An aerial view of a harbor with boats, a ship, and a dock extending into the water.

Greenport Vacation Rentals

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Our top choices for Greenport vacation rentals

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (262 reviews)
"Beautiful property- we would definitely stay there again"
United States
Allison
$356 nightly
The price is $407
Jul 23 - Jul 24
Total with taxes and fees
Cliffside Resort Condominiums

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.2 out of 10, Wonderful, (25 reviews)
"Great stay & great staff!"
United States
James
$251 nightly
The price is $287
Jun 28 - Jun 29
Total with taxes and fees
North Fork Resort

American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.4 out of 10, Exceptional, (6 reviews)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
$492 nightly
The price is $562
Jul 5 - Jul 6
Total with taxes and fees
American Beech in Greenport - Petite King Room 7

New Construction Greenport Pool House - 3 Blocks from Town

New Construction Greenport Pool House - 3 Blocks from Town
Greenport
10.0 out of 10, Exceptional, (3 reviews)
"This was a great house for a large group! It was clean, and the backyard was perfect for our group to enjoy. The host was quick to respond to any questions we had. "
United States
Alexis P.
$1,536 nightly
The price is $1,755
Jul 15 - Jul 16
Total with taxes and fees
New Construction Greenport Pool House - 3 Blocks from Town

American Beech in Greenport - Deluxe King 6

American Beech in Greenport - Deluxe King 6
Greenport
2.0 out of 10, (1 review)
"Not as advertised. Very disappointed "
United States
Jeffrey
$348 nightly
The price is $398
Jun 29 - Jun 30
Total with taxes and fees
American Beech in Greenport - Deluxe King 6

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (46 reviews)
"We enjoyed our stay"
United States
JM B.
$244 nightly
The price is $276
Jul 1 - Jul 2
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (316 reviews)
"Nice homey room"
United States
Andrew
$500 nightly
The price is $571
Jun 28 - Jun 29
Total with taxes and fees
Windward Shores Ocean Resort

Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (241 reviews)
"Very close to beach"
United States
Rabia
$364 nightly
The price is $415
Jun 30 - Jul 1
Total with taxes and fees
Driftwood Resort

Adorable Cottage with Cottage porch, walk to water & town

Adorable Cottage with Cottage porch, walk to water & town
Westbrook Center
8.8 out of 10, Excellent, (6 reviews)
"Great host and property"
United States
Kevin K.
$643 nightly
The price is $727
Jul 24 - Jul 25
Total with taxes and fees
Adorable Cottage with Cottage porch, walk to water & town

The gardners Cottage 1 mile from long Island Sound - pet friendly

The gardners Cottage 1 mile from long Island Sound - pet friendly
Clinton
10.0 out of 10, Exceptional, (24 reviews)
"Enjoyed our stay - Highly recommend!"
United States
Mary S.
$443 nightly
The price is $502
Jul 1 - Jul 2
Total with taxes and fees
The gardners Cottage 1 mile from long Island Sound - pet friendly

Beach Cottage, private beach and pass

Beach Cottage, private beach and pass
East Lyme
10.0 out of 10, Exceptional, (13 reviews)
"An absolutely adorable and cozy cottage steps from a lovely beach. The location is great, beds were so comfortable and everything was clean and well designed. Would definitely stay here again"
United States
Maria M.
$581 nightly
The price is $657
Jul 6 - Jul 7
Total with taxes and fees
Beach Cottage, private beach and pass

Adorable Cottage, 5 min walk to water & town

Adorable Cottage, 5 min walk to water & town
Westbrook Center
9.4 out of 10, Exceptional, (15 reviews)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
$423 nightly
The price is $478
Jun 28 - Jun 29
Total with taxes and fees
Adorable Cottage, 5 min walk to water & town

Lovely studio with AC in charming Sag Harbor

Lovely studio with AC in charming Sag Harbor
Sag Harbor
$766 nightly
The price is $875
Jun 29 - Jun 30
Total with taxes and fees
Lovely studio with AC in charming Sag Harbor

