY
10 7 reviews

Superb Shelter Island 4 Bed Designer With A Pool

house, Shelter Island Heights
Waterfront + Hot Tub - Greenport, NY
9.7 87 reviews

Waterfront + Hot Tub

apartment, East Marion
©2026 cozycozy.com