Vacation rentals in Oyster Bay

Home in Cold Spring Harbor

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.

4.97 out of 5 average rating, 113 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.

Apartment in Downtown Stamford

A balcony is equipped with outdoor furniture, including two chairs and a small table. The scene is enhanced by a view of the city skyline during sunset, with soft, warm lighting reflecting off the buildings. Glasses are placed on the table.

4.95 out of 5 average rating, 217 reviews

Sugar Shack Studio | Downtown Skyline Views

Location! Studio apartment located in the heart of downtown Stamford. Walk to downtown to enjoy all it has to offer, from restaurants, shopping, UCONN of Stamford and more! Centrally located and a short train ride to New York City, our apartment offers everything you need for a comfortable stay in the area. We offer free parking on the premises and the train station is a 10 minute walk. Washer and Dryer included in the building with credit card payment. This unique place has a style all its own!

4.9 out of 5 average rating, 139 reviews

A cozy studio space is presented, featuring a spacious bed with dark cushions, a small dining table and chairs, and a comfortable couch. Light walls are complemented by decorative artwork and accents. A kitchenette area is visible, along with shelving and a TV, creating a functional living space.

Cottage in Centerport

NYC/Long Island - cozy garden cottage!

Sweet garden cottage - enjoy beautiful fall colors or spring blossoms away from the City! Sunny, bright, quiet, nicely decorated, completely private. Quiet, green neighborhood, a short walk or drive from several Long Island Sound beaches*. Private entrance and parking, private bathroom with shower; kitchenette, fridge, microwave, A/C, heat. Minutes from the train station to New York City; 30 minutes drive to Robert Moses State Park/Fire Island Nat'l Seashore. *Some beaches charge a fee.

4.96 out of 5 average rating, 301 reviews

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

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!

4.93 out of 5 average rating, 552 reviews

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

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...

Apartment in Huntington Station

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.

4.91 out of 5 average rating, 199 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

4.92 out of 5 average rating, 185 reviews

A contemporary living space features a sofa with decorative pillows and a coffee table arranged on light wood flooring. Natural light filters in through large windows, illuminating the area. A small dining table with woven chairs, a television on a wall mount, and a floor lamp are included in the design.

Guest suite in Levittown

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.

4.94 out of 5 average rating, 162 reviews

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

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!

4.85 out of 5 average rating, 199 reviews

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

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.

4.95 out of 5 average rating, 175 reviews

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

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.

4.79 out of 5 average rating, 247 reviews

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

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.

Apartment in Huntington Station

A cozy studio space features a spacious king bed with floral-patterned bedding. A kitchenette and dining table are visible, along with a microwave and refrigerator. A small lamp and a teddy bear add to the homey touch. A wall clock and framed sunset photo enhance the ambiance.

4.9 out of 5 average rating, 115 reviews

Clean Cozy Studio with Private Entrance.

Comfortable Safe Studio With Private Keypad Entrance in Huntington Area. Premium CABLE TV and All Amenities described are Included. There is Keurig coffee maker with cream and sugar so you can enjoy it. Cozy studio also has a toaster, microwave, refrigerator, own bathroom and small kitchenette that you can enjoy your own meals. You have a comfy King size Bed.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Hotels

Stylish accommodations with great services and amenities

Popular amenities for Oyster Bay vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Other great vacation rentals in Oyster Bay

Tiny home in Cold Spring Harbor

A charming cottage is nestled among lush greenery, with a wooden deck leading up to it. Surrounding flowering plants and shrubs create a vibrant landscape, while a lamp post adds a welcoming touch. The natural setting enhances the tranquil atmosphere of the home.

4.94 out of 5 average rating, 78 reviews

Kokomo Cottage, Cozy Beach Town Bungalow

4.73 out of 5 average rating, 182 reviews

The studio features a spacious sleeping area with a cozy bed separated from the kitchenette and bathroom by an open layout. A well-lit kitchenette is visible, along with a small dining table and decorative items on the walls, providing a blend of functionality and comfort.

Guest suite in Stamford

Private entrance, private bathroom, quiet zone.

Apartment in East Northport

A bright interior space features a spacious bed with a blue bedspread, complemented by a desk with an office chair and a comfortable recliner. Natural light enters through two windows, enhancing the cozy atmosphere. A front door provides entry to the apartment.

4.9 out of 5 average rating, 10 reviews

Studio apt. Great neighborhood

5 out of 5 average rating, 9 reviews

The living room features a large sectional sofa adorned with a variety of decorative pillows. A glass coffee table sits in front, displaying magazines and a decorative piece. Two abstract paintings hang on the wall above, while natural light filters through sheer curtains.

Apartment in Oyster Bay

3BDRM, walk to beach, fast wifi, free parking #1

4.97 out of 5 average rating, 73 reviews

A compact kitchen area features a white dresser with several drawers, a microwave, and a black refrigerator. Above the dresser, framed wall art displays motivational phrases. A coffee maker and glassware are also arranged on the dresser, enhancing functionality in the space.

Guesthouse in Bayville

Adorable 1 bedroom beachside cottage

4.93 out of 5 average rating, 46 reviews

A spacious room features warm hardwood floors and large windows allowing natural light. A king size bed is adorned with light bedding and soft pillows. A comfortable sofa can be seen in the background, alongside a wooden coffee table and plants, fostering a relaxed atmosphere.

Apartment in Stamford

Spacious. Water Views & Access. Steps to Beach.

4.93 out of 5 average rating, 30 reviews

A modern kitchen is highlighted by a central island with seating for four. Quartz countertops and sleek cabinetry create a clean aesthetic. Pendant lights hang above, and a window allows natural light to illuminate the space. Stainless steel appliances are neatly integrated.

Home in Glen Cove

Four levels of stylish living