Photo by Nina Dinoff

Greenport Vacation Rentals

Vacation Rentals in Greenport

Cliffside Resort Condominiums
Beach nearby
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, 183 reviews
"Wonderful stay and super clean! Can’t wait to come back. "
The price is $296
$381 total
includes taxes & fees
Jun 11 - Jun 12
Cliffside Resort Condominiums
Windward Shores Ocean Resort
View from property
Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, 238 reviews
"Good family friendly resort! Hope it’s a heated pool.. Easy Check-out before 11:00 am!"
The price is $242
$297 total
includes taxes & fees
Jun 9 - Jun 10
Windward Shores Ocean Resort
Driftwood Resort
Apartment, 1 Bedroom | Private kitchen | Fridge, microwave, cookware/dishes/utensils
Driftwood Resort
3.5 star property
8.8 out of 10, Excellent, 188 reviews
"Well maintained upscale resort. "
The price is $198
$248 total
includes taxes & fees
Jun 9 - Jun 10
Driftwood Resort
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool
Outdoor pool, a heated pool
Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool
9.6 out of 10, Exceptional, 50 reviews
"Close to the restaurants and beaches. We enjoyed exploring the nearby areas within 15 to 30 mins drive"
Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool
Sagaponack Grand Estate, With Tennis Court, Newly-Furnished and 8 Bedrooms
Outdoor pool, a heated pool
Sagaponack Grand Estate, With Tennis Court, Newly-Furnished and 8 Bedrooms
10.0 out of 10, Exceptional, 12 reviews
"Incredible property, incredible people to work with! We this is our second year in a row renting this house for a holiday weekend, and we look forward to renting every year forward! The house itself is stunning, clean and full of activities from the pool, to the tennis court, to the movie room. Rebecca and Shaun are truly a pleasure, and reply immediately to any questions, requests or needs. They even left us a welcome present for returning this year! Thank you for allowing us to have an annual...
Sagaponack Grand Estate, With Tennis Court, Newly-Furnished and 8 Bedrooms
North Fork Escape Near Wineries, Beaches And Hamptons
4 bedrooms, desk, iron/ironing board, free WiFi
North Fork Escape Near Wineries, Beaches And Hamptons
9.4 out of 10, Exceptional, 18 reviews
"Lovely quaint home. Very clean and spacious. Perfect for a family getaway . Highly recommend."
North Fork Escape Near Wineries, Beaches And Hamptons
Patchogue River Retreat, 8 minute walk to West Beach
Smart TV, fireplace
Patchogue River Retreat, 8 minute walk to West Beach
10.0 out of 10, Exceptional, 6 reviews
"House was very nice. Location is great. Easy walk to beach and convenient to Westbrook center."
Patchogue River Retreat, 8 minute walk to West Beach
Beautiful Family Home Nestled In The Heart Of Sagaponack
Outdoor pool, a heated pool
Beautiful Family Home Nestled In The Heart Of Sagaponack
10.0 out of 10, Exceptional, 25 reviews
"House was very clean and host was exceptional. Very relaxing place to stay."
Beautiful Family Home Nestled In The Heart Of Sagaponack
Ocean Beach Fun! 3 bedroomsDog ok with fee and signing of pet agreement!<br>
Pool
Ocean Beach Fun! 3 bedroomsDog ok with fee and signing of pet agreement!<br>
10.0 out of 10, Exceptional, 10 reviews
"We had a big group with all different ages. Everybody enjoyed their stay. The home was clean, comfortable, and very thoughtfully decorated. The pool table, poker table and Pac-Man kept us all entertained during out time there. Hosts were friendly and responsive."
Ocean Beach Fun! 3 bedroomsDog ok with fee and signing of pet agreement!<br>
Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
Smart TV, fireplace, stereo
Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
10.0 out of 10, Exceptional, 73 reviews
"This place exceeded all expectations, offering a perfect blend of convenience and serenity. Situated just moments from downtown, the location provided easy access to the vibrant community, while still offering a peaceful retreat. The highlight of our stay was undoubtedly the private beach access. Tucked away in a tranquil neighborhood, it boasted unparalleled beauty and tranquility. Simply being in the vicinity was a getaway in itself, with breathtaking views that soothed the soul. The...
Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
Location and views! Located directly on Shinnecock Bay!
Smart TV
Location and views! Located directly on Shinnecock Bay!
9.2 out of 10, Wonderful, 12 reviews
"You have the opportunity to attend a graduation party at the Hamptons, where everyone had to find their own accommodations. The location is essentially located to town to the water and beautiful scenic paths. The host insured that the home was exceptionally clean and amenities provided. Not to mention accommodating due to last-minute change in schedule."
