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Greenport Holiday Rentals

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Holiday Rentals in Greenport

Beach nearby
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (181)
"Always a very nice time staying at this property. The sunset on the beach was amazing. Convenient to all area restaurants, wineries, breweries and Matchbook Distilling. "
The price is NZ$537
includes taxes & fees
16 May - 17 May
Cliffside Resort Condominiums
View from property
Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, (235)
"Everything was just as described!"
The price is NZ$326
includes taxes & fees
16 May - 17 May
Windward Shores Ocean Resort
Apartment, 1 Bedroom | Private kitchen
Driftwood Resort
3.5 star property
8.8 out of 10, Excellent, (184)
"Every room in the hotel has a little garden in the backyard which is linked with the park, it’s super natural and quiet and definitely worth to stay"
The price is NZ$344
includes taxes & fees
2 Jun - 3 Jun
Driftwood Resort
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Outdoor pool, a heated pool
Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool
9.6 out of 10, Exceptional, (48)
"We had a lovely stay at this home. It was very clean, comfortable and spacious so we could all spread out. We were glad to have a nice warm house to stay in because the weather was terrible! I also went swimming in the warm pool even though it was 60 and raining! Would highly recommend."
Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool
4 bedrooms, desk, iron/ironing board, free WiFi
North Fork Escape Near Wineries, Beaches And Hamptons
9.4 out of 10, Exceptional, (18)
"Lovely quaint home. Very clean and spacious. Perfect for a family getaway . Highly recommend."
North Fork Escape Near Wineries, Beaches And Hamptons
Outdoor dining
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖
10.0 out of 10, Exceptional, (83)
"The house was so cute and a great location. Everything was easy to deal w and Pam was very flexible with timing. Will certainly hope to stay here again!"
The price is NZ$1,607
includes taxes & fees
20 May - 21 May
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖
Outdoor pool, a heated pool
Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!
10.0 out of 10, Exceptional, (22)
"Celebrated the holidays with my grown children to be near my dad and brother. The house is lovely. We had a wonderful time. My daughter suggested we come back in the summertime to take advantage of the amenities - beautiful pool and nearby beaches. Highly recommend!!!"
Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!
Outdoor dining
Modern Farmhouse/Out Door Theater Fire Pit/ and Bocce court- WATCH VIDEO!!!
10.0 out of 10, Exceptional, (27)
"Just had a great stay at this home. Pictures are extremely accurate and this home is so comfortable, clean and well equipped. Location is excellent. Close to town, hiking, beaches, vineyards. It really has it all! Host was wonderful and responsive. Would love book another stay."
Modern Farmhouse/Out Door Theater Fire Pit/ and Bocce court- WATCH VIDEO!!!
Microwave, oven, stovetop, coffee/tea maker
Contemporary home, newly built, heated pool and hot tub, large deck and...
10.0 out of 10, Exceptional, (4)
"The property manager was incredibly helpful in providing check-in and check-out information, and was readily available to answer any questions during our stay. The house perfectly matched what we saw in the photos and was ideal for our getaway. We're already looking forward to returning in the summertime to fully enjoy the pool."
Contemporary home, newly built, heated pool and hot tub, large deck and...
Outdoor pool, a heated pool
Sagaponack Grand Estate, With Tennis Court, Newly-Furnished and 8 Bedrooms
10.0 out of 10, Exceptional, (11)
"We really enjoyed our stay in this house. Very safe and clean place to stay. Plenty of parking spaces, logs for fireplace, kitchen accessories. All china is very good quality."
Sagaponack Grand Estate, With Tennis Court, Newly-Furnished and 8 Bedrooms
Outdoor pool, a heated pool
Beautiful Family Home Nestled In The Heart Of Sagaponack
10.0 out of 10, Exceptional, (24)
"Had a wonderful time with friends in this lovely home. We had everything we needed. Excellent communication with our host. Perfect location. Thank you, Michelle 💕"
Beautiful Family Home Nestled In The Heart Of Sagaponack
Smart TV
Location and views! Located directly on Shinnecock Bay!
9.2 out of 10, Wonderful, (11)
"Since I stay for 2 days only it was fine. Check the shades , toilet paper and more towels. "
Location and views! Located directly on Shinnecock Bay!
Exterior
"Salt 'n' Lyme" - Walk to everything !
9.4 out of 10, Exceptional, (20)
"This cottage is so adorable and just a short walk to the beach and a local convenience store. This makes it easy to park the car and just walk to get coffee and such. We stayed in October so not much open this time of year, but we were in the area for a family wedding so not much time to hang out anyway. This was the first time I've rented on Vrbo, so I wasn't sure what to expect as have read a lot about obnoxious owners with tons of rules, but Brett is super-chill with only a couple of things...
"Salt 'n' Lyme" - Walk to everything !
Interior
Rustic Lakeside Cabin at White Gate Farm
10.0 out of 10, Exceptional, (90)
"Amazing place. Amazing hosts."
Rustic Lakeside Cabin at White Gate Farm
Pool
Ocean Beach Fun! 3 bedroomsDog ok with fee and signing of pet agreement!<br>
10.0 out of 10, Exceptional, (10)
"We had a big group with all different ages. Everybody enjoyed their stay. The home was clean, comfortable, and very thoughtfully decorated. The pool table, poker table and Pac-Man kept us all entertained during out time there. Hosts were friendly and responsive."
Ocean Beach Fun! 3 bedroomsDog ok with fee and signing of pet agreement!<br>
Outdoor pool
Beautiful 3 bedroom Residence in the Hamptons
Beautiful 3 bedroom Residence in the Hamptons
Smart TV, fireplace, stereo
Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
10.0 out of 10, Exceptional, (71)
"We loved this property. It’s open floor plan made it a great gathering place. Great location, clean and comfortable. Highly recommend"
Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
Beach nearby, sun-loungers, beach towels
Beach House
9.8 out of 10, Exceptional, (42)
"This was such a cute place. We visited in spring where everything is just start to bloom the yard was fenced in so great for dogs, with a cute play place for kids. The neighborhood is so quiet and peaceful. We walked several of the streets and meet a few friendly neighbors. The host was fantastic checking in to make sure we had everything we needed. The house was clean, Air with lots of windows and light. We spent time playing board games and reconnect. Definitely would come the area again and...
Beach House
Outdoor pool, a heated pool
Summer getaway
9.6 out of 10, Exceptional, (5)
"We had a great stay at the house! It was much larger than we even expected and came outfitted with everything you could need for a weekend away in July. Our host was super communicative and flexible. The pool is perfect and the location is ideal for a comprehensive weekend away in the Hamptons. We will be back- thank you again!"
Summer getaway
3 bedrooms, desk, iron/ironing board, WiFi
The Bay Cottage · Rocky Neck Park, Beach & Niantic
10.0 out of 10, Exceptional, (5)
"I booked this for a sister weekend. It was perfect for what we needed. It appears that the house was built to be a summer getaway, so it is pretty basic and no frills and comes with all the creaks and quicks of an older house. The living room is perfect for hanging out and the four chairs make it easy to rearrange to suit your needs. The kitchen is nicely stocked with everything you would need to stay with a family and the dining room is spacious enough to easily accommodate everyone staying...
The price is NZ$801
includes taxes & fees
16 May - 17 May
The Bay Cottage · Rocky Neck Park, Beach & Niantic
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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.

