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Check prices for these dates

Next weekend
31 Jan - 2 Feb
In two weeks
7 Feb - 9 Feb
In one month
21 Feb - 23 Feb
In two months
21 Mar - 23 Mar

Compare 1432 Vacation Homes in Greenport with updated reviews, rates, and availability.

Enjoy Autumn with us.
Exterior

Enjoy Autumn with us.

10.0 out of 10, Exceptional, (13)
"Ladies weekend. The home was clean and comfortable. We loved how all the kitchen cabinets and drawers were labeled. The host was responsive and accessible The neighborhood was beautiful and close to several of the wineries "
Enjoy Autumn with us.
Cozy Westbrook Vacation Rental - Walk to Beach!
Westbrook Vacation Rental | 3BR | 1.5BA | 1 Step to Enter | 1,350 Sq Ft

Cozy Westbrook Vacation Rental - Walk to Beach!

10.0 out of 10, Exceptional, (11)
"Stayed at this house for a weekend after Christmas. It was great! Perfect location and easy to get everywhere! Would love to stay again."
Cozy Westbrook Vacation Rental - Walk to Beach!
Beautiful Private 4 BR, Heated Pool. Close to Everything.
New Teak Lounge Chairs, Decking and Pool Liner

Beautiful Private 4 BR, Heated Pool. Close to Everything.

9.6 out of 10, Exceptional, (42)
"We were in the Hamptons to celebrate my sisters upcoming wedding and had a fantastic time in our rental the only complaint we had was that wish we were there longer!"
Beautiful Private 4 BR, Heated Pool. Close to Everything.
Village Fringe Available May 24th - October 31st. Family/Pet Friendly
Pool

Village Fringe Available May 24th - October 31st. Family/Pet Friendly

10.0 out of 10, Exceptional, (21)
"Very nice home and location, lovely and helpful owner!"
Village Fringe Available May 24th - October 31st. Family/Pet Friendly
COZY COTTAGE WITH PRIVATE BEACH ACCESS IN THE DUNES - Half a block to the beach
Outdoor dining

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
Mid-Century Winter Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
Pool

Mid-Century Winter Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!

10.0 out of 10, Exceptional, (81)
"Very relaxing place to stay 2 minutes from the beach and fabulous sunsets. Property was spotless with tons of room. "
Mid-Century Winter Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
Gorgeous private Hamptons house with pool and volleyball court
Exterior

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
Ocean Beach Fun! 3 bedroomsDog ok with fee and signing of pet agreement!<br>
Living room with big sectional

Ocean Beach Fun! 3 bedroomsDog ok with fee and signing of pet agreement!<br>

10.0 out of 10, Exceptional, (22)
"This house that we stayed at was amazing. Room for everyone, plenty of entertainment, and the neighborhood was quiet. Mary was also very responsive & available for any questions we had. Will definitely stay here again! 5"
Ocean Beach Fun! 3 bedroomsDog ok with fee and signing of pet agreement!<br>
Fall in the🌅beautiful sunsets
1860 farm 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
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Sprawling pool with outdoor kitchen

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

10.0 out of 10, Exceptional, (18)
"My friends and I stayed at this house for a few days around New Year's. The house is very spacious, and the grounds are lovely. We had a group of 5 and had lots of room to congregate and disappear if we needed alone time. The hot tub was exactly what some of us needed, while the kitchen provided others with much comfort. The one bummer was when we arrived; it looked like someone had just had a party outside so that first made for a bit of cleanup. That little bump shouldn't stop you from...
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons
Exterior

Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons

10.0 out of 10, Exceptional, (5)
"Perfect getaway for a group of ladies spending a snowy night catching up away from our spouses and kids. Cozy fireplace, beautiful home, ample space and in a great location. Highly recommend!"
The price is AED 1,950
AED 3,593 total
includes taxes & fees
2 Feb - 3 Feb
Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons
Ocean Beach Park Lawrence M.Hosp MitchellCollege Coast Guard Academy CT College
1st Fl. Living room

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
Beautiful Hamptons home close to beaches, shopping, & restaurants!
Pool

Beautiful Hamptons home close to beaches, shopping, & restaurants!

10.0 out of 10, Exceptional, (8)
"Had a great stay! Everything about the stay was perfect. Place was all that we expected and more. Host was easy to reach and very responsive. "
Beautiful Hamptons home close to beaches, shopping, & restaurants!
Walk to the beach at Black Point, Niantic, Ct.
Niantic Bay from end of driveway.

Walk to the beach at Black Point, Niantic, Ct.

