Holiday rentals in Oyster Bay
Find and book unique accommodation on Airbnb
Quick stats about holiday rentals in Oyster Bay
Total holiday rentals
Explore 10 holiday rentals in Oyster Bay
Nightly prices starting at
Oyster Bay holiday rentals start at €70 per night before taxes and fees
Verified guest reviews
Over 1,790 verified reviews to help you choose
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
10 of Oyster Bay holiday rentals include wifi access
Popular amenities for guests
Guests love Gym, BBQ grill and Laptop-friendly workspace across Oyster Bay rentals
4.8 Average rating
Oyster Bay stays are highly rated by guests – averaging 4.8 out of 5!
Top-rated holiday rentals in Oyster Bay
Guests agree: these stays are highly rated for location, cleanliness and more.
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.
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.
Historic Huntington Village Private Retreat
65 min from NYC on LIRR to Huntington. Less than one mile from the train station and an easy walk to Huntington village in a 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!
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...
Spacious guest suite near water
Welcome to your perfect home away from home! Enjoy a spacious and newly renovated basement suite with windows and separate entrance in a private house, perfect for up to four guests. Ideal for couples, small families, or business travelers. This cozy retreat, combines privacy and comfort in a quiet neighborhood. Whether you’re here for a short trip or an extended stay, this apartment offers everything you need for a comfortable and relaxing experience. Book now and start planning your visit.
Private Huntington Suite | Near Village & Beach
Welcome to the North Suite — a private guest suite in Huntington designed for comfort, convenience, and extended stays. Enjoy self check-in, fast Wi-Fi, hotel-quality bedding, a private entrance, and a cozy space to relax after a day out. Located just minutes from Huntington Village, restaurants, shops, beaches, and major highways, this suite is ideal for couples, professionals, travel nurses, insurance stays, and longer visits. Quiet, clean, and thoughtfully designed for a comfortable stay.
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…
Spacious Retreat w/Jacuzzis -1- Night Stay Welcome
* We are open for One Night Stays-please message for price$ Escape to this beautiful home on 3 private acres close to West Hills County Park. Enjoy the best of both worlds—serene outdoor adventures just minutes from the Walt Whitman Mall and top shopping spots. Designed for entertainment and family gatherings, this home boasts a stunning kitchen, luxurious bathrooms, and two relaxing hot tubs. Whatever your pleasure, this is the perfect getaway for nature lovers and city explorers alike!
Nautical Farm House on Working Farm with Animals
Completely renovated 3 bedroom home on working farm with 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. Bedrooms have black out curtains.
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.
Bright & Private 2BR Home Near LIRR w/ parking
Private home in Hicksville with private entrance and driveway parking. Just a 10-mins walk to Hicksville LIRR, Broadway Mall and 5 minutes from Dunkin', 7-Eleven, and a local deli. Enjoy a bright living room with natural light and a mirrored accent wall, full kitchen, and separate dining room. Primary bedroom features a large built-in mirrored closet. Bathroom includes a walk-in shower, infrared heat, bluetooth speakers, and LED mirror. Enjoy access to a shared backyard.
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.
Popular amenities for Oyster Bay holiday rentals
Other great holiday rentals in Oyster Bay
Cozy Riverfront Cottage•Pool•Hot Tub•35 min NYC
Spacious Apartment Rental in Heart of Oyster Bay
The bury guest suite - 2 beautiful bedroom
Charming Oyster Bay Cottage - Walkable to Town
Primary Beachfront house
Adorable 1 bedroom beachside cottage
Locust Valley Cottage - Independent house
Locust Valley Luxury Guest House
Frequently Asked Questions
What are the best places to stay in Oyster Bay?
Stays around Oyster Bay’s historic downtown and waterfront areas are often recommended for easy access to shops, eateries, and scenic attractions. Families and groups may also find suitable accommodations near the parks and nature reserves.
What are the best things to do in Oyster Bay with kids?
Kids can take part in nature walks, explore interactive exhibits at museums, or enjoy hands-on activities at parks like Theodore Roosevelt Memorial Park. Seasonal festivals and arts programs are frequently suggested for families.
What are some of the best things to do in Oyster Bay?
Explore waterfront parks, tour historic sites like Sagamore Hill, and visit local museums to learn about Oyster Bay’s history. Outdoor activities, birdwatching, and community markets are also frequently suggested.
How is the weather in Oyster Bay?
