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Compare 1447 Vacation Homes in Greenport with updated reviews, rates, and availability.

Gorgeous private Hamptons house with pool and volleyball court
8.4 out of 10, Very Good, (17)
"Enjoyed this house in a great location. It was perfect for attending a family wedding!"
Gorgeous private Hamptons house with pool and volleyball court
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
10.0 out of 10, Exceptional, (16)
"Our group of friends stayed at this house for a long weekend in October 2024. The house is just as good or better than the pictures in the listing. Very clean and updated inside and out. Most importantly, the bathrooms and kitchen are clean and updated. And the huge backyard with pool, hot tub, and outdoor shower takes this house to the next level. The backyard space is great for families, small groups, or anyone looking for a quiet private space to relax. The owner/manager was very...
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Waterfront Beach House
9.6 out of 10, Exceptional, (39)
"This was perfect for us. We had a family funeral and this was a nice retreat. We would stay again for sure. "
Waterfront Beach House
Holiday Specials!!!/Out Door Theater Fire Pit/ Bocce court- WATCH VIDEO!!!
10.0 out of 10, Exceptional, (34)
"This home is quintessentially charming! I arrived late at night, alone. It has a charming curved drive in and there sat the wood home with a large front porch and Forrest behind it. It seemed like little house on a prairie with the porch and dormer windows. The motion lights went on immediately, which I was grateful for. There is a narrow stairwell up to 3 bedrooms, as is customary in older style homes. High ceilings and windows everywhere enhance this property. When I woke there was a family of...
Holiday Specials!!!/Out Door Theater Fire Pit/ Bocce court- WATCH VIDEO!!!
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
9.0 out of 10, Wonderful, (86)
"Very cute ranch in a lovely neighborhood. Good location for access to area sites like Hammonasset Beach, Chamard Vineyard, and the Water's Edge. Not truly a "water's view", but the house had all the amenities needed for a fun stay! "
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
Oceanfront Beach House lay in bed and hear the waves, boats , birds
10.0 out of 10, Exceptional, (17)
"We enjoyed the house and location very much. Perfect for our little part. "
Oceanfront Beach House lay in bed and hear the waves, boats , birds
Historic Essex Home w/ Large Yard Near Downtown!
9.8 out of 10, Exceptional, (40)
"All bedrooms up were difficult with luggage. Fully equipped for an extended stay would be convenient. Very close to marina and shopping."
Historic Essex Home w/ Large Yard Near Downtown!
Quaint Family-sized Home w/private beach — 5 minutes from wineries!
9.6 out of 10, Exceptional, (10)
"Excellent "
Quaint Family-sized Home w/private beach — 5 minutes from wineries!
Northfork Townhouse- walk to all/ newly renovated
9.4 out of 10, Exceptional, (3)
"The place was as advertised and in great walking distance to everything in town! "
Northfork Townhouse- walk to all/ newly renovated
COZY COTTAGE WITH PRIVATE BEACH ACCESS IN THE DUNES - Half a block to the beach
10.0 out of 10, Exceptional, (13)
"Steps to probably the most beautiful beach in the Hamptons. Thoroughly enjoyed our stay, as did the dogs. We will definitely be back."
COZY COTTAGE WITH PRIVATE BEACH ACCESS IN THE DUNES - Half a block to the beach
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
2.5 star property
10.0 out of 10, Exceptional, (6)
"Great bungalow for weekend getaway. New building with spacious shower and access to pool and hot tub. In a very quiet area of Bridgehampton with close access to restaurants and shopping. Host was very responsive and helpful. "
The price is AED 716
AED 1,420 total
includes taxes & fees
2 Dec - 3 Dec
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
Sagaponack, Hamptons Designer Luxury, Tennis Court and 8 Bedrooms
10.0 out of 10, Exceptional, (18)
"Exceptional property, extremely well designed, location is outstanding; it is a true Hamptons Estate fit ideally for family stays and relaxing experience. "
Sagaponack, Hamptons Designer Luxury, Tennis Court and 8 Bedrooms
PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH
10.0 out of 10, Exceptional, (11)
"The house is very nice. Very updated and clean. Best bathrooms in any house we have stayed in. The kitchen was large and very nice. Backyard is nice and private with plenty of room. My only issue is that there are so many trees that it blocks a lot of the sun. The pool is in the shade most of the time. In the hot summer it might be great to get some shade but our week was in the low 70's and we could have used a little more sun on the pool. House is in a good location, close to town and the...
PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH
Beach House
9.8 out of 10, Exceptional, (47)
"It's Christmas all year and we loved it! So so cozy. From my elderly mom to my toddler everyone was happy. Kids lived the playground and we loved how easy and comfortable the house was. Joe also left us delicious cookies from a local bakery. Thank you Joe!!! "
Beach House
Fall in the🌅beautiful sunsets
10.0 out of 10, Exceptional, (24)
"Margaret is just wonderful. We felt like we were staying at a dear family member’s home. Stayed in her very private upstairs suite and it was perfect for me, my wife and our pup. He had a blast running around the yard, meeting the chickens going to the bay beach etc. We had the best time! Thank you Margaret!!"
Fall in the🌅beautiful sunsets
2 Bedroom Hamptons Waterfront Cottage Rental
10.0 out of 10, Exceptional, (10)
"Everything first class. Air co and heat units in each tooth Everything thing you might need for a great vacation "
2 Bedroom Hamptons Waterfront Cottage Rental
OCEAN/BEACH FRONT, HUGE YARD, SUNSET VIEW
9.4 out of 10, Exceptional, (33)
"Our second stay at the cottage. We spent a long weekend and the weather cooperated. The house is quite quirky, but has a really pleasant feel at home vibe. Beds were very comfortable. Kitchen could use some updates, but was sufficient. (still need a new can opener) The porch overlooking the Sound is magical. Nice neighborhood. If you have one...bring a golf cart! Lots of golf carts about. Host is always pleasant, communicating through Vrbo. We hope to return again. Thank you Khalig Family...
OCEAN/BEACH FRONT, HUGE YARD, SUNSET VIEW
Welcome to the J Luxury Southampton Estate w/Pool
9.8 out of 10, Exceptional, (30)
"Joe was an amazing host - always responsive from the moment of booking throughout the entire stay. The kitchen was a chef's dream - spacious and stocked with every appliance, seasoning, etc you can think of. We were a group of 8 and cooked family dinners each night. The highlight of the property was most definitely the deck, which was beautifully decorated and with a perfect amount of seating. Neighborhood was very walkable and it was a very short drive to the beach! I would note that there are...
Welcome to the J Luxury Southampton Estate w/Pool
Ocean Beach Park Lawrence M.Hosp MitchellCollege Coast Guard Academy CT College
9.6 out of 10, Exceptional, (44)
"We loved being next door to Ocean Beach."
Ocean Beach Park Lawrence M.Hosp MitchellCollege Coast Guard Academy CT College
Historic Luxury Seaside Getaway
10.0 out of 10, Exceptional, (32)
"We loved o weekend getaway with the family. The house was beautiful. Everything was perfect. "
Historic Luxury Seaside Getaway
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.
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Other property types in Greenport

Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (206)
"Stove it’s not efficient and refrigerator blocked with the corner of wall"
Cliffside Resort Condominiums
Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, (262)
"smooth check in, very clean place, via text comunication extremely effective, we also loved the small kitchen in the room, ideal for some coffee making or warming ubp a bite we simply loved the place."
The price is AED 464
AED 609 total
includes taxes & fees
2 Dec - 3 Dec
Windward Shores Ocean Resort
Driftwood Resort
3.5 star property
9.0 out of 10, Wonderful, (212)
"Well kept. Everything in good working order. Easy check in/out. Very good communication. Enjoyed our second time here. "
Driftwood Resort
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.