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Greenport Holiday Rentals

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Holiday Rentals in Greenport

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (239)
"Had a great time. Will be back"
The price is AU$644
includes taxes & fees
11 Sept - 12 Sept
Cliffside Resort Condominiums

'The Gate House'on Beach front Estate with Dockage. Walk to Village .

9.8 out of 10, Exceptional, (97)
"This is a great place to stay in Greenport. It has a private beach and is quiet and friendly. It's a 2-minute drive to town and shops, but you will want to spend your time enjoying the beautiful waterfront views."
'The Gate House'on Beach front Estate with Dockage. Walk to Village .

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (293)
"Very nice & affordable "
The price is AU$264
includes taxes & fees
29 Sept - 30 Sept
Windward Shores Ocean Resort

Driftwood Resort

3.5 star property
9.0 out of 10, Wonderful, (231)
"Great place to stay for small family "
The price is AU$351
includes taxes & fees
25 Sept - 26 Sept
Driftwood Resort

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

2.5 star property
9.6 out of 10, Exceptional, (13)
"Tucked away in a quiet residential area. Rooms were clean and kitchenette was well equipped. Private parking spot in the driveway next to the cottage was a bonus. Highly recommended!"
The price is AU$626
includes taxes & fees
8 Sept - 9 Sept
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

Fairy Tale Guest Cottage in Magic Garden by Pool

10.0 out of 10, Exceptional, (72)
"In the Hamptons working a Vintage market so I barely got to enjoy this incredibly gorgeous home, but it was perfect for just me and the host were absolutely delightful so friendly and accommodating they even let me sleep in which I haven’t had a chance to do in sometime so that was much appreciated I rested better than I have in months in this sweet cottage on a beautiful property. They made sure I was taken care of while giving me speciation enjoy some much needed quiet time. It’s a stunning...
Fairy Tale Guest Cottage in Magic Garden by Pool

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

10.0 out of 10, Exceptional, (29)
"Our trip was amazing, the pool was in perfect condition and the house had everything we needed. Would definitely stay here again!!"
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

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

10.0 out of 10, Exceptional, (94)
"Property was great! Rick was super responsive. It was a great trip to the Hamptons! "
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

The Stern at Soundview · Beach+Ocean+Sunrise

2.0 star property
10.0 out of 10, Exceptional, (3)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
The price is AU$275
includes taxes & fees
8 Sept - 9 Sept
The Stern at Soundview · Beach+Ocean+Sunrise

Rustic Lakeside Cabin at White Gate Farm

10.0 out of 10, Exceptional, (116)
"Just amazing!"
Rustic Lakeside Cabin at White Gate Farm

Cozy houseboat escape surrounded by breath taking views across from Rocky Neck!

10.0 out of 10, Exceptional, (12)
"Such a fun, beautiful and unique stay. Would love to stay again!"
The price is AU$569
includes taxes & fees
1 Oct - 2 Oct
Cozy houseboat escape surrounded by breath taking views across from Rocky Neck!

Shoreline Oasis

9.2 out of 10, Wonderful, (7)
"A very comfortable, clean, convenient apartment close to the shore and all the natural attractions near Madison and Clinton. We particularly appreciated that the owners quickly replaced the bedroom air conditioner when it broke. Great hosts!"
The price is AU$405
includes taxes & fees
8 Sept - 9 Sept
Shoreline Oasis

Mansion Near the Bay. 7 bedrooms! Chef’s kitchen.

9.8 out of 10, Exceptional, (53)
"Our family (16) spent a week at the property and found the house and property in good order, comfortable and convenient to the bay and other attractions. I would definitely recommend it as a great family vacation."
Mansion Near the Bay. 7 bedrooms! Chef’s kitchen.

Stunning Southampton Village Modern Home

The price is AU$26,665
includes taxes & fees
8 Sept - 9 Sept
Stunning Southampton Village Modern Home

Southampton cozy cottage by the beach

10.0 out of 10, Exceptional, (1)
"Great stay. Would stay again. "
Southampton cozy cottage by the beach

Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food

10.0 out of 10, Exceptional, (99)
"Our multigenerational long weekend loved our stay. Fab manager. House so well kitted out. "
The price is AU$2,976
includes taxes & fees
11 Sept - 12 Sept
Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food

10 Bedroom Hampton House with a regulation size Pickleball court

10.0 out of 10, Exceptional, (32)
"Had so much fun this weekend in Hampton Bays! House was perfect for a group of friends - many bedrooms, bathrooms, great pool with tons of outdoor games, and even the arcade room inside! So close to the beach, and a number of great restaurants. Highly recommend this house, and appreciate how helpful our host was with making sure we had everything we need and more!"
10 Bedroom Hampton House with a regulation size Pickleball court

Safari Tent Glamping,S5-CedarPt, East Hampton, NY

8.0 out of 10, Very good, (3)
"We loved our tent, the view was great. The bed was super comfortable. We will definitely come back and hopefully stay longer. Also, the pizza is so good as was the watermelon Margherita."
The price is AU$452
includes taxes & fees
14 Sept - 15 Sept
Safari Tent Glamping,S5-CedarPt, East Hampton, NY

Safari Tent Glamping,S10-CedarPt, East Hampton, NY

The price is AU$452
includes taxes & fees
14 Sept - 15 Sept
Safari Tent Glamping,S10-CedarPt, East Hampton, NY

Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

9.6 out of 10, Exceptional, (134)
"Perfect property to hangout and stay entertained for hours"
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
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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Top Greenport Hotel Reviews

Find out more about Greenport

Find out more about Greenport

Everything you need to know about Greenport holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Greenport holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Greenport holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Greenport holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Greenport. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Greenport holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Greenport holiday rentals we have selected for you start as low as AU$264 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Greenport rentals

At Expedia, we put the best Greenport holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Greenport rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Greenport holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Greenport. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor : This holiday home rental outside of Greenport offers an outdoor pool, a fireplace and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. It offers a patio, a garden and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Greenport?

With 97 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.