Photo by Nina Dinoff

Holiday Rentals in Greenport

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Holiday Rentals in Greenport

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

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 €145
includes taxes & fees
23 Jan - 24 Jan
Windward Shores Ocean Resort

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

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

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>

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>

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!!!

Beautiful Family Home Nestled In The Heart Of Sagaponack

10.0 out of 10, Exceptional, (30)
"Great space and location. We loved the house and enjoyed our stay. "
Beautiful Family Home Nestled In The Heart Of Sagaponack

Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round

9.8 out of 10, Exceptional, (106)
"Wonderful place to spend time with the family in this cozy cottage. Would love to come back in the summer to enjoy the beach. "
The price is €501
includes taxes & fees
20 Jan - 21 Jan
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round

Summer getaway

9.2 out of 10, Wonderful, (10)
"Overall, we had a terrific time at the house. Thank-you so much Andres for sharing your home with us. Getting there, checking in, all simple and easy. House was very well stocked. There was plenty of room for the eight of us. The beds were all comfortable. The deck was delightful. A couple of minor things that we had happen, or noticed that might want to be addressed. Given the house is controlled by Alexa, some detailed instructions as to how to work with "her" might be a good idea for...
Summer getaway

Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!

10.0 out of 10, Exceptional, (33)
"The house was perfect, a home away from home located in a nice quiet area, with stores and restaurants close by. House was clean, spacious and stocked with the essentials. The kids loved the pool and the ping pong table. Thank you Val for the perfect weekend, hope to see you next Summer!!"
Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!

Rustic Lakeside Cabin at White Gate Farm

10.0 out of 10, Exceptional, (106)
"Ideal venue for peace, quiet and unplugged introspection."
Rustic Lakeside Cabin at White Gate Farm

Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

9.8 out of 10, Exceptional, (26)
"When my hometown sib couldn't host, we rented here and had our family Thanksgiving! It was great!"
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

Driftwood Resort

3.5 star property
9.0 out of 10, Wonderful, (212)
"We were visiting our so. And just needed an inexpensive..relatively..place to stay….. this was quite convenient…. We had a good night sleep…took a walk to beach..had a great chat with one of the ‘beach boys’ and thought it was lovely……"
Driftwood Resort

70 Year old cottage on 2.8 acres, stunning views and sunsets

8.4 out of 10, Very good, (6)
"We all liove the various Connecticut shore towns, and Ild Lyme was delightful. We revisited some favorite spots, and discovered a few new ones. The vintage appliances were particularly nice to find, and looking at old photos, we realized that the original cottage was really 100 years old!"
70 Year old cottage on 2.8 acres, stunning views and sunsets

Private 2.1 acre gated home with heated pool and tennis & pickleball court

10.0 out of 10, Exceptional, (18)
"My family and I went to the Southamptons for our Christmas vacation. Since it was during the winter we didn’t try out the on-site tennis court or pool. The house is gorgeous and looks exactly as advertised. The host was in communication from 2-days before we arrived until checkout to assist as needed. We brought most of our gifts and a pop-up tree. All rooms have their own bathroom which is convenient. Plenty of linens and anything else you may need. If you’re used to using more than one oven...
Private 2.1 acre gated home with heated pool and tennis & pickleball court

Location and views! Located directly on Shinnecock Bay!

9.2 out of 10, Wonderful, (23)
"Stay was relaxing, space was very cozy. we enjoyed our stay. "
Location and views! Located directly on Shinnecock Bay!

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

Southampton Serenity Walk to beach. Kayaks on lake Park-like grounds Pool Tennis

9.8 out of 10, Exceptional, (25)
"Ken was great and easy to work with. The house was nice and perfect for our stay!"
Southampton Serenity Walk to beach. Kayaks on lake Park-like grounds Pool Tennis

Sag Harbor Suite by the Beach

8.8 out of 10, Excellent, (10)
"Trvis and Alice are great host and the property was a great place to stay close to the beach and downtown Sag Harbor."
Sag Harbor Suite by the 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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Other types of properties in Greenport you may be interested in

Sound View Greenport

4.0 star property
8.4 out of 10, Very good, (496)
"The view from the room"
The price is €210
includes taxes & fees
20 Jan - 21 Jan
Sound View Greenport

The Harbor Front Inn

3.5 star property
8.6 out of 10, Excellent, (428)
"Good "
The price is €197
includes taxes & fees
21 Jan - 22 Jan
The Harbor Front Inn

American Beech Hotel

3.5 star property
9.0 out of 10, Wonderful, (172)
"Wonderful Hotel ! Beautiful Room! Very clean and super comfortable!!! Awesome Staff !! Great Dinner at the restaurant too."
The price is €215
includes taxes & fees
19 Jan - 20 Jan
American Beech 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.

Frequently asked questions

Can I find a holiday rental in Greenport?

Yes, there are holiday rentals in Greenport close to Greenport Carousel, or you can select a more secluded 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 holiday rentals that Greenport has to offer?

Mid-Century Winter Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!: This holiday home rental outside Greenport is located on the beach, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Greenport?

With 94 Expedia holiday rentals, you're guaranteed 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 holiday rentals like in Greenport?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Greenport. Holiday rentals offer extras such as WiFi and washers and dryers to help you enjoy your stay. If you're concerned about a sanitised environment, a holiday rental can provide a sense of security away from shared hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for small groups.