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Holiday Homes in Greenport

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Featured Holiday Homes in Greenport

Charming Two-Story Retreat in Southampton Village walk to town, beach and train.

10.0 out of 10, Exceptional, (8)
"Michael's cottage was incredibly well-appointed. The location to Southampton, Coopers Beach and neighboring townships made this very convenient for my trip. The true star of this cottage is the upstairs deck which was perfect for relaxing and stargazing. I will certainly return next summer. "
Charming Two-Story Retreat in Southampton Village walk to town, beach and train.

Hamptons Retreat

Hamptons Retreat

Sag Harbor Village Gem

10.0 out of 10, Exceptional, (42)
"Clean and friendly, great location"
Sag Harbor Village Gem

Shoreline Oasis

6.0 out of 10, (1)
"So the listing said house number 26 but it's really 25. So we circled the block a few times. Then the key was not in the key safe. Called the owner who apologized profusely. Had to wait a half hour for the key. Not ideal. Otherwise ok. "
The price is NZ$437
includes taxes & fees
15 July - 16 July
Shoreline Oasis

Perfect Mid-Century Private Waterfront East Hampton Retreat!

10.0 out of 10, Exceptional, (79)
"Very nice and relaxing stay in Springs! "
Perfect Mid-Century Private Waterfront East Hampton Retreat!

Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

10.0 out of 10, Exceptional, (88)
"Beautiful house with lots of light and comfort. Excellent quiet location by the ocean with outstanding communication with the host who answered all pertinent questions and addressed all outstanding issues. "
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

Driftwood Cottage by RoveTravel| 3BR Quiet Cottage

9.4 out of 10, Exceptional, (10)
"Great for families!"
Driftwood Cottage by RoveTravel| 3BR Quiet Cottage

Walk to the beach from 4 Bedroom house in Amagansett - Private Beach Path Access

Walk to the beach from 4 Bedroom house in Amagansett - Private Beach Path Access

Another rental season is coming up.

10.0 out of 10, Exceptional, (15)
"Absolutely beautiful home with everything you need for an enjoyable vacation. The host was a pleasure to work with making sure we were comfortable with our accommodations. Definitely a great place to stay. "
Another rental season is coming up.

Perfection in Sag Harbor : 5 Bedrooms with saltwater pool - walk to Beach

10.0 out of 10, Exceptional, (2)
"The property was exactly as posted. The host was great, super helpful and responsive. The pool was awesome for the kids. It was private and a wonderful stay in Sag Harbor. The town was cute and close. We would definitely stay again ! Thanks so much!"
The price is NZ$2,063
includes taxes & fees
20 July - 21 July
Perfection in Sag Harbor : 5 Bedrooms with saltwater pool - walk to Beach

The Cooper-Burke House

10.0 out of 10, Exceptional, (27)
"Nice location and house "
The Cooper-Burke House

Southampton Newly-renovated Home / Heated Pool!

10.0 out of 10, Exceptional, (28)
"We’ll kept - great layout, great backyard would love to go bakc"
Southampton Newly-renovated Home / Heated Pool!

Perfect beach house getaway within walking distance to the beach

8.6 out of 10, Excellent, (7)
"Great weekend getaway - close to the beaches and towns. Lovely little house with firepit and very quiet neighborhood."
Perfect beach house getaway within walking distance to the beach

July Flash Sale: Luxury Beach House, Heated Pool, Dune Rd beaches, pets ok

10.0 out of 10, Exceptional, (10)
"An absolute perfect home for a family looking to enjoy"
July Flash Sale: Luxury Beach House, Heated Pool, Dune Rd beaches, pets ok

Heated pool/5 min walk to Beach/Beautiful Sag Harbor Village /Restaurant/Museum

10.0 out of 10, Exceptional, (45)
"Great house, kitchen is well equipped which made dining in very easy. Loved the pool and backyard."
Heated pool/5 min walk to Beach/Beautiful Sag Harbor Village /Restaurant/Museum

Charming 3-bedroom, 3 bath house in l Sag village, Harbor with pool, AC, WiFi

2.0 star property
8.0 out of 10, Very good, (6)
"We had a fantastic stay! The home was exactly as described — clean and very comfortable. The location was perfect. We loved being close to town. Communication was smooth and easy — Frank was quick to respond. We’d absolutely stay here again and recommend it to anyone visiting the area! "
The price is NZ$1,196
includes taxes & fees
5 Aug - 6 Aug
Charming 3-bedroom, 3 bath house in l Sag village, Harbor with pool, AC, WiFi

Newly Renovated, Centrally Located East Hampton Home, Total Privacy,...

10.0 out of 10, Exceptional, (2)
"Great house!"
Newly Renovated, Centrally Located East Hampton Home, Total Privacy,...

Prime location! Walk to Beach! Wainscott Family House & Cottage. Pool & Hot Tub!

10.0 out of 10, Exceptional, (26)
"Perfect location for a family trip! Great property to just hang by the pool & enjoy the large back yard. Nice bike ride past a farm stand to get to the beautiful beach. Love the surrounding farms & proximity to the beach"
Prime location! Walk to Beach! Wainscott Family House & Cottage. Pool & Hot Tub!

Open Floor Plan, Extensive Decking, Close to Gardiners Bay Beach and...

9.4 out of 10, Exceptional, (13)
"Amazing place, we loved our stay!"
Open Floor Plan, Extensive Decking, Close to Gardiners Bay Beach and...

Beachfront Bliss , Inviting 3 bedroom + loft at Hawks Nest Beach!

4.8 out of 10, (3)
"Overall, my girlfriends and I had a good stay at this accommodation. Transparently, there were some hiccups in communication between the property manager and I in the week leading up to our trip that were not clearly stated in the home's description prior to us booking our stay, however, I felt that they were able to address my concerns and came up with solutions that felt satisfactory to my group and I. The property manager was overall understanding and receptive to my feedback through our...
Beachfront Bliss , Inviting 3 bedroom + loft at Hawks Nest Beach!
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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