Location and views! Located directly on Shinnecock Bay!
Gorgeous private Hamptons house with pool and volleyball court
Outdoor pool
Gorgeous private Hamptons house with pool and volleyball court
7.8 out of 10, Good, 7 reviews
"This place was nice and roomy for our family of 8 plus 3 littles kiddos. Pretty clean as well. I gave listing accuracy a 5 because it is accurate but that may be because it doesn't tell you much. We were a little short on towels, many light bulbs were burnt out or just missing. We replaced some (they were there) and moved others to balance out the light. No kitchen linens, short on bath towels, short on paper towels and definitely not enough TP. 3 partial rolls and 1 bathroom had none so we had...
Gorgeous private Hamptons house with pool and volleyball court
70 Year old cottage on 2.8 acres, stunning views and sunsets
Interior
70 Year old cottage on 2.8 acres, stunning views and sunsets
70 Year old cottage on 2.8 acres, stunning views and sunsets
Steps to the Beach, Cozy Year Round Cottage 🐾 Pet Friendly
Beach nearby, beach towels
Steps to the Beach, Cozy Year Round Cottage 🐾 Pet Friendly
9.8 out of 10, Exceptional, 38 reviews
"Great place. Cozy cottage!"
Steps to the Beach, Cozy Year Round Cottage 🐾 Pet Friendly
The Bay Cottage · Rocky Neck Park, Beach & Niantic
3 bedrooms, desk, iron/ironing board, WiFi
The Bay Cottage · Rocky Neck Park, Beach & Niantic
10.0 out of 10, Exceptional, 5 reviews
"I booked this for a sister weekend. It was perfect for what we needed. It appears that the house was built to be a summer getaway, so it is pretty basic and no frills and comes with all the creaks and quicks of an older house. The living room is perfect for hanging out and the four chairs make it easy to rearrange to suit your needs. The kitchen is nicely stocked with everything you would need to stay with a family and the dining room is spacious enough to easily accommodate everyone staying...
The price is $298
$572 total
includes taxes & fees
Jun 18 - Jun 19
The Bay Cottage · Rocky Neck Park, Beach & Niantic
"Salt 'n' Lyme" - Walk to everything !
Exterior
"Salt 'n' Lyme" - Walk to everything !
9.2 out of 10, Wonderful, 21 reviews
"This cottage is so adorable and just a short walk to the beach and a local convenience store. This makes it easy to park the car and just walk to get coffee and such. We stayed in October so not much open this time of year, but we were in the area for a family wedding so not much time to hang out anyway. This was the first time I've rented on Vrbo, so I wasn't sure what to expect as have read a lot about obnoxious owners with tons of rules, but Brett is super-chill with only a couple of things...
"Salt 'n' Lyme" - Walk to everything !
Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!
Outdoor pool, a heated pool
Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!
10.0 out of 10, Exceptional, 23 reviews
"It was a great weekend"
Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!
Rustic Lakeside Cabin at White Gate Farm
Interior
Rustic Lakeside Cabin at White Gate Farm
10.0 out of 10, Exceptional, 90 reviews
"Amazing place. Amazing hosts."
Rustic Lakeside Cabin at White Gate Farm
Modern Farmhouse/Out Door Theater Fire Pit/ and Bocce court- WATCH VIDEO!!!
Outdoor dining
Modern Farmhouse/Out Door Theater Fire Pit/ and Bocce court- WATCH VIDEO!!!
10.0 out of 10, Exceptional, 28 reviews
"The house was beautiful and comfortable. We enjoyed the property and watching the wildlife. The fire pit was great for a group gathering. We didn't cook but the kitchen appeared well stocked. The house was short on paper products. We left a note for the house manager when we left."
Modern Farmhouse/Out Door Theater Fire Pit/ and Bocce court- WATCH VIDEO!!!
Contemporary home, newly built, heated pool and hot tub, large deck and...
Microwave, oven, stovetop, coffee/tea maker
Contemporary home, newly built, heated pool and hot tub, large deck and...
10.0 out of 10, Exceptional, 5 reviews
"The property manager was incredibly helpful in providing check-in and check-out information, and was readily available to answer any questions during our stay. The house perfectly matched what we saw in the photos and was ideal for our getaway. We're already looking forward to returning in the summertime to fully enjoy the pool."
Contemporary home, newly built, heated pool and hot tub, large deck and...
Don't see what you're looking for?
See all available properties in Greenport
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Greenport you may be interested in

