Vacation rentals in Oyster Bay

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Top-rated vacation rentals in Oyster Bay

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Guest favorite

A modernist house is surrounded by vibrant autumn foliage, showcasing a blend of red, orange, and green leaves. The structure features large glass windows and a roof that floats above the walls, offering scenic views of the lush forest.

Home in Rye

4.91 out of 5 average rating, 126 reviews

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!

Guest favorite

A serene waterfront scene captures several boats anchored in calm waters, with a backdrop of trees showcasing autumn foliage. Vintage and modern homes are visible along the shore, creating a picturesque town ambiance along the shoreline.

Home in Cold Spring Harbor

4.97 out of 5 average rating, 116 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.

Top guest favorite

A studio space features a spacious bed dressed in neutral linens, complemented by contemporary furniture. A kitchenette with sleek dark cabinets is visible, along with a dining table and chairs. Soft lighting creates a warm ambiance, with modern decor enhancing the cozy layout.

Apartment in Huntington

4.96 out of 5 average rating, 309 reviews

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!

Guest favorite

The spacious suite features hardwood flooring and modern furnishings. A king-size bed is centered against a grey wall, complemented by colorful bedding. A recliner and a sofa provide additional seating. The light refreshment area and coffee table complete the inviting setup.

Apartment in Great Neck

4.95 out of 5 average rating, 211 reviews

Eve suite, 5 mins to LIJ Hospital & train +parking

Newly renovated private suite located in the basement with private entrance and bathroom. King size bed can accommodate 2 people. Smart light fixtures and Electric sofa recliner for extra comfort. Light refreshment area with microwave, fridge, mini toaster, electric kettle and Keurig. Close to Northwell hospital and 20 mins by foot to LIRR train station. 10 minutes driving to all supermarkets, shops, library and Stepping Stone Park. Host is highly allergic to cats and dogs. No Pets Allowed!

Superhost

A light-filled living area features a comfortable sofa adorned with nautical-themed pillows. A wooden coffee table rests on a woven rug, while a stylish floor lamp and wooden chair enhance the space. The ceiling showcases exposed beams, adding character to the room.

Home in Huntington

4.85 out of 5 average rating, 301 reviews

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.

Top guest favorite

A bright and airy studio space features a canopy-covered bed draped with sheer fabric. An ornate mirror and a small table with decorative items enhance the room's charm. Natural light fills the area through large windows, complemented by a cozy seating option.

Guest suite in Bayville

4.93 out of 5 average rating, 569 reviews

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...

Guest favorite

A cozy seating area features two light-colored armchairs with wooden frames. A potted plant adds a touch of greenery, and a small plate of snacks rests on a side table. Soft light emanates from a stylish floor lamp, enhancing the inviting atmosphere.

Apartment in Huntington Station

4.92 out of 5 average rating, 205 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

Guest favorite

An inviting waterfront deck is displayed, featuring two lounge chairs with striped fabric and a small table. A fire pit sits nearby, surrounded by a clear view of the bay, where sailboats are gently anchored. Lush greenery lines the horizon, enhancing the serene atmosphere.

Home in Centerport

4.94 out of 5 average rating, 163 reviews

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!

Superhost

A wooden dock extends into the water, lined with boats gently bobbing on the surface. Lush green hills rise in the background, while a clear blue sky with scattered clouds frames the scene. People are gathered along the dock, enjoying the views.

Apartment in Northport

4.85 out of 5 average rating, 205 reviews

Harbor Studio - Across from historic Northport doc

Across the street from historic Northport dock and the beautiful town park, this downtown studio is walking distance to everything. Drive or boat in to town and have a lovely convenient place to stay close to everything. Dining, shopping, the park, and the Famous Engleman theater. The studio has a private entrance, full kitchen, and bath with shower and tub. Enjoy a night, weekend, or whole week in historic Northport Village.

Top guest favorite

A cozy living area is showcased with a burgundy sofa adorned with patterned cushions. A wooden coffee table sits in the center, complemented by a photo of a pier on the wall. Natural light filters through a window with louvered shutters.

Apartment in Glen Cove

4.96 out of 5 average rating, 178 reviews

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.

Superhost

The living room area features two sofas, one in dark leather and the other in light upholstery, arranged around a central coffee table with a wooden surface. A lamp stands next to the seating, and natural light enters through large windows.

Apartment in Oyster Bay

4.79 out of 5 average rating, 254 reviews

Spacious Apartment Rental in Heart of Oyster Bay

Full 2nd-floor apartment rental in a legal 2-family home in the heart of Oyster Bay. 3 bedrooms, large living room & nice fully equipped kitchen. Wifi & cable A brief walk down into town. Walk to LIRR to NYC and JFK air-train. Short drive to Sagamore Hill, Planting Fields, Cold Spring Harbor & Huntington Village Good proximity to NYC or points east. Having a vehicle is highly recommended.

Guest favorite

A modern studio space features a large white bed with a tufted headboard, complemented by dark cabinetry and wood flooring. A comfortable seating area and a stylish coffee table are visible, alongside shelves displaying books and decorative items. Natural light enters through large windows.

Guest suite in Huntington Station

4.97 out of 5 average rating, 348 reviews

SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN

Welcome to the perfect private space to unwind. This modern studio is fully equipped with all of the conveniences you’ll need for a great stay - plus little touches that make it feel special. The Secret Hideaway is a comfortable retreat where you can recharge your batteries and plan your exciting Long Island adventures.