9.8 out of 10, Exceptional, (86)
"Wonderful space in a beautiful quiet neighborhood near ocean and cute small town if Niantic"
Walk to the beach at Black Point, Niantic, Ct.
Expansive Beautiful Ranch with Pool and hot tub. Close to Beach Sleeps 20+
Exterior

Expansive Beautiful Ranch with Pool and hot tub. Close to Beach Sleeps 20+

10.0 out of 10, Exceptional, (10)
"This may very well be the nicest house we have ever stayed in! It was spacious, clean and well stocked. It was so nice not to have to bring our own linens! We were pleasantly surprised with a hot tub. Thank you for a great stay!"
Expansive Beautiful Ranch with Pool and hot tub. Close to Beach Sleeps 20+
The beach is waiting.
Exterior

The beach is waiting.

10.0 out of 10, Exceptional, (25)
"Susan's place was perfect for my family to visit the neighborhood where I grew up! It was clean, comfortable and had everything we needed. It's also a few steps from the beach and the amenities GNB has to offer."
The beach is waiting.
Steps to beach! Custom-built house with panoramic ocean views, wrap-around deck.
Raised deck dining and lounging set; additional dining chairs not pictured

Steps to beach! Custom-built house with panoramic ocean views, wrap-around deck.

10.0 out of 10, Exceptional, (42)
"This property is beautiful and the house is spacious and well equipped for a wonderful stay. The host was attentive and easy to contact when it was necessary. Such a fantastic choice for a stay in a delightful town. "
Steps to beach! Custom-built house with panoramic ocean views, wrap-around deck.
Beautiful Southampton Home One Block from Shinnecock Bay, Town Shopping,...
Pool

Beautiful Southampton Home One Block from Shinnecock Bay, Town Shopping,...

9.4 out of 10, Exceptional, (3)
"We loved being together and the house and pool made it ideal for two weeks with an infant. We wished that there was better information/communication about lawn and pool service, pest treatment and trash pick-up. We were also bit disappointed that the outdoor table was not replace and we could not do any outdoor dinners."
Beautiful Southampton Home One Block from Shinnecock Bay, Town Shopping,...
Waterford Manitock Spring Water Residence with handicap accessible home
Living area

Waterford Manitock Spring Water Residence with handicap accessible home

10.0 out of 10, Exceptional, (4)
"I recently had the pleasure of staying at the Manitock Spring Water Residence in Waterford, Connecticut, and it was a delightful experience. The home is thoughtfully designed with handicap accessibility, ensuring comfort for all guests. Its location is ideal, with Lawrence + Memorial Hospital, Flanders Plaza Shopping Center, Hempstead Houses and Mystic all within a short drive. The open-concept design of the dining room and kitchen creates an airy and inviting atmosphere. The host was attentive...
Waterford Manitock Spring Water Residence with handicap accessible home
Best location! Cozy and Chic Retreat 5 min to beach and close to town, peaceful!
Upstairs living room, with high ceilings, natural light + comfortable furniture

Best location! Cozy and Chic Retreat 5 min to beach and close to town, peaceful!

9.8 out of 10, Exceptional, (7)
"Family friendly, clean and well-stocked house with nice deck and pool for entertaining. It has personality. Well stocked kitchen (note - includes french press and a pod system but you need to bring your own pods; no coffee maker or kettle at time of our stay). Plenty of spices and condiments and entertaining ware as this is also their vacation home. Conveniently located near the highway and walkable to commercial area and 10 min drive to nearest beaches (it does back up to highway so gets road...
Best location! Cozy and Chic Retreat 5 min to beach and close to town, peaceful!
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
Room

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (207)
"Stove it’s not efficient and refrigerator blocked with the corner of wall"
Cliffside Resort Condominiums
Windward Shores Ocean Resort
Property grounds

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (267)
"Perfect location for a peaceful winter weekend getaway. We’ve stayed here before and definitely will again. "
The price is AED 464
AED 609 total
includes taxes & fees
26 Jan - 27 Jan
Windward Shores Ocean Resort
Sagaponack, Hamptons Designer Luxury, Tennis Court and 8 Bedrooms
Pool

Sagaponack, Hamptons Designer Luxury, Tennis Court and 8 Bedrooms

10.0 out of 10, Exceptional, (18)
"The property was amazing and I highly recommend it! From the initial reservation to check-out - just fabulous! I have already suggested to 2 friends. "
Sagaponack, Hamptons Designer Luxury, Tennis Court and 8 Bedrooms
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.