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

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.2 out of 10, Wonderful, (24 reviews)
"Great stay & great staff!"
United States
James
The price is CA $474
CA $541 total
includes taxes & fees
Jul 8 - Jul 9
North Fork Resort

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (260 reviews)
"Beautiful property- we would definitely stay there again"
United States
Allison
The price is CA $638
CA $791 total
includes taxes & fees
Jul 5 - Jul 6
Cliffside Resort Condominiums

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.
The price is CA $579
CA $821 total
includes taxes & fees
Jul 12 - Jul 13
American Beech in Greenport - Petite King Room 7

Northfork Townhouse walk to all

Northfork Townhouse walk to all
Greenport
10.0 out of 10, Exceptional, (5 reviews)
"Great property located in a quiet neighborhood within walking distance to all in Greenport. The townhouse was clean and kitchen was well- appointed with off the street parking. Playground up the street was an added bonus with a old school merry-go-round! Would definitely stay again"
United States
Beth R.
The price is CA $524
CA $1,018 total
includes taxes & fees
Jun 25 - Jun 26
Northfork Townhouse walk to all

Beachfront Greenport Villa

Beachfront Greenport Villa
Greenport
9.8 out of 10, Exceptional, (13 reviews)
"yes the house had everything we needed"
United States
patricia m.
The price is CA $1,094
CA $1,816 total
includes taxes & fees
Jun 25 - Jun 26
Beachfront Greenport Villa

Renovated Townhouse walk to all

Renovated Townhouse walk to all
Greenport
9.4 out of 10, Exceptional, (12 reviews)
"The place was as advertised and in great walking distance to everything in town! "
United States
Liz H.
The price is CA $486
CA $969 total
includes taxes & fees
Jun 25 - Jun 26
Renovated Townhouse walk to all

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.
The price is CA $1,571
CA $2,513 total
includes taxes & fees
Jul 15 - Jul 16
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
The price is CA $382
CA $565 total
includes taxes & fees
Jun 29 - Jun 30
American Beech in Greenport - Deluxe King 6

Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (241 reviews)
"Very close to beach"
United States
Rabia
The price is CA $365
CA $463 total
includes taxes & fees
Jun 25 - Jun 26
Driftwood Resort

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
The price is CA $375
CA $467 total
includes taxes & fees
Jun 25 - Jun 26
Windward Shores Ocean Resort

Unit 1713: 1-Bedroom | 1st Floor-Ocean Front | Ocean Edge

Unit 1713: 1-Bedroom | 1st Floor-Ocean Front | Ocean Edge
Napeague
The price is CA $749
CA $1,315 total
includes taxes & fees
Jun 30 - Jul 1
Unit 1713: 1-Bedroom | 1st Floor-Ocean Front | Ocean Edge

Unit 1724: 1-Bedroom with Loft | 2nd Floor-Ocean Front Ocean View | Ocean Edge

Unit 1724: 1-Bedroom with Loft | 2nd Floor-Ocean Front Ocean View | Ocean Edge
Napeague
The price is CA $813
CA $1,406 total
includes taxes & fees
Jun 28 - Jun 29
Unit 1724: 1-Bedroom with Loft | 2nd Floor-Ocean Front Ocean View | Ocean Edge

Unit 1911: 1-Bedroom | 1st Floor-Dune View | Dunes West

Unit 1911: 1-Bedroom | 1st Floor-Dune View | Dunes West
Napeague
10.0 out of 10, Exceptional, (2 reviews)
"We love everything about this place. This was our 2nd time staying here and plan on coming back. The kitchen was redone and is beautiful. The location is perfect. It's close to the restaurants and shops in Montauk and Amagansett. The back deck is so roomy and comfortable. Sitting out there, listening to the ocean is heaven. We highly recommend this. "
United States
DiAnn E.
The price is CA $996
CA $1,659 total
includes taxes & fees
Jul 2 - Jul 3
Unit 1911: 1-Bedroom | 1st Floor-Dune View | Dunes West

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.
The price is CA $996
CA $1,659 total
includes taxes & fees
Jun 27 - Jun 28
Unit 1722: 1-Bedroom with Loft | 2nd Floor-Ocean Front Ocean View | Ocean Edge

Unit 611: Two-Bedroom | 1st Floor-Dune View | Periwinkle

Unit 611: Two-Bedroom | 1st Floor-Dune View | Periwinkle
Napeague
10.0 out of 10, Exceptional, (1 review)
The price is CA $1,626
CA $2,533 total
includes taxes & fees
Jul 19 - Jul 20
Unit 611: Two-Bedroom | 1st Floor-Dune View | Periwinkle

BlackBerry Private home with jacuzzi yearlong

BlackBerry Private home with jacuzzi yearlong
East Hampton
9.0 out of 10, Wonderful, (4 reviews)
"We had a great time staying here. The home is well worn and there are some fixtures that should be replaced "
United States
Suzanne R.
The price is CA $161
CA $1,419 total
includes taxes & fees
Jun 28 - Jun 29
BlackBerry Private home with jacuzzi yearlong

Spacious house in East Hampton with heated pool + WFH

Spacious house in East Hampton with heated pool + WFH
East Hampton
The price is CA $1,681
CA $2,880 total
includes taxes & fees
Jul 6 - Jul 7
Spacious house in East Hampton with heated pool + WFH

Brand New in the Heart of East Hampton Village with Pool

Brand New in the Heart of East Hampton Village with Pool
East Hampton
10.0 out of 10, Exceptional, (34 reviews)
"Great location and house was spotless! "
United States
Heather R.
The price is CA $3,127
CA $4,915 total
includes taxes & fees
Jul 12 - Jul 13
Brand New in the Heart of East Hampton Village with Pool

Beautiful home near Ocean Beach Park.

Beautiful home near Ocean Beach Park.
New London
10.0 out of 10, Exceptional, (19 reviews)
"A wonderful setting for a family, holiday gathering. Spacious, beautiful, spotless home. Lovely decorations, great views, fantastic kitchen, cozy gathering spaces, comfortable bedrooms, fun game room, and welcoming host."
United States
Martha F.
The price is CA $1,698
CA $3,063 total
includes taxes & fees
Jul 16 - Jul 17
Beautiful home near Ocean Beach Park.

Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
Waterford
10.0 out of 10, Exceptional, (12 reviews)
"We had a nice stay. Kitchen well stocked and house was clean and comfortable."
United States
Elaine A.
The price is CA $328
CA $763 total
includes taxes & fees
Jun 30 - Jul 1
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Greenport. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.