Charming 2-bedroom house with WiFi, AC in lovely Waterford

Charming 2-bedroom house with WiFi, AC in lovely Waterford
Waterford
10.0 out of 10, Exceptional, (1 review)
"The home was very clean and welcoming."
United States
Michelle M.
$406 nightly
The price is $459
Jul 5 - Jul 6
Total with taxes and fees
Charming 2-bedroom house with WiFi, AC in lovely Waterford

Heart of Hamptons Retreat/Southampton/4 Bedrooms/Beaches/5 Star Restaurants

Heart of Hamptons Retreat/Southampton/4 Bedrooms/Beaches/5 Star Restaurants
Southampton
10.0 out of 10, Exceptional, (2 reviews)
"Had a great stay for a long weekend in the Hamptons. House was cozy and comfortable and in a good location."
United States
Beverly J.
$1,116 nightly
The price is $1,275
Jul 13 - Jul 14
Total with taxes and fees
Heart of Hamptons Retreat/Southampton/4 Bedrooms/Beaches/5 Star Restaurants

The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise
Old Lyme
9.0 out of 10, Wonderful, (4 reviews)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
United States
Lylian
$271 nightly
The price is $306
Jun 29 - Jun 30
Total with taxes and fees
The Stern at Soundview · Beach+Ocean+Sunrise

adorable ranch in beach community

adorable ranch in beach community
Old Saybrook
10.0 out of 10, Exceptional, (45 reviews)
"The experience was a pleasure - the house is comfy, and the location amazing! "
United States
Matthew V.
$743 nightly
The price is $841
Jul 15 - Jul 16
Total with taxes and fees
adorable ranch in beach community

Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
Old Saybrook Center
9.6 out of 10, Exceptional, (49 reviews)
"Lovely cottage! Enjoyed our stay! "
United States
Joyce S.
$694 nightly
The price is $785
Jul 12 - Jul 13
Total with taxes and fees
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

Cozy Lakefront Tiny House

Cozy Lakefront Tiny House
East Lyme
10.0 out of 10, Exceptional, (4 reviews)
"gorgeous tiny home on a tranquil lake!"
United States
Richard R.
$274 nightly
The price is $311
Jun 29 - Jun 30
Total with taxes and fees
Cozy Lakefront Tiny House

Unit 1722: 1-Bedroom with Loft | 2nd Floor-Ocean Front Ocean View | Ocean Edge

Unit 1722: 1-Bedroom with Loft | 2nd Floor-Ocean Front Ocean View | Ocean Edge
Napeague
10.0 out of 10, Exceptional, (2 reviews)
"First time in the area, and we hope to return. "
United States
Amy E.
$1,358 nightly
The price is $1,542
Jul 8 - Jul 9
Total with taxes and fees
Unit 1722: 1-Bedroom with Loft | 2nd Floor-Ocean Front Ocean View | Ocean Edge
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Greenport vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Greenport vacation 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 low season months. For more hustle and bustle, you may prefer to visit Greenport in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $276 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Greenport rentals

At Expedia, we put the best Greenport vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Greenport?

Yes, we give you a choice of vacation rentals in Greenport near Greenport Carousel, or you can select a more remote 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 vacation home rentals that Greenport has to offer?

Charming Two-Story Retreat in Southampton Village walk to town, beach and train.: This vacation home near Greenport offers a patio, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities like a dishwasher and a stovetop can make your vacation run smoothly.

How many vacation rentals are there in Greenport?

With 94 Expedia vacation rentals, you're sure 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 East End Seaport Maritime Museum and Railroad Museum of Long Island. While here, Greenport Carousel and Kontokosta Winery are other places worth a visit.

What are vacation rentals like in Greenport?

Vacation rentals are privately owned properties you can stay in for a couple days or more in Greenport. Vacation rentals feature amenities like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about a sanitized environment, vacation rentals can offer a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for a family getaway.