Holiday houses in Dering Harbor

4.91 out of 5 average rating, 107 reviews

Cozy Farmhouse Retreat in North Fork, NY

A 1905 farmhouse with modern touches, Arthur's Vineyard is a cozy 3-bed, 2-bath home in walking distance of Greenport village's beaches, marina, restaurants and boutiques. An open plan living area, breezy decor and a large landscaped backyard for spending relaxed summer days and nights with your family and friends, including the 4-legged ones. Walk to the train station/jitney or take a short drive to the wineries & farm stands of the North Fork. Recent updates: central heat/AC & new bathrooms.

Superhost

Condo in North Fork

4.85 out of 5 average rating, 136 reviews

Seaside Summer Escape: 2BR Waterfront Condo w/Pool

Overlooking the Long Island Sound, this oceanfront condo is the ultimate escape. Bask in the sun on a private beach or unwind on the waterfront deck with breathtaking views Minutes from the town center, you’ll find local farms, award-winning wineries, gourmet restaurants & charming shops ⚓️ Explore Greenport: A historic seaport with coastal charm & rich culture 🏖 Premium Amenities – Waterfront deck, private balcony, grills, pool, private beach & parking ⛴ Ferry Access to Shelter Island & CT

4.92 out of 5 average rating, 140 reviews

Condo in North Fork

Beachside Waterview 2Br Condo w/ Pool in Greenport

Relax in a pristine 2Br condo with ocean & pool views. Our remodeled apartment is part of high-end development nestled on LI Sound, just minutes from downtown Greenport. Sip a glass of wine while watching sunset, catch some rays on the beach or deep in the pool. 2 bedroom condo with ocean view, beach, and pool (seasonal) Comfortably sleeps 6 Private beach access year-around Pool (seasonal) Functional kitchenette 2 bathrooms, all toiletries Linens and towels are provided Smart TV AC/Heat

Guest suite in North Fork

4.91 out of 5 average rating, 316 reviews

The Greenport Suite—private entry + near the beach

Welcome to The Greenport Suite! With its separate entrance, secluded outdoor patio space and ideal location, this newly-redesigned private suite in our contemporary Village home is perfect for enjoying a North Fork getaway. We are located just a few short blocks from bay beaches, the harbor, and public transport, while the area's celebrated wineries are a short drive or bike ride away. Come see why Forbes named Greenport one of the 11 prettiest villages in the United States!

4.94 out of 5 average rating, 187 reviews

Harbor Heights

Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney. My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

5 out of 5 average rating, 13 reviews

Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV

★ "Beautiful hidden home on the water… enjoy the North Fork summer in style." Private beachfront property with 2 homes & views of Gardiner’s bay. ☞ Bikes + kayaks + paddle boards ☞ Wrap around balcony w/ seating ☞ Fully equipped + stocked kitchen ☞ Deck w/ lounging + water views ☞ Dedicated workspace + printer ☞ Master w/ king + bathroom ☞ 55” Smart TV + Xbox ☞ Indoor gas fireplace 6 mins → DT Greenport (cafes, dining, shopping) 13 mins → Orient Beach State Park ⛱

4.9 out of 5 average rating, 215 reviews

Greenport Beach house Mini Resort Spa & Catering

Nestled steps from the beach, and all that Greenport and the North Fork has to offer, this exquisitely charming 3 bedroom 2 bathroom waterfront home is absolutely delightful.. You’ll love my place because of the views, the location, the people, the ambiance, the outdoors space, and the Saltwater pool.. My place is good for couples, solo adventurers, business travelers, families (with kids), groups, and furry friends (pets).

4.96 out of 5 average rating, 105 reviews

Apartment in North Fork

Junior 1-BR in the heart of Greenport Village

Beautiful junior one bedroom in the heart of Greenport Village. Located in the historical district, our basement apartment is walking distance (2-Blocks) to downtown Greenport. Perfect for a couples weekend, girls trip, or for a small family. Our apartment includes one queen bed and a twin day bed with trundle underneath. (Sleeps 4 total) TV with streaming service and WiFi are included. W/D are available upon request.