Sound View Greenport
Lobby sitting area
Sound View Greenport
4.0 star property
8.4 out of 10, Very Good, 434 reviews
"We didn't have a table and chairs outside. We called the front desk and asked for them. They never came. We got our beach chairs out of our car to use."
The price is $336
$429 total
includes taxes & fees
Jun 12 - Jun 13
Sound View Greenport
The Harbor Front Inn
Balcony view
The Harbor Front Inn
3.5 star property
8.8 out of 10, Excellent, 358 reviews
"Hotel was cozy, great location on the main street of all entertainment. View was amazing. Will definitely stay again!"
The price is $297
$379 total
includes taxes & fees
Jun 12 - Jun 13
The Harbor Front Inn
Greenporter Hotel
Property grounds
Greenporter Hotel
2.0 star property
9.4 out of 10, Exceptional, 56 reviews
"Great location and accomodations. Bed was very comfortable. Property was exceptionally clean. Service was difficult in the mornings because sane person was running the cafe and front desk so he had to keep running back and forth. He did a great job given the circumstances and was very pleasant.Wish the cafe was open every evening for those guests who are staying during the week. Nice place to finish the day. Alex was a great bartender. Overall great stay."
The price is $251
$301 total
includes taxes & fees
Jun 19 - Jun 20
Greenporter Hotel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Everything you need to know about Greenport vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Greenport vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Greenport vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Greenport vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Greenport. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Greenport in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $198 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Greenport rentals

At Expedia, we put the best Greenport vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Greenport rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Greenport vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Greenport. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a vacation rental in Greenport?

Yes, we give you a choice of vacation rentals in Greenport near Railroad Museum of Long Island, or you can select a more remote option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the beaches in Greenport. Make sure you have time to check out the waterfront and festivals during your trip.

What are some of the best vacation home rentals that Greenport has to offer?

Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool: This vacation home near Greenport offers an outdoor pool, a fireplace, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals are there in Greenport?

With 102 Expedia vacation rentals, you're sure to find just the right place for your Greenport stay.

What can I see and do in Greenport?

Enjoy the outdoors at 67 Steps Beach and Norman E. Klipp Marine Park, or simply take in cultural attractions like Railroad Museum of Long Island and East End Seaport Maritime Museum. While here, Greenport Carousel and Kontokosta Winery are other places worth a visit.

What are vacation rentals like in Greenport?

Vacation rentals are privately owned properties you can stay in for a couple days or more in Greenport. Vacation rentals feature amenities like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about a sanitized environment, vacation rentals can offer a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for a family getaway.

Recent reviews of Greenport properties
Expedia verified reviews

Southampton Inn

Southampton Inn

5/5 Excellent
"ALWAYS A good experience "
A verified traveler from Old Brookville stayed at Southampton Inn
Posted 8 hours ago
Southampton Inn