
Holiday houses in Greenport
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Top-rated holiday rentals in Greenport
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Other great holiday rentals in Greenport
Superhost

Cabin in Shirley
4.87 out of 5 average rating, 153 reviewsA-Frame cabin with private beach & epic sunsets
JenniferRating, 5 stars1 week ago
Amber’s place was immaculate and stunning. This was my 2nd time staying and it was just as magical! The place had plenty of space for a family of 3 and the washer/dryer was very convenient. We had a great time and would stay here again!
Top Guest favourite

Cottage in Guilford
4.99 out of 5 average rating, 136 reviews"Red House on the Knoll" at Indian Cove
MaryRating, 5 stars1 week ago
My family and I loved staying at Gail’s place! We grew up in Madison and were back for a visit. It was such a great place and allowed us to re-live many fond memories of growing up in the area!
Guest favourite

Home in North Fork
5 out of 5 average rating, 9 reviewsKayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV
KristinaRating, 5 stars3 days ago
Had a wonderful time over Easter with my family and dog. The view was exquisite and the house very comfortable. Eileen was very responsive and even had hair dryers sent over. The house was very well equipped with lots of kitchen staple goods. Just be aware there is no microwave, but there is a very nice Breville toaster oven. Also, there is a large table outside for a group, but only a small table and counter seating in kitchen inside. We didn't have any issue since the weather was perfect for us to enjoy our Easter dinner outside. Overall, a beautiful home and only minutes from Greenport and wineries.
Superhost

Home in Waterford
4.94 out of 5 average rating, 18 reviewsSummer Beach Cottage Harknes, Ocean Beach N
JenniferRating, 5 stars7 months ago
It was a perfect spot for our little family vacation. We were so close to a few really nice beaches and the area is a short drive to mystic aquarium and village. Patsy and family are very nice and gave some great suggestions for activities in the area.
Guest favourite

Cabin in Rocky Point
4.89 out of 5 average rating, 484 reviewsGreat little place just for a couple
AllaireRating, 5 stars4 days ago
We had a great time staying with Marina. The space was so clean and the perfect size for two adults and our senior pup. The outdoor space was beautifully landscaped and the beach was only a 5 minute walk. We would definitely come back!
Guest favourite

Guesthouse in Shelter Island
4.96 out of 5 average rating, 27 reviewsSleek and Chic cottage/Pool House
YuryRating, 5 stars11 months ago
Perfect getaway in Shelter Island! The pool house is as amazing as it looks in the listing :) Cute house on a beautiful, peaceful and very private green lot. Primael was very welcoming and responsive. She was also very flexible in terms of our check in and check out. Everything went super smoothly. We enjoyed our stay a lot!
Guest favourite

Home in Woodmont
4.98 out of 5 average rating, 43 reviewsBeachfront paradise- come, stay, relax!
TheoRating, 5 stars3 months ago
we rented La Spiaggia in December, and while it's mostly going to be more beautiful and better in the summer (since it's a beach house) it was still perfectly fine in the winter; well insulated and with good strong heaters. speaking of the beach I can't stress enough of how close this place is to the water; I'm talking literally ten steps to the sand. I would certainly recommend the place as a great summer getaway!
Top Guest favourite

Home in Old Saybrook
5 out of 5 average rating, 49 reviewsGreat Hammcock Getaway, Nearby beaches, Hot tub
DavidRating, 5 stars1 month ago
What a beautiful place and conveniently located. The house was wonderful decorated, was very comfortable and definitely was a relaxing place to get away. Irina was a wonderful host and the home had many wonderful amenities to offer.
Quick stats about holiday rentals in Greenport
Total rentals
170 properties
Nightly prices starting at
$187 AUD before taxes and fees
Total number of reviews
9.8K reviews
Family-friendly rentals
120 properties are a good fit for families
Pet-friendly rentals
50 properties allow pets
Rentals with a pool
30 properties have a pool
Destinations to explore
- The Hamptons Holiday rentals
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- Rentals with pools Greenport
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- Beach
- Yale University
- Foxwoods Resort Casino
- Ocean Beach Park
- Cooper's Beach, Southampton
- Quotonset Beach
- Giants Neck Beach
- Shinnecock Hills Golf Club
- Woodmont Beach
- Clinton Town Beach
- Walnut Public Beach
- TPC River Highlands
- Amagansett Beach
- Blue Shutters Beach
- Jennings Beach
- Seaside Beach
- Shennecossett Beach
- Connetquot River State Park Preserve
- Long Island Aquarium
- Attawan Beach
- Groton Long Point Main Beach
- Bushnell Park
- Sunken Meadow State Park
- Burwells Beach