Vacation rentals in Old Brookville

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!

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...

Modern Family Retreat!

Enjoy exclusive use of this private upper-level accommodation, perfect for families, business travelers, and Long Island getaways. Wonderful getaway for solo travelers, friends, couples, or families. Bedrooms feature queen-sized beds and a full bathroom with tub and shower. Fast WiFi. Also a perfect location for guests attending events at Oheka Castle, Crest Hollow Country Club, Cold Spring Country Club, and The Mansion at Oyster Bay. Permit # P233646 We are 20 minutes from Jones Beach…

Curated Suite • Soaking Tub • Walk to Whole Foods

Private one bedroom suite in Jericho featuring a Restoration Hardware Lorin live edge queen bed, a full bathroom with soaking tub, and an electric heater fireplace that warms the entire space. Enjoy a separate private entrance for comfort and ease, with a modern interior designed for relaxation. The space feels simple, comfortable, and well maintained, with quality finishes and a quiet setting. Perfect for business travel or a private, low key stay in an upscale Long Island neighborhood.

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 iconic Gold Coast! Wake up to sweeping waterfront views and, if you’re lucky, catch a glimpse of our local bald eagle family soaring overhead! Explore nearby gems like the Vanderbilt Mansion & Planetarium, Caumsett State Historic Park Preserve, Del Vino Vineyards, and the lively Paramount Theatre. Stroll through Downtown Huntington or Northport Village for boutique shopping, great restaurants.

Family Home near NY Beach | Private Workspace

Your Perfect Family Getaway Pet Friendly Awaits!! ▶ Book our spacious 3BR home & couple of mins away from the beach, complete amenities ideal for big families! Don't miss out – reserve your stay today! ✔ Private workspace ✔ Spacious yard ✔ Charcoal Grill ✔ Crib and Pack n Play ▶ Close to locations such as: ✔ 6 mins to Tappens Beach ✔ 10 mins to Welwyn Preserve County Park ✔ 11 mins to Planting Fields Arboretum & Garvies Point Museum and Preserve ✔ 15 mins to Pryibil Beach

Cozy Riverfront Cottage•Pool•Hot Tub•35 min NYC

Once home to actress Misty Rowe (Hee Haw, Brady Bunch, Love Boat), this historic riverside cottage blends rustic charm with modern luxury. Cozy up by the stone fireplace, cook in the chef's kitchen, or unwind on the river-facing deck. Splash in the heated pool, soak in the year-round hot tub, gather by the gazebo, or spot wildlife along the water. Two fire pits, river views, and pure tranquility — just 5 min to downtown Greenwich and 35 min to NYC. Your riverside escape awaits.

Spacious 1BR Stay | Near Hofstra & JFK

Enjoy a spacious, modern 1BR private suite designed for a comfortable Long Island stay. Accommodates up to 4 guests with a private entrance, comfortable bedroom, open living area, Smart TV, dining space, and convenient kitchenette. Centrally located near Hofstra University, Molloy University, UBS Arena, Roosevelt Field Mall, hospitals, and JFK Airport. Enjoy easy self check-in and the privacy of your own space within a multi-family home.

Beautiful Private Studio on LI, easy access to NYC

Close to everything yet very peaceful and relaxing, surrounded by nature. Ideally located in central Nassau with easy access to NYC, the Hamptons and famous Long Island beaches – it’s a perfect base from which to explore the best NY has to offer. For business travelers and medical residents, the apartment is close to all major airports, hospitals (NUMC, Winthrop, Northwell), universities and corporate offices throughout Nassau County.

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.

Captain's Cottage on Working Farm with Animals

Charming, fully renovated cottage with cathedral ceilings and private deck. Home has a separate queen bedroom, kitchen and living room on the main floor with small stove fireplace. There is a small loft on the 2nd floor with 2 twin beds accessed by a library ladder (note: no standing headroom in loft). Private outdoor deck with seating and BBQ. Fast wi-fi, laundry access and pet friendly.

Long Island Nature Retreat + Peloton + Shared Pool

Escape to a peaceful Long Island nature retreat surrounded by farmland and quiet countryside views—perfect for guests seeking calm and comfort. 🌿 2-acre lawn + private driveway 🏊 Shared outdoor pool (Only available from May to October) 🚴 Peloton vacation rental 🪵 Charcoal BBQ grills 🐴 Horse farm next door 🍎 Youngs Farm across the street