Holiday houses in Oyster Bay

4.79 out of 5 average rating, 121 reviews

Home in Westbury

Newly Renovated Personal Apartment in Long Island

Extremely quiet and private full apartment in Westbury, Long Island. Close to hundreds of restaurants and shops. 5 min drive to Roosevelt Field mall (biggest mall in Long Island)! 10-15 minutes from Jericho Terrace and Floral Terrace wedding venues locally! Near 6 hospitals and colleges! We live on property as well and are available for any questions. Feel free to chat as much, or as little, with us. We respect your privacy but are here to help in anyway! **No use of deck unfortunately**

4.9 out of 5 average rating, 112 reviews

Home in Rye

1956 House of the Year Award. Easy commute to NYC.

Architectural masterpiece, designed by famous architect Ulrich Franzen. House of the year awarded in 1956 by Architectural Record, featured in LIFE and House and Garden magazines. Taste the unique experience of modernist living, surrounded by nature yet walking distance to the beautiful town of Rye, the beach, natural parks and 45m by train to NYC. The house is filled with light,all the rooms have forest views,you feel inmersed in nature while enjoying the magical experience of modernist living!

Home in Cold Spring Harbor

4.99 out of 5 average rating, 101 reviews

Captain’s Cottage Water Views -3 Bdrm

Enjoy this this light and airy home with spectacular sunset & water views. 5 minute drive to private beach. Oversized deck and 2 porches all with water views. Located in idyllic, historic Cold Spring Harbor. Explore the green belt with access from rear yard. Walk to shopping, restaurants, live music, fishing or picnic in the local park. Sip a glass wine & enjoy the beautiful sunsets from the expansive deck with firepit. Upstairs loft bedroom has a fireplace & private deck w/ water view.

4.96 out of 5 average rating, 291 reviews

Apartment in Huntington

Historic Huntington Village Private Retreat

50 min from NYC on LIRR to Huntington. Less than one mile from the train station and an easy walk to Huntington village in an historic, vibrant, relaxed and unique neighborhood. Plenty to do in the area with many parks and beaches and a great place to enjoy nature. It is a short walk (a half mile) to Huntington village where there are many great restaurants, bars, and shops, plus the Paramount Theater. This stylish comfortable place is clean, cozy and quiet. Sorry, no pets allowed, dander-free!

4.85 out of 5 average rating, 294 reviews

Home in Huntington

Nautical Farm House on Working Farm with Animals

Completely renovated nautically inspired 3 bedroom home on working farm, complete with wood burning fire place and piano. Lux kitchen features stainless steel appliances, Sub-zero refrigerator, and marble counters Private, fenced backyard with BBQ. Farm has goats, pigs, chickens, bee hives, ducks, and on-site cafe and bakery. Close to Huntington village, bike trails nature walks, restaurants, parks, and the beach. Fast wi-fi, laundry access and pet friendly. New beds and baby grand piano.

4.92 out of 5 average rating, 532 reviews

Guest suite in Bayville

Romantic, Cozy and Private, 1 Block from Beach

Relax in your private romantic retreat with Canopy Queen Bed & Beautiful modern bathroom, 1 Block from beach, Second floor studio with small fridge, microwave, coffee maker, induction cook top, SmartTV... Just 7 min from the Long Island Railroad, Oyster Bay stop. Near to restaurants, shops, tennis courts. You can go biking, swimming, fishing, play golf, rent kayaks, motor boats, paddle boards. Visit Arboretums, Historic sites, Parks, walk along the water, go to the nearby movies and more...

Home in Huntington Station

4.92 out of 5 average rating, 226 reviews

THE OASIS @ LONG ISLAND

A true home away from home that sits right in the heart of Huntington NY with shops, cafes and entertainment all within 10 minutes in either direction and Manhattan just a 50 minute drive away. The house is immaculately presented and offers guests all the comforts of home including a stocked fridge filled with complimentary drinks and a fully stocked coffee bar. Watch the world go by out of the two large bay windows or watch the sunset from your own private balcony. Come and enjoy the Oasis.

4.99 out of 5 average rating, 139 reviews

Home in Commack

GOOD VIBEZ HOUSE! Golf-Heated Pool-HotTub-GameRm!