4.92 out of 5 average rating, 305 reviews

1830 Historic garden wing - walk to it all

This historic Captain's house is located in the heart of beautiful Greenport Village. It dates back to 1830 and has been beautifully renovated preserving its historic detail. It has a huge garden with mature trees, plants and a wonderful gazebo. Once you step outside, you can walk to all the restaurants, bars, shops, the water as well as the Hampton Jitney and the LIRR. It's an ideal yet very quaint location.

Superhost

Home in Shelter Island

4.9 out of 5 average rating, 116 reviews

There's a Beach Getaway!

Welcome to our family-friendly oasis just two blocks from beautiful beaches! Our house offers an open space living area, an expansive yard, fire pits, and a basement with a playroom and workout area. Enjoy our quiet neighborhood. We provide kid-friendly toys, beach gear, bicycles, and more. Sleeps six, with additional options available for larger parties. Cleaning fees for winter stays are 0$.

Apartment in Shelter Island Heights

4.91 out of 5 average rating, 247 reviews

Squire Chase House

Wide open loft like space in the heart of the Heights walking distance to North ferry and Marie Eiffel market Many antiques including 1930s leather club chairs and a wonderful 1850 Swedish gustavian sofa in the living room many original pieces of art work Note :the bath tub in the master bedroom is for decoration only Shelter Island license B Zone

Guest suite in North Fork

4.96 out of 5 average rating, 80 reviews

Private Suite in a Greenport Historical Townhouse

Enjoy the Greenport experience at this centrally located, renovated Victorian home. Our place is a few minutes walk into town, where there is a flourishing restaurant and food scene. Lots of shops, cafes to explore too and beaches are a 15 minute walk. Take a boat tour of the harbor from nearby Preston's Dock.

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Other great holiday rentals in Dering Harbor

4.99 out of 5 average rating, 93 reviews

Greenport Village Rental

DavidRating, 5 stars10 months ago

What a perfect stay for our family of 4 (kids are 5 and 1). Michael was a very proactive host and told us everything we needed to know ahead of time. Worked with us to get us in as early as possible on check-in day. Very responsive and helpful. How was so awesome and a straight shot down to the beach. 5 minute walk into town. Can’t wait to be back soon

4.92 out of 5 average rating, 26 reviews

Stylish Getaway in Greenport

DonRating, 5 stars1 week ago

We were in town for a wedding which we found out was minutes from Danette’s place and so easy to travel to. The home was immaculate, well supplied and the pool was enjoyable. We felt at home here and is at the top of our best places to stay list. Thank you so much Danette!

4.94 out of 5 average rating, 103 reviews

Apartment in North Fork

Quaint DT Greenport Apt - 2 Mi to Shelter Island!

CarolRating, 5 stars3 weeks ago

Great accommodations for a 2 person getaway! Peaceful, quiet, beautiful location within walking distance to Greenport village. Check-in and check out was simple! The apartment is uncluttered and very clean and has everything you need for a comfortable stay!

Apartment in North Fork

4.78 out of 5 average rating, 324 reviews

Amazing Greenport Village Apartment in CENTER!

DanielleRating, 5 starstoday

This apartment is the most perfect space for a getaway. The photos dont do it justice, I was shocked at how big the space was. Right in the heart of the town I could not have asked for anything better. Lucharitos crew downstairs although not affiliated was nothing but friendly and considerate of our stay. I will be back for sure!

5 out of 5 average rating, 5 reviews

Delightful Cape House in Greenport

JeroenRating, 5 stars1 day ago

Kyra’s house is a fantastic place to stay. The location is within walking distance from the beach and town, and the place itself feels like home with an efficient layout. Patio and pool are really nice too. Would definitely recommend.

5 out of 5 average rating, 16 reviews

Cottage in North Fork

3 Min Walk to Beach| 1 mi to Town |Baby&Beach Gear

TeresitaRating, 5 starstoday

The house was clean, cozy, and the location was quiet and beautiful. The space was enough for a family of five like us. We enjoyed our stay and would try to stay again with Alia if we come back to Greenport.

Home in Shelter Island

5 out of 5 average rating, 4 reviews

Peaceful Bright Country House

Edith,CRating, 5 stars2 days ago

Adorable spot on Shelter Island—clean, quiet, and super cozy. Great location for exploring, and the perfect place to unwind. Karen the host was so accessible and very pleasant. Would definitely stay again.