Greenport vacation rentals
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Top-rated vacation rentals in Greenport
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
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Popular amenities for Greenport vacation rentals
Greenport apartment rentals
Apartment in North Fork
4.82 out of 5 average rating, 119 reviewsHouse on First
Incredible location! Walking distance to the town. The neighborhood is very quiet and we felt very comfortable all weekend long. Carole and Rich are wondering hosts, and the apartment had everything we needed. We would recommend!!
Apartment in Westhampton Beach
4.94 out of 5 average rating, 105 reviewsNEW, steps to the village 1 mile to Dune Road
Susan's apt is in a convenient part of Westhampton Beach. Minutes from farmer's market and Main street. Longer walk but perfectly doable 25min to Rogers beach. The apt is nicely decorated and well equipped. Susan and her husband were friendly and explained to me how to set the internet and temperature in the apt. I enjoyed staying there and hope to return in the future.
Apartment in North Fork
4.96 out of 5 average rating, 142 reviewsUpscale Newly Constructed Apartment
Our 3 time staying at Amanda’s home. Beautiful and spacious within walking distance to village. Looking forward to coming back next year!
Apartment in Shelter Island Heights
4.91 out of 5 average rating, 245 reviewsSquire Chase House
Great spot! Very walkable. It's also a great layout if traveling with small children - there is a separate meditation room upstairs that was perfect for setting up our travel cribs. Would stay again!
Apartment in Southampton
4.87 out of 5 average rating, 127 reviewsSouthampton Village Studio
Michael is such a courteous, considerate and generous host. We have stayed many, many times and it feels like a second home. I highly recommend this cozy, clean apartment. Micheal goes out of his way to make sure you are taken care of. Best host! Truly!
Apartment in Sag Harbor
4.92 out of 5 average rating, 146 reviewsWhaling Captain Pierson's Apartment TOO
My husband and I thoroughly enjoyed our stay in Sag Harbor at Whaling Captain Pierson's Apartment TOO! The apartment was absolutely beautiful and the surroundings were gorgeous. My husband and I are a lover of old / historic homes and antiques, and if you are too - this is a great place for you. We stayed in Sag Harbor for our anniversary weekend and Paris made us feel right at home, and went as far as to leave us a wonderful gift to help us celebrate. Would highly recommend to others! We hope to be back.
Apartment in North Fork
4.97 out of 5 average rating, 239 reviewsGreenport Village View - Walk Downtown 2BR/1BA
Danielle was an excellent host, the place is wonderful and in an excellent location. We are hoping we can find it again in the summer but expect it to sell out! :) Thank you for the hospitality!
Apartment in Sag Harbor
4.89 out of 5 average rating, 154 reviewsSag Harbor Village Oasis
I had the best stay, it’s about 15 min. Or a little more if you’re not in a hurry to down town Sag Harbor and all the super cute shops and wonderful restaurants… and of course all the Galleries… Such a cute place and the bed was overly comfy… The host was so accommodating and helpful, I definitely recommend this place!!!
Other great vacation rentals in Greenport
Cottage in North Fork
5 out of 5 average rating, 12 reviewsLovely North Fork Beach Cottage (2 BR/2 bath)!
The Cottage was a perfect blend of rustic and modern, thoughtfully appointed and had everything we could think of. Our big plus was the trust and no hassle from the hosts to include our beloved big dog. My husband and I came out to the North Fork for our October babymoon. The Cottage town area is very serene during the fall season, with most activity around the pumpkin farms. Our favorite things to do—take the dog down to the bulkhead in the mornings, spend the afternoons on a nature walk/winery nearby and nights at a local restaurant. Cons but not dealbreakers: Spotty internet often went in/out. Persistent fruit flies all throughout house, traps didn’t help. The listing advises of the Main House rental, we found it not very private to the closeby Cottage. With big glass doors and sheer curtains, you’re in plain view to the House at night. It felt too intimate for our preference to share the small beach with strangers 15 ft away, esp with their kids and our dog.
Cottage in Guilford
4.99 out of 5 average rating, 128 reviews"Red House on the Knoll" at Indian Cove
We had a wonderful stay at Gail's house! We were welcomed with snacks and essentials in the fridge and delicious homemade toffee : )The house is beautiful and spacious with plenty of room for guests to hang out in various areas, kids and dogs included. We loved our time here while visiting family and would love to stay again!
