Holiday rentals in Oyster Bay

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Top-rated holiday rentals in Oyster Bay

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Guest favourite
An open-plan studio space features a spacious bed covered with a striped blanket, laundry appliances prominently located, and a modern kitchen equipped with high-end appliances. Bright lighting and decorative wall art add to the contemporary feel.
Guest suite in Huntington
4.93 out of 5 average rating, 98 reviews

Ultra-Modern Studio | Near Hospital & NYCIM | WiFi

Located within a friendly, leafy neighborhood is this contemporary-styled studio with everything you could need for a relaxing stay just minutes from all the action. The studio features bright, open-plan living with a fully equipped kitchen, an inviting bedroom space with a comfortable beanbag chair and Smart TV, a modern bathroom and a dedicated workspace with free WiFi. Stay only minutes to hospitals, shopping malls, restaurants and Huntington Village with its chic bars and boutique shops.

Guest favourite
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, 127 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 favourite
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, 118 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 favourite
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.
Flat in Huntington
4.96 out of 5 average rating, 310 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!

Top guest favourite
A peaceful sunset reflects on the calm waters of the pond, surrounded by lush trees and a gently sloping landscape. The sky displays a blend of warm colors, creating a serene and tranquil atmosphere that enhances the natural beauty of the waterfront setting.
Home in Centerport
5 out of 5 average rating, 24 reviews

Waterfront Home, Heated Pool, 1 Hour from NYC

Escape to your private waterfront oasis! This serene 3-bedroom, 2.5-bath waterfront retreat offers a heated pool (May-Sept), private dock, kayaks, fire pit, pickleball and BBQ lounge. Set 200 feet off the road on a private driveway, it’s perfect for families or quiet getaways. Just 8 minutes west to Huntington’s vibrant shops and restaurants, 6 minutes east to charming Northport Village, and 1 hour by train to NYC. Relax, recharge, and create lasting memories in this peaceful Long Island haven.

Guest favourite
Barn in Bethpage
5 out of 5 average rating, 12 reviews

Bethpage New York Small Romantic Mini-Barn Room #3

Mini-Barn Room # 3 Small room 1–2 guests only Send guest names to host Shed converted to 1-bed house KING bed 2 windows closet,hangers,desk,mirror,smartTV,WiFi,2 towels 3 rooms share 1 bath/1 kitchen outside barn Strict Rule:10 Minutes Bathroom Use Street parking No Pets No Visitors No Wheelchair No Washer/Dryer Bring own bodywash/shampoo/conditioner $1000 penalty if smoke/vape/drugs are detected in the room Airbnb Strict/Firm Cancellation Policy You agree to FULL DISCLOSURE below if you book

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 favourite
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, 572 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 favourite
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.
Flat in Oyster Bay
5 out of 5 average rating, 10 reviews

3BR APT #1 Central location Free parking Fast WiFi

3 bdrm apt. Everything you need at your fingertips. We have made every effort to make this apartment feel like a cozy and comfort retreat. Smart TVs with streaming apps, high speed wifi, separate entrance, large backyard with BBQ. washer&dryer on site. Free parking. Walk to the Beach, Marina, enjoy kayaking paddle board, sailing, fishing. Walk to nearby downtown area restaurants; 2 Springs, Wild Honey. Near parks, museums, shops., 45 mins to the Hamptons, Montauk, NYC by car or LIRR.

Guest favourite
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
4.95 out of 5 average rating, 166 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.
Flat in Northport
4.85 out of 5 average rating, 207 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 favourite
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.
Flat in Glen Cove
4.96 out of 5 average rating, 179 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.

Popular amenities for Oyster Bay holiday rentals

Quick stats about holiday rentals in Oyster Bay

  • Total rentals

    10 properties

  • Nightly prices starting at

    ₹5,279 before taxes and fees

  • Total number of reviews

    1.7K reviews

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    10 properties include access to wifi

  • Popular amenities

    Gym, BBQ grill and Laptop-friendly workspace

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