STAY. SOMEWHERE. DIFFERENT. This isn’t just a stay—it’s an experience. Welcome to THE GOOD VIBEZ HOUSE! Your private escape in the heart of Long Island. This smart home is located in a safe, quiet neighborhood, this unique retreat is the perfect getaway from the hustle and bustle of the city or everyday life. From the moment you arrive, it feels like vacation. As Superhosts, we go beyond hosting—with warm hospitality, thoughtful touches, and a five-star atmosphere you won’t forget.

4.96 out of 5 average rating, 140 reviews

Cottage in Weston

The River Loft

Escape to The River Loft, a private riverfront retreat in Weston, CT. Built in 2015 by a visionary local architect, The River Loft open-air design seamlessly integrates the outdoors with the interior space. As you step inside this 750 sf small home, you'll be instantly captivated by the layout that makes it feel spacious. Sitting on over 2 acres of forested land with private river access. Book now for an unforgettable experience. For more images & videos visit insta @the.riverloft

Apartment in Huntington Station

4.92 out of 5 average rating, 189 reviews

Lovely brand new apt 2 min away from train station

Have a fun getaway at this stylish beautiful place. In a brand new home, super fast wifi for remote work for business travelers or family. Walking distance from train station and 5 minutes away from Huntington Historic Village or take a 45 min train ride to NYC. Enjoy all the local restaurants, shops, bars and Paramount theater. Do you want to take a flight around NYC on a private plane? Ask host for more details. Central AC/Heat 1GB wifi speed

4.94 out of 5 average rating, 153 reviews

Home in Centerport

The Harbor House: Beachfront Home 1 hour from NYC

FEATURED #1 on Refinery29's "11 Best Beach Houses Near NYC"! Welcome to Long Island's Gold Coast! Enjoy stunning beachfront views from this charming home. You may spot the bald eagle family that lives around the corner! Local spots to visit include the Vanderbilt Mansion and Planetarium, Caumsett State Park Preserve, Del Vino Vineyards, Paramount Theatre, Downtown Huntington, Northport Main Street shops and restaurants, and more!

4.95 out of 5 average rating, 171 reviews

Apartment in Glen Cove

Comfy and very spacious apartment!

Very quiet and relaxing one bedroom apartment on cul-de-sac. This is a basement apartment, it has a flat screen TV with cable and with fully equipped kitchen, updated bathroom with extra large shower, bed linens and towels are supplied. It is located 4 miles from LIU CW post campus for those parents visiting their children. We are located 35-40 minutes from Manhattan. No public transportation near by.

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Other great holiday rentals in Oyster Bay

Private room in Huntington Station

4.93 out of 5 average rating, 112 reviews

Huntington Station: A room for professionals.

TashariRating, 5 stars1 month ago

Very nice couple. Very responsive. Very beautiful home. It is shared space with other individuals. Lovely place everything updated and nice.

5 out of 5 average rating, 9 reviews

Cottage in Bayville

Charming beach cottage, newly renovated.

MariaRating, 5 stars9 months ago

Beautiful cottage in Bayville. We enjoyed our stay and felt right at home. Clayton’s house is within walking distance to beach, playground, and coffee shop. Clayton’s neighbors were very friendly and would greet us every morning. We felt very welcomed and plan to visit again!

Private room in Glen Cove

4.9 out of 5 average rating, 108 reviews

Terrific Suite in Long Island NY

EmmyRating, 5 stars1 month ago

Lilly was very kind and hospitable. The place is an easy distance to the LIRR pickup spot onto the city. Definitely would recommend!

Private room in Huntington Station

4.99 out of 5 average rating, 101 reviews

Quiet private mother-in-law suite

LuciusRating, 5 stars3 weeks ago

Denise has a beautiful, safe, and clean guest suite. The neighborhood is also safe and walkable from the LIRR train stop at (Huntington)—about 1.5 miles away—with sidewalks covering about 99% of the route. This makes it great for exploring without a car! Denise is such a sweet, smart, and funny woman. I would definitely stay here again whenever I'm back in NYC ❤️

Apartment in Hicksville

5 out of 5 average rating, 4 reviews

Nice Updated Apartment In Hicksville NY

SaraRating, 5 stars1 week ago

We had a wonderful stay! We were able to check in early which was great because we had a very early flight so we needed a nap!!