Greenport Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Sep 24 - Sep 25
Tomorrow
Sep 25 - Sep 26
This weekend
Sep 26 - Sep 28
Next weekend
Oct 3 - Oct 5

Vacation Rentals in Greenport

Cliffside Resort Condominiums
Beach nearby

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (240)
"Great view of the water and nice amenities with the beach and pool."
The price is ￥46,711
￥59,782 total
includes taxes & fees
Oct 2 - Oct 3
Cliffside Resort Condominiums
'The Gate House'on Beach front Estate with Dockage. Walk to Village .
On the beach

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

9.8 out of 10, Exceptional, (97)
"My husband and I brought our puppy. He had a great time running around the yard and beach. We enjoyed our stay and hope to return. The property is beautiful and we were very happy to find a pet friendly place on the water and close to town."
'The Gate House'on Beach front Estate with Dockage. Walk to Village .
NEW VICTORIAN GEM IN GREENPORT
Outdoor pool

NEW VICTORIAN GEM IN GREENPORT

10.0 out of 10, Exceptional, (11)
"We had a great stay! Clean property and well maintained. The hosts were very friendly, helpful and welcoming. Would go back and recommend to others!"
NEW VICTORIAN GEM IN GREENPORT
Windward Shores Ocean Resort
Ocean View 2BD Corner King and Queen | Living area | TV

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (295)
"Very nice & affordable "
The price is ￥19,449
￥25,432 total
includes taxes & fees
Oct 19 - Oct 20
Windward Shores Ocean Resort
Driftwood Resort
Apartment, 1 Bedroom | Private kitchen | Fridge, microwave, cookware/dishes/utensils

Driftwood Resort

3.5 star property
9.0 out of 10, Wonderful, (232)
"Great place to stay for small family "
The price is ￥20,421
￥28,143 total
includes taxes & fees
Sep 29 - Sep 30
Driftwood Resort
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
Outdoor pool, a heated pool

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

2.5 star property
9.6 out of 10, Exceptional, (15)
"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 ￥25,906
￥59,954 total
includes taxes & fees
Oct 1 - Oct 2
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Outdoor pool, a heated pool

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

9.8 out of 10, Exceptional, (31)
"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
Fairy Tale Guest Cottage in Magic Garden by Pool
Property grounds

Fairy Tale Guest Cottage in Magic Garden by Pool

10.0 out of 10, Exceptional, (74)
"We had an AMAZING stay at Eunyoung and Mark's magical cottage. The property was exactly as described. Eunyoung and Mark are delightful people. Tranquil, quiet, peaceful. "
Fairy Tale Guest Cottage in Magic Garden by Pool
The Stern at Soundview · Beach+Ocean+Sunrise
On the beach

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 ￥9,701
￥26,794 total
includes taxes & fees
Oct 7 - Oct 8
The Stern at Soundview · Beach+Ocean+Sunrise
Southampton cozy cottage by the beach
Beach

Southampton cozy cottage by the beach

10.0 out of 10, Exceptional, (1)
"Great stay. Would stay again. "
Southampton cozy cottage by the beach
Rustic Lakeside Cabin at White Gate Farm
Interior

Rustic Lakeside Cabin at White Gate Farm

10.0 out of 10, Exceptional, (119)
"Just amazing!"
Rustic Lakeside Cabin at White Gate Farm
Cozy houseboat escape surrounded by breath taking views across from Rocky Neck!
Terrace/patio

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

10.0 out of 10, Exceptional, (13)
"Such a fun, beautiful and unique stay. Would love to stay again!"
The price is ￥29,522
￥49,597 total
includes taxes & fees
Sep 25 - Sep 26
Cozy houseboat escape surrounded by breath taking views across from Rocky Neck!
10 Bedroom Hampton House with a regulation size Pickleball court
Pool

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

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.
Shoreline Oasis
Exterior

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 ￥26,422
￥38,762 total
includes taxes & fees
Sep 25 - Sep 26
Shoreline Oasis
Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food
Outdoor pool

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

10.0 out of 10, Exceptional, (102)
"Our multigenerational long weekend loved our stay. Fab manager. House so well kitted out. "
Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food
Safari Tent Glamping,S6-CedarPt, East Hampton, NY
Terrace/patio

Safari Tent Glamping,S6-CedarPt, East Hampton, NY

8.8 out of 10, Excellent, (3)
"We loved the surroundings, the pizza restaurant with live music and ping pong, and the friendly, warm atmosphere and kind staff. We do wish the bathrooms and especially the showers were cleaner."
The price is ￥29,857
￥39,003 total
includes taxes & fees
Oct 3 - Oct 4
Safari Tent Glamping,S6-CedarPt, East Hampton, NY
The Mast at Soundview · Beach+Ocean+Sunrise
On the beach

The Mast at Soundview · Beach+Ocean+Sunrise

2.0 star property
9.4 out of 10, Exceptional, (3)
"Nice place, little smaller than I was expecting, but location was close to the beach, info regarding access to the property was clear and easy to follow! Parking was assigned but other occupants decided not to utilize their assigned space and took ours. Be prepared to clean the studio before you leave to include dishes and take out the trash. Was surprised by the cleaning request. Overall great weekend!"
The price is ￥9,701
￥26,794 total
includes taxes & fees
Oct 6 - Oct 7
The Mast at Soundview · Beach+Ocean+Sunrise
Freeboard at Soundview · Beach+Ocean+Sunrise
On the beach

Freeboard at Soundview · Beach+Ocean+Sunrise

2.0 star property
9.2 out of 10, Wonderful, (5)
"It was very close to the beach , quiet, parking on property room had everything you would need i enjoyed my stay didnt want to leave so soon wouldve liked at least 1 more day maybe next year thank you. "
The price is ￥8,942
￥25,926 total
includes taxes & fees
Oct 7 - Oct 8
Freeboard at Soundview · Beach+Ocean+Sunrise
Large 6-Bedroom 3-BR Waterfront Hamptons House, your own Private Beach in Front.
TV, fireplace

Large 6-Bedroom 3-BR Waterfront Hamptons House, your own Private Beach in Front.

The price is ￥82,071
￥434,596 total
includes taxes & fees
Oct 12 - Oct 13
Large 6-Bedroom 3-BR Waterfront Hamptons House, your own Private Beach in Front.
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Greenport Hotel Reviews

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

10/10 Excellent
"Highly recommend!"
Christina 1-night trip
Posted 2 days ago
Pier Blue Inn Old Saybrook - Essex

Find out more about Greenport

Find out more about Greenport

Search for holiday rentals in Greenport on Expedia! You can easily find your home rentals, villas, holiday apartments in Greenport using one of the methods below:

  • View our selection of featured holiday rentals in Greenport
  • Use the map to find apartments and other holiday homes in the Greenport neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Greenport while they last

Look no further and take a look at our great range of rental properties in Greenport!

Explore a world of travel with Expedia

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?

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor : This vacation home rental near Greenport offers an outdoor pool, a fireplace, and a barbecue grill 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 a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Greenport?

With 97 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 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 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.