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Holiday Rentals in Greenport

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Holiday Rentals in Greenport

Cliffside Resort Condominiums

3.0 star property
Greenport
9.0 out of 10, Wonderful, (248)
"Great stay - beautiful place"
United States
Rebecca
Cliffside Resort Condominiums

Large Charming Historic House close to Beaches

Clinton
9.8 out of 10, Exceptional, (34)
"Great place and location. There was 8 of us and plenty of space and beds!"
United States
Sandy B.
Large Charming Historic House close to Beaches

Driftwood Resort

3.5 star property
Montauk
9.0 out of 10, Wonderful, (236)
"Great place to stay for small family "
United States
DongHo
Driftwood Resort

Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available

Sag Harbor
10.0 out of 10, Exceptional, (89)
"House that has everything you need for a wonderful getaway! Excellent communication with the property owner. Thank you Jay for everything and your hospitality! "
United States
Maria R.
Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available

1-bedroom cottage with Grove Beach 🏖️ access.

Clinton
9.2 out of 10, Wonderful, (36)
"Cottage itself clean, but sewage smell in bathroom. Surrounding property derelict motel with ongoing consruction. "
United States
michelle
The price is €160
includes taxes & fees
1 Dec - 2 Dec
1-bedroom cottage with Grove Beach 🏖️ access.

Mid-Century Home with Pool, Private Beach Access, and Long-Stay Summer Savings

East Hampton
10.0 out of 10, Exceptional, (95)
"Awesome location. Very comfortable stay. Had everything we needed. Would definitely stay here again"
United States
Irish T.
Mid-Century Home with Pool, Private Beach Access, and Long-Stay Summer Savings

Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

2.0 star property
Waterford
10.0 out of 10, Exceptional, (13)
"The property was amazing. The house was very clean and the game room was really fun. It was a very cute place and the backyard was perfect for sitting outside in the afternoon. The beds were really soft and comfortable as well."
United States
Jorie M.
The price is €311
includes taxes & fees
2 Dec - 3 Dec
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn

Madison
10.0 out of 10, Exceptional, (36)
"We had a wonderful time here!! "
United States
Leslie S.
Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn

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

East Lyme
10.0 out of 10, Exceptional, (106)
"White Gate Farm was a fantastic place for my large family to come together. Close to home, yet felt like we were in the Vermont countryside. Great host and clean and well equipped property."
United States
Catherine B.
Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food

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

Hampton Bays
9.6 out of 10, Exceptional, (143)
"Large house and deck with plenty of room Beautiful view of bay Not easy to get from deck to water because of boulders "
United States
Robert H.
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

The Stern at Soundview · Beach+Ocean+Sunrise

2.0 star property
Old Lyme
10.0 out of 10, Exceptional, (3)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
United States
Lylian
The price is €172
includes taxes & fees
7 Dec - 8 Dec
The Stern at Soundview · Beach+Ocean+Sunrise

Rustic Lakeside Cabin at White Gate Farm

East Lyme
10.0 out of 10, Exceptional, (123)
"5-star lake view. Amazing stay. we absolutely enjoyed visiting this farm every year. "
United States
Mariya S.
Rustic Lakeside Cabin at White Gate Farm

Waterfront Beach House

Clinton
9.6 out of 10, Exceptional, (54)
"This was our third year spending an amazing beach week at this lovely property! Thanks again for the perfect week and see you again next year!"
United States
Tim S.
Waterfront Beach House

Stunning Hampton Holiday Family Fantasy for your Team

East Hampton
9.8 out of 10, Exceptional, (74)
"We had an incredible stay! The property was as advertised. Very easy in and out and stocked with all the essentials to cook, hangout, use the pool or have a movie night. Our host was very responsive throughout the weekend and gave great recommendations. Highly recommend. "
United States
Henry S.
Stunning Hampton Holiday Family Fantasy for your Team

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

Southampton
9.8 out of 10, Exceptional, (32)
"This place was so nice and so close to so many fun places! "
United States
Daniella L.
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

The Bridge at Soundview · Beach+OceanView+Sunrise

2.0 star property
Old Lyme
10.0 out of 10, Exceptional, (1)
"The space was much larger than expected and was perfect for a group of 4 adults and 3 kids under 3! We had a great time, being a 5 minute walk from the beach and having a comfortable space to come back to. We'll definitely be coming back."
United States
Emotional J.
The price is €436
includes taxes & fees
25 Nov - 26 Nov
The Bridge at Soundview · Beach+OceanView+Sunrise

10 Bedroom Hampton House with a regulation size Pickleball court

Hampton Bays
10.0 out of 10, Exceptional, (32)
"Wonderful place to stay, close and convenient to restaurants/bars. Very comfortable and cool space with games and eclectic decorations "
United States
Chris M.
10 Bedroom Hampton House with a regulation size Pickleball court

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

Old Saybrook
10.0 out of 10, Exceptional, (34)
"Enjoyed our stay"
United States
Nicole L.
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

Charming 4-bedroom house with salt water pool, AC and WiFi in Hampton Bays

Hampton Bays
10.0 out of 10, Exceptional, (1)
"Awesome house, very convenient to the beach and town. Beautiful yard and pool for grilling and hanging. Would love to come back again!"
United States
Brendan O.
Charming 4-bedroom house with salt water pool, AC and WiFi in Hampton Bays

Shoreline Oasis

Clinton
9.2 out of 10, Wonderful, (7)
"Everything was as advertised or better. Lovely quiet area near beautiful beaches and great restaurants. We had a terrific experience. "
United States
Tom S.
The price is €230
includes taxes & fees
25 Nov - 26 Nov
Shoreline Oasis
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

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, apart-hotels, 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 favorite 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 depends 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 €172 per night. Entering your travel dates in the search wizard you might find 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.

How many holiday rentals are there in Greenport?

With 98 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.