
Holiday rentals in Oyster Bay
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Top-rated holiday rentals in Oyster Bay
Guests agree: these stays are highly rated for location, cleanliness and more.

Fire Island Pines: Studio Cabin
Studio cabin (approx. 13.5 x 15 ft.) Functional, basic, rustic, atmospheric—It's just a little cabin in the woods. The shack can accommodate only 2 people max. Queen bed (sheets, blankets) Bathroom (shower/towels) Kitchenette (fridge, microwave, sink, dishwasher, dishes, cutlery, glasses) A/C (window unit) Fan Basic tv Internet Beach chairs/umbrellas, Outside shower The Pines is primarily a gay community, but welcoming to all. We love our wild deer and squirrels but no pets in the cabin

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 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!

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...

Charming House Near Village and Park in Huntington
This charming restored historic house in Huntington Village offers 3 bedrooms with 2 queen, 1 full sized beds, a fully equipped kitchen, comfortable living areas, including a home office. Fresh linens, towels, and toiletries are provided. There are bathrooms both upstairs and downstairs, and guests can enjoy a beautifully landscaped grounds including a private backyard, stone fireplace, multiple patios, outdoor dining table and chairs, loungers, lawn games, golf green with clubs and balls .

Modern Family Retreat!
Bring the whole family to this great place with lots of room to unwind, relax and enjoy Long Island! Wonderful get away for solo traveler, friends, couples or a family. Bedrooms have a queen sized bed in each room and comes with a full bathroom (Bath tub and shower). Fast WiFi connection. Also perfect location for guests attending events at Oheka Castle, Crest Hollow Country Club, Cold Spring Country Club, The Mansion at Oyster Bay Permit # P233646 We are 20 minutes drive to Jones Beach…

Cool pad, Private Rms, Walk to village, Wtr view
Beautiful pad on a tranquil street and walkable neighborhood. 5-10 minute walk to the village and 2-minute walk to the cliffs overlooking the bay and sound. Water view from one bedroom, great outdoor yard - very private. Updated amenities, marble bathroom, cozy indoor living area and very comfortable beds. The rental space is private and is the entire first floor of the home. The home is a two-story duplex with a shared entrance and private locking doors to each space. Wonderful location.

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.

Cozy Glen Cove Apt Near Ferry, Parking & NYC!
Gather the family or unwind on Long Island at this cozy Glen Cove apartment near dining, waterfront parks, and easy transit into NYC. Comfortable spaces and a prime North Shore location make it an ideal home base. This home offers: 🛏️ Three private bedrooms 🔥 Electric fireplace 🍽️ Full kitchen & dining area 🎮 Books, board games & Smart TV 👶 High chair 🚗 Off street parking Perfect for families, small groups, or travelers wanting comfort and convenience near New York City.

Beautiful guesthouse - Larchmont
Newly furnished 2nd floor detached studio with private entrance. One large bedroom with queen-size bed, full bath with spacious shower, kitchenette, and armoire. Lots of light and beautiful views overlooking luscious landscaping and the surrounding quiet Rouken Glen neighborhood. Studio sits over garage. Access to spare washer/dryer in our basement is also available. 4 min drive to Larchmont station (35 min train to Grand Central).

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.

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 retreat with fenced in yard—centrally located

Northport Harbor Boathouse!

Locust Valley Luxury Guest House

Tranquil Hilltop Retreat

Huntington Home w/ Pond View - 1 block to beach

Downtown Oyster Bay 3BR-Walk to Beach& Restaurants

Locust Valley Cottage - Independent house

Adorable 1 bedroom beachside cottage
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 £44 per night before taxes and fees

Verified guest reviews
Over 1,760 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!
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- Times Square
- Madison Square Garden
- New York City Center
- New York University
- Central Park Zoo
- Columbia University
- MetLife Stadium
- Yale University
- Yankee Stadium
- United Nations Headquarters
- Jones Beach
- Rockefeller Center
- Empire State Building
- Citi Field
- Grand Central Terminal
- Bryant Park
- Statue of Liberty
- Radio City Music Hall
- USTA Billie Jean King National Tennis Center
- Thunder Ridge Ski Area
- Astoria Park
- Long Branch Beach
- The Metropolitan Museum of Art
- Fairfield Beach





