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Featured Holiday Homes in Greenport

Bayfront 5 bedrooms family home. Panoramic sea view from all rooms

Bayfront 5 bedrooms family home. Panoramic sea view from all rooms

Hampton Bays NY
Stay at this holiday home in Hampton Bays. Enjoy free Wi-Fi, private pools and a fitness centre. Popular attractions Cooper's Beach and Meschutt Beach are located ...
Opens in a new windowBayfront 5 bedrooms family home. Panoramic sea view from all rooms
The SandPiper

The SandPiper

Greenport, NY
Stay at this holiday home in Greenport. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Railroad Museum of Long Island and East End Seaport ...
Opens in a new windowThe SandPiper
Charming Riverhead home with large outdoor patio & backyard  firepit

Charming Riverhead home with large outdoor patio & backyard firepit

Riverhead NY
Stay at this holiday home in Riverhead. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Splish Splash Water Park and All Star Bowling ...
Opens in a new windowCharming Riverhead home with large outdoor patio & backyard firepit
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Charming Waterfront Getaway — South Cove, Old Saybrook

Charming Waterfront Getaway — South Cove, Old Saybrook

Old Saybrook CT
Stay at this holiday home in Old Saybrook. Enjoy laundry facilities and air conditioning. Popular attractions General William Hart House and Katharine Hepburn ...
Opens in a new windowCharming Waterfront Getaway — South Cove, Old Saybrook
Hamptons Contemporary 4 beds cozy home minutes to beaches, village, US Open disc

Hamptons Contemporary 4 beds cozy home minutes to beaches, village, US Open disc

Hampton Bays NY
Stay at this holiday home in Hampton Bays. Enjoy laundry facilities and air conditioning. Popular attractions Cooper's Beach and Meschutt Beach are located ...
Opens in a new windowHamptons Contemporary 4 beds cozy home minutes to beaches, village, US Open disc
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

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

Southampton NY
Stay at this family-friendly holiday home in Southampton. Enjoy free Wi-Fi, private pools and a garden. Popular attractions Cooper's Beach and Southampton Golf ...
Opens in a new windowDelightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food

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

East Lyme CT
Stay at this family-friendly holiday home in East Lyme. Enjoy free Wi-Fi, private pools and breakfast (surcharge). Our guests praise the helpful staff in their ...
Opens in a new windowHistoric Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food
Charming Two-Story Retreat in Southampton Village walk to town, beach and train.

Charming Two-Story Retreat in Southampton Village walk to town, beach and train.

Southampton NY
The price is NZ$1,444 per night from 1 June to 2 June
NZ$1,444
1 June - 2 June
includes taxes & fees
Stay at this holiday home in Southampton. Enjoy laundry facilities, patios and air conditioning. Popular attractions Cooper's Beach and The Hamptons Beaches ...
Opens in a new windowCharming Two-Story Retreat in Southampton Village walk to town, beach and train.
Vacation Getaway - Nature Retreat with Modern Comforts

Vacation Getaway - Nature Retreat with Modern Comforts

East Hampton NY
Stay at this holiday home in East Hampton. Enjoy laundry facilities and air conditioning. Popular attractions The Hamptons Beaches and LongHouse Reserve are ...
Opens in a new windowVacation Getaway - Nature Retreat with Modern Comforts
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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.

Greenport Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Greenport vacation homes are the perfect way for you to wing it.

Holiday houses in Greenport let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Greenport in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Greenport adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Greenport with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Greenport vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Greenport Holiday Homes essential information

Accommodation
1636 Holiday Homes
Lowest Price
NZ$315
Highest Price
NZ$1,444
Popular accommodation
Bayfront 5 bedrooms family home. Panoramic sea view from all rooms, The SandPiper , Charming Riverhead home with large outdoor patio & backyard firepit, Charming Waterfront Getaway — South Cove, Old Saybrook, Hamptons Contemporary 4 beds cozy home minutes to beaches, village, US Open disc, Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping, Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food, Charming Two-Story Retreat in Southampton Village walk to town, beach and train., Vacation Getaway - Nature Retreat with Modern Comforts

Top trending hotels in Greenport

Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
The price is NZ$672 per night from 28 May to 29 May
NZ$672
28 May - 29 May
includes taxes & fees
Stay at this beach hotel in Greenport. Enjoy free breakfast, free Wi-Fi and an outdoor pool. Our guests praise the helpful staff in their reviews. Popular attractions ...
Opens in a new windowSound View Greenport
The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
209 Front St Greenport NY
The price is NZ$523 per night from 26 May to 27 May
NZ$523
26 May - 27 May
includes taxes & fees
Stay at this business-friendly hotel in Greenport. Enjoy free breakfast, free Wi-Fi and an outdoor pool. Our guests praise the helpful staff and the clean rooms ...
Opens in a new windowThe Harbor Front Inn
Zey Hotel

Zey Hotel

3.5 out of 5
439 Main Street Greenport NY
The price is NZ$315 per night from 25 May to 26 May
NZ$315
25 May - 26 May
includes taxes & fees
Stay at this boutique hotel in Greenport. Enjoy free parking, free bicycles on-site and daily housekeeping. Popular attractions Greenport Harbor Brewing Company ...
Opens in a new windowZey Hotel
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North Fork Resort

North Fork Resort

3 out of 5
690 Queen St Greenport NY
The price is NZ$499 per night from 25 May to 26 May
NZ$499
25 May - 26 May
includes taxes & fees
Stay at this cottage in Greenport. Enjoy free Wi-Fi, free parking and an outdoor pool. Popular attractions Railroad Museum of Long Island and Greenport Farmers' ...
Opens in a new windowNorth Fork Resort
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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.

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^Subject to availability and chosen travel dates.