Other types of properties in Greenport you may be interested in

Property grounds
Greenporter Hotel
2.0 star property
9.4 out of 10, Exceptional, (49)
"Enjoyed the courtyard."
The price is NZ$269
includes taxes & fees
23 May - 24 May
Greenporter Hotel
Balcony view
The Harbor Front Inn
3.5 star property
8.8 out of 10, Excellent, (353)
"We had a wonderful stay in April 2024. The staff was very welcoming and friendly. The room was very clean- the bathroom was very up to date. This was our second stay at harborfront. We would stay agsin, for sure."
The price is NZ$484
includes taxes & fees
20 May - 21 May
The Harbor Front Inn
Lobby sitting area
Sound View Greenport
4.0 star property
8.4 out of 10, Very good, (427)
"Beautiful location. Staff was friendly and helpful. Dining was delicious. Rooms were renovated and spacious "
The price is NZ$530
includes taxes & fees
20 May - 21 May
Sound View Greenport
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Greenport holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Greenport. 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 Greenport. 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 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 holiday 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 Greenport short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Greenport?

Yes, there are holiday rentals in Greenport close to Railroad Museum of Long Island, or you can select a more secluded 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 holiday rentals that Greenport has to offer?

Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool: This holiday home rental outside of Greenport offers an outdoor pool, a fireplace and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Greenport?

With 102 Expedia holiday rentals, you're guaranteed 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 holiday rentals like in Greenport?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Greenport. Holiday rentals offer extras such as WiFi and washers and dryers to help you enjoy your stay. If you're concerned about a sanitised environment, a holiday rental can provide a sense of security away from shared hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for small groups.

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