Greenport Vacation Rentals

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Our top choices for Greenport vacation rentals

North Fork Cottages & RV Resort

North Fork Cottages & RV Resort
3.0 star property
Greenport
8.8 out of 10, Excellent, (13 reviews)
"great place to stay, clean and quiet....loved it"
United States
Darlin
The price is CA $379
CA $433 total
includes taxes & fees
May 26 - May 27
North Fork Cottages & RV Resort

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (252 reviews)
"Convenient parking and proximity to all."
United States
Rosemaria
The price is CA $229
CA $321 total
includes taxes & fees
May 11 - May 12
Cliffside Resort Condominiums

American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.2 out of 10, Wonderful, (5 reviews)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
The price is CA $286
CA $436 total
includes taxes & fees
May 11 - May 12
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 $443
CA $899 total
includes taxes & fees
May 11 - May 12
Northfork Townhouse walk to all

The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
Greenport
10.0 out of 10, Exceptional, (1 review)
"Wonderful house. Immaculate with all the provisions you can hope for. Perfect location and beautifully done!"
United States
Jeannette M.
The price is CA $793
CA $1,370 total
includes taxes & fees
May 27 - May 28
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

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 $1,196
CA $1,964 total
includes taxes & fees
May 27 - May 28
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 $341
CA $505 total
includes taxes & fees
May 10 - May 11
American Beech in Greenport - Deluxe King 6

Cozy Lakefront Tiny House

Cozy Lakefront Tiny House
East Lyme
10.0 out of 10, Exceptional, (3 reviews)
"It was a peaceful and quant "
United States
Patricia M.
The price is CA $169
CA $347 total
includes taxes & fees
May 10 - May 11
Cozy Lakefront Tiny House

Lakefront Boho Tiny House

Lakefront Boho Tiny House
East Lyme
10.0 out of 10, Exceptional, (4 reviews)
"Every thing was amazing "
United States
Annaliaa C.
The price is CA $167
CA $346 total
includes taxes & fees
May 11 - May 12
Lakefront Boho Tiny House

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

Safari Tent Glamping,S5-CedarPt, East Hampton, NY
East Hampton
8.6 out of 10, Excellent, (4 reviews)
"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."
United States
Jennifer
The price is CA $294
CA $445 total
includes taxes & fees
May 25 - May 26
Safari Tent Glamping,S5-CedarPt, East Hampton, NY

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (312 reviews)
"We always stay at the Windward Shores when we go to Montauk. It is a beautiful, clean and comfortable place, and the price is great!"
United States
Joseph
The price is CA $218
CA $286 total
includes taxes & fees
May 20 - May 21
Windward Shores Ocean Resort

Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (237 reviews)
"Wonderful location, right on the beach. The staff was kind and welcoming. The property was beautiful with a pool, playground, tennis and basketball courts, cornhole, etc. Very family friendly. Some walkable restaurants nearby and a quick 5-10 minute drive into town where a lot of the restaurants and shops are. We did have ants all in our food one day but the staff addressed it quickly "
United States
John
The price is CA $213
CA $288 total
includes taxes & fees
May 20 - May 21
Driftwood Resort

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

Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
Waterford
10.0 out of 10, Exceptional, (22 reviews)
"The home was exactly as described and well appointed, yet charming and cozy. Great location near Niantic, Stonington and Mystic. Perfect for a sister’s birthday getaway. "
United States
Dianne B.
The price is CA $234
CA $475 total
includes taxes & fees
May 14 - May 15
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

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, (11 reviews)
"Beautiful home, we enjoyed our stay. Clean, modern and had everything there we needed. Host was very attentive to our needs and was quick to respond. Looking forward to spend another long weekend there. Highly recommend!"
United States
Brenda W.
The price is CA $208
CA $594 total
includes taxes & fees
May 12 - May 13
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise
Old Lyme
10.0 out of 10, Exceptional, (3 reviews)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
United States
Lylian
The price is CA $182
CA $366 total
includes taxes & fees
May 10 - May 11
The Stern at Soundview · Beach+Ocean+Sunrise

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.
The price is CA $219
CA $521 total
includes taxes & fees
May 12 - May 13
Charming 2-bedroom house with WiFi, AC in lovely Waterford

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

Safari Tent Glamping,S10-CedarPt, East Hampton, NY
East Hampton
The price is CA $294
CA $445 total
includes taxes & fees
May 25 - May 26
Safari Tent Glamping,S10-CedarPt, East Hampton, NY

Insta-worthy Couples Retreat: Perfect for romantic getaway!

Insta-worthy Couples Retreat: Perfect for romantic getaway!
Old Lyme
9.4 out of 10, Exceptional, (56 reviews)
"Adorable cottage. Nice location. "
United States
Janet B.
The price is CA $154
CA $371 total
includes taxes & fees
May 20 - May 21
Insta-worthy Couples Retreat: Perfect for romantic getaway!

Seabreeze 4 Charming Cottage walk to US Open

Seabreeze 4 Charming Cottage walk to US Open
Hampton Bays
8.8 out of 10, Excellent, (3 reviews)
"Great stay. Would stay again. "
United States
Weston B.
The price is CA $108
CA $621 total
includes taxes & fees
May 10 - May 11
Seabreeze 4 Charming Cottage walk to US Open

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (41 reviews)
"We had such a wonderful one night stay at Shalom Cottage! The place was absolutely beautiful—so cozy, clean, and thoughtfully decorated. Raj, the host was truly amazing! He was kind, responsive, and made sure we had everything we needed from start to finish. We felt so welcomed and comfortable the entire time. We would definitely love to stay here again and highly recommend it to anyone! "
United States
Alexis F.
The price is CA $142
CA $286 total
includes taxes & fees
May 17 - May 18
1-bedroom cottage with Grove Beach 🏖️ access.
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?

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping: This vacation home rental near Greenport offers an outdoor pool, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Greenport?

With 95 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.