Oyster Bay has cold winters around 29–45°F (-2–7°C), with mild, rainy springs, and warm summers reaching 72–86°F (22–30°C). Autumn brings crisp breezes and colorful foliage, so packing appropriately for the season is key.
When is the best time to visit Oyster Bay?
Late spring and summer are often recommended for milder weather, local festivals, and outdoor activities. Autumn brings colorful foliage and seasonal events, while winters are quieter and cooler around 29–45°F (-2–7°C).
What are the best places to visit in Oyster Bay?
Discover Sagamore Hill, stroll through Planting Fields Arboretum, and wander Theodore Roosevelt Memorial Park’s grounds. The local museums and waterfront areas are frequently highlighted for visitors.
What are some hiking trails in Oyster Bay?
Oyster Bay has wooded trails through nature preserves, coastal walks near the bay, and gentle paths in parks like Planting Fields Arboretum. These areas feature diverse scenery, ideal for both casual walks and birdwatching.
What are some family activities we can do in Oyster Bay?
Families frequently explore nature trails, visit local museums, or enjoy picnics in waterfront parks. Seasonal events and hands-on workshops are often suggested, creating opportunities for both fun and learning.
What are some of the best day trip ideas from Oyster Bay?
Day trips often include exploring nearby nature reserves, visiting landmarks tied to local history, or enjoying beaches and public gardens around Long Island. The area has art centers and small towns ripe for discovery.
Are there any pet friendly accommodations available in Oyster Bay?
Many accommodations in Oyster Bay welcome pets, especially around the central town or near nature areas. Parks and trails make it convenient for visitors traveling with dogs to get outdoors.
What are some local tips for visiting Oyster Bay?
Locals suggest dressing in layers, especially in spring and autumn, and trying small eateries for regional flavors. Early mornings in town and park visits during weekdays often provide a quieter experience.
What is Oyster Bay known for?
Oyster Bay is known for its maritime heritage, historic sites, and scenic waterfront. The area has close ties to natural conservation and is frequently recognized for its connection to President Theodore Roosevelt.
What are the best hidden gems to explore in Oyster Bay?
Explore tucked-away nature preserves, small art galleries, and local farm stands around Oyster Bay. Many visitors enjoy peaceful trails and community-run gardens as lesser-known spots just outside the main town.
What are the best foods to try in Oyster Bay?
Oyster Bay has classic seafood dishes, often featuring oysters, local clams, and fish from nearby waters. Visitors also frequently enjoy New York–style pizza, traditional Italian pastries, and locally roasted coffee.
What should I bring for a trip to Oyster Bay?
Pack comfortable walking shoes for exploring parks and waterfront areas, a light jacket for cool evenings, and sunscreen for summer visits. In winter, warmer outerwear is helpful, as temperatures often dip below 40°F (4°C).
What is the nightlife in Oyster Bay like?
Oyster Bay has a relaxed nightlife scene with cozy taverns, live music venues, and casual eateries around the waterfront and town center. Evening strolls and community events are frequently suggested for those seeking a laid-back local vibe.
What are the most popular events or festivals in Oyster Bay?
Oyster Bay hosts food and music festivals in late spring and autumn, farmers’ markets throughout the warmer months, and community celebrations around Labor Day weekend. Historic reenactments and arts fairs are often featured.
Are there family friendly vacation rentals in Oyster Bay?
Family friendly rentals are available in Oyster Bay, especially around downtown, the waterfront, and near parks. Many accommodations have amenities like kitchens and outdoor spaces suitable for groups.
Destinations to explore
- New York City Holiday rentals
- Philadelphia Holiday rentals
- Washington Holiday rentals
- Boston Holiday rentals
- Ocean City Holiday rentals
- Jersey City Holiday rentals
- Newark Holiday rentals
- Portland Holiday rentals
- Baltimore Holiday rentals
- Providence Holiday rentals
- Atlantic City Holiday rentals
- Newport Holiday rentals
- Times Square
- Madison Square Garden
- Central Park Zoo
- New York City Center
- Yale University
- Yankee Stadium
- Columbia University
- Jones Beach
- American Dream
- Rockefeller Center
- United Nations Headquarters
- MetLife Stadium
- Long Branch Beach
- Empire State Building
- Bryant Park
- Citi Field
- Barclays Center
- Statue of Liberty
- Grand Central Terminal
- Bear Mountain State Park
- Radio City Music Hall
- Astoria Park
- Thunder Ridge Ski Area
- Fairfield Beach