Greenport Vacation Rentals
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Our top choices for Greenport vacation rentals
1. Cliffside Resort Condominiums
Cliffside Resort CondominiumsGreenport
9.0 out of 10, Wonderful, (299 reviews)
"Great condo. Very nice location and grounds."
William
The price is CA $243
CA $434 total
includes taxes & fees
Nov 30 - Dec 1
2. Harbor Heights
Harbor HeightsPipes Cove
10.0 out of 10, Exceptional, (28 reviews)
"Perfect spot to stay on the North Fork!"
Steven R.
The price is CA $121
CA $324 total
includes taxes & fees
Nov 9 - Nov 10
3. The SandPiper
The SandPiperPipes Cove
9.6 out of 10, Exceptional, (57 reviews)
"Place was perfect ! Great location / clean/ everything we needed was there ! Would love to stay there again :)"
Manuela C.
The price is CA $121
CA $324 total
includes taxes & fees
Nov 10 - Nov 11
4. Aqua Vista
Aqua VistaPipes Cove
10.0 out of 10, Exceptional, (52 reviews)
"Great location and nice spot."
Kerri L.
The price is CA $134
CA $341 total
includes taxes & fees
Nov 9 - Nov 10
5. North Fork Resort
North Fork ResortGreenport
9.6 out of 10, Exceptional, (73 reviews)
"Everything was perfect 💞"
Altynai
The price is CA $440
CA $503 total
includes taxes & fees
Nov 9 - Nov 10
6. Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + OfficePipes Cove
10.0 out of 10, Exceptional, (35 reviews)
"We had a great stay!! "
Callie E.
The price is CA $184
CA $492 total
includes taxes & fees
Nov 9 - Nov 10
7. American Beech in Greenport - Petite King Room 7
American Beech in Greenport - Petite King Room 7Greenport
9.4 out of 10, Exceptional, (6 reviews)
"Great place! So nice."
Paul F.
The price is CA $281
CA $410 total
includes taxes & fees
Nov 9 - Nov 10
8. Beach Block Hideaway
Beach Block HideawayPipes Cove
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful 2 bedroom close to town. The house is well kept we would rent here again."
Teresa C.
The price is CA $276
CA $605 total
includes taxes & fees
Nov 11 - Nov 12
9. Northfork Townhouse walk to all
Northfork Townhouse walk to allGreenport
9.4 out of 10, Exceptional, (9 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"
Beth R.
The price is CA $356
CA $797 total
includes taxes & fees
Nov 11 - Nov 12
10. Renovated Townhouse walk to all
Renovated Townhouse walk to allGreenport
9.6 out of 10, Exceptional, (15 reviews)
"The place was as advertised and in great walking distance to everything in town! "
Liz H.
The price is CA $324
CA $756 total
includes taxes & fees
Nov 10 - Nov 11
11. 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 TownGreenport
10.0 out of 10, Exceptional, (1 review)
"Wonderful house. Immaculate with all the provisions you can hope for. Perfect location and beautifully done!"
Jeannette M.
The price is CA $677
CA $1,186 total
includes taxes & fees
Nov 18 - Nov 19
12. Beachfront Greenport Villa
Beachfront Greenport VillaGreenport
9.6 out of 10, Exceptional, (15 reviews)
"Beautiful home, great views and host!"
Kate R.
The price is CA $725
CA $1,328 total
includes taxes & fees
Nov 11 - Nov 12
13. American Beech in Greenport - Deluxe King 6
American Beech in Greenport - Deluxe King 6Greenport
2.0 out of 10, (1 review)
"Not as advertised. Very disappointed "
Jeffrey
The price is CA $324
CA $463 total
includes taxes & fees
Nov 9 - Nov 10
14. Windward Shores Ocean Resort
Windward Shores Ocean ResortNapeague
8.8 out of 10, Excellent, (333 reviews)
"Omg so peaceful and beautiful. Felt like I was in paradise. My fiancee and I enjoyed every moment except checking out because we did not want to leave. Such beauty it was worth the 3 hour car ride. Perfect getaway.💜🙏"
Banessa
The price is CA $186
CA $251 total
includes taxes & fees
Nov 9 - Nov 10
15. North Fork Grinch Getaway & Hot Chocolate Bar. Two Bedroom Sleeps 4.
North Fork Grinch Getaway & Hot Chocolate Bar. Two Bedroom Sleeps 4.Southold
9.6 out of 10, Exceptional, (10 reviews)
"Overall we had a great stay, we weren’t in the apartment much and really only needed it for a place to stay at night. The space is the basement of a home with little natural sunlight. Overall it was ok for a weekend stay."
Kelly V.
The price is CA $353
CA $668 total
includes taxes & fees
Nov 9 - Nov 10
16. 1-bedroom cottage with Grove Beach 🏖️ access.
1-bedroom cottage with Grove Beach 🏖️ access.Clinton
9.8 out of 10, Exceptional, (66 reviews)
"Cozy vrbo with a great location to the beach, outlets shops and excellent restaurants!"
Marcy C.
The price is CA $186
CA $320 total
includes taxes & fees
Nov 10 - Nov 11
17. Charming Accommodations in the Hamptons
Charming Accommodations in the HamptonsSag Harbor
The price is CA $318
CA $668 total
includes taxes & fees
Nov 9 - Nov 10
18. Year round Jacuzzi - Blackberry East Hampton Home
Year round Jacuzzi - Blackberry East Hampton HomeEast Hampton
9.2 out of 10, Wonderful, (7 reviews)
"We had a great time staying here. The home is well worn and there are some fixtures that should be replaced "
Suzanne R.
The price is CA $136
CA $1,954 total
includes taxes & fees
Nov 10 - Nov 11
19. Steps to the beach | Seabreeze Cottage #3
Steps to the beach | Seabreeze Cottage #3Hampton Bays
6.0 out of 10, (3 reviews)
"The property needs a major cleaning and repairs. The floors were sticky, and the carpet was dirty. Furniture was dirty and soiled. There was dried food on the utensils.
The pipes groaned at all hours, several times an hour. The bed creaked with every movement. Bedroom blinds were broken and wouldn’t close all the way. The bedside lamp on the wall was falling off.
The last straw was the huge spider that jumped down from the closet onto me.
We ended up leaving after less than 24 hours and...
Lydia
The price is CA $85
CA $642 total
includes taxes & fees
Nov 15 - Nov 16
20. The Stern at Soundview · Beach+Ocean+Sunrise
The Stern at Soundview · Beach+Ocean+SunriseOld Lyme
8.4 out of 10, Very good, (6 reviews)
"If you are looking for a place to sleep, this place is ok. No place to sit down or put anything down. Just a bed and an old beat up tiny side table. Refrigerator is tiny, needed to be cleaned and defrosted. Stains in the bathroom ceiling tiles and the smell of Marijuana at night. Hot plate and microwave present but did not use. The entryway and stairs were dirty and could use a coat of paint and trim. The beach was the highlight and a very short walk. Definitely not worth the $$$ we paid."
Janine
The price is CA $178
CA $349 total
includes taxes & fees
Nov 9 - Nov 10
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
Saybrook Point Resort & Marina
10/10 Excellent
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.