Home in Hampton Bays
4.9 out of 5 average rating, 92 reviewsPrivate Home minutes from Beach and Nightlife
Perfect weekend getaway spot with a wonderful backyard. The hot tub was a treat and the rooms were clean and spacious. Highly recommend!
Home in Sag Harbor
5 out of 5 average rating, 11 reviewsDelightful Sag Harbor Home w Pool
I spent the weekend at Eric's house with my parents and it was absolutely perfect. Such a bright, comfortable house in an incredibly convenient location. ~5 minute drive to Sag Harbor town, ~15 minute drive to Sagg Main beach, and ~10 minute drive to Wolffer Estate. We experienced a few issues upon check in (had some trouble working with the electronic door lock, no toilet paper), but Eric personally called me and made it his business to resolve it. He really demonstrated being a great host and making sure that we had no issues. I would definitely stay at Eric's property again, it truly felt like a home away from home.
Home in Old Lyme
4.8 out of 5 average rating, 5 reviewsBeach Front Hawks Nest Beach (B)
Had a great time! Very comfortable and felt like home to us. Beautiful beach with fire pit. Just loved it!
Villa in Water Mill
4.96 out of 5 average rating, 28 reviewsIncredible 9+ Bedroom Watermill Home w Heated Pool
Staying at this home on Airbnb was a fantastic experience! The host was incredibly friendly and welcoming, making sure we had everything we needed for a comfortable stay. The home was beautifully decorated, clean, and spacious, with all the amenities we could ask for. The location was perfect, close to local attractions and restaurants. We enjoyed our time here and would highly recommend this to anyone looking for a memorable stay.
Home in North Fork
4.78 out of 5 average rating, 41 reviewsFarm house with vineyard views
We spent a beautiful family Christmas at Paul’s place meeting there, Christmas Day with Son, toddler grandson, and 100 pound dog. We arrived an hour early (coming from four states away with the hound) and there was a little tension about getting the code to get into the property but got in at check in time and were greeted by a beautifully kitted out pristine and cozy home at which to spend our Christmas together. The grandson loved toddling around and the dog meandered happily in the fenced in yard. Paul advised us to turn on the gas fireplace, which we did and a lovely time was had by all. There was nothing lacking in the place, bedding and beds were very comfortable, and we are definitely planning to come back for another visit someday. I can’t say enough about Southold in the entire North Fork area. It’s charming, has lots of farms and vineyards and cute boutiques and such but it’s not over built like so many other areas.
Home in Old Saybrook
5 out of 5 average rating, 41 reviewsGreat Hammcock Getaway, Nearby beaches, Hot tub
We had a lovely stay over the Christmas holiday. The space was decorated beautifully for the season, and the space was perfect for our multi-generational family group of 7 (including grandparents and young kids). Irina was responsive and helpful with any question I had. We'd love to stay here again.
Quick stats about vacation rentals in Greenport
Total rentals
170 properties
Nightly prices starting at
ﺩ.ﺇ331 before taxes and fees
Total number of reviews
9.6K reviews
Family-friendly rentals
120 properties are a good fit for families
Pet-friendly rentals
50 properties allow pets
Rentals with a pool
30 properties have a pool
Frequently Asked Questions
Are there vacation rentals with a dedicated workspace in Greenport?
Yes! Work meets play with ease at over 80 vacation rentals in Greenport featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Greenport?
Four-legged friends are welcome in Greenport. Choose from more than 50 vacation rentals for guests traveling with pets.
How much does it cost to stay in apartment rentals in Greenport?
Experience the best of Greenport with our apartment rentals, starting at about $200 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there Greenport vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 20 vacation homes with pools in Greenport, available on Airbnb. Make a splash and soak up the sun in style!
Do house rentals in Greenport have self check-in?
Absolutely! We offer over 30 house rentals with self check-in in Greenport. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Greenport have a bbq area?
Absolutely! We offer over 50 house rentals with a bbq area in Greenport. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly apartment rentals in Greenport?
Greenport has more than 10 family-friendly apartment rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for House Rentals in Greenport?
Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with self check-in, over 50 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.
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