
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.

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!

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
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!

A Bethpage#3 New York Private Room Mini-Barn
READ CAREFULLY YOU CANNOT CANCEL if issues are CORRECTABLE Other GUESTS share this place 1–2 guests Small private room Shed House Share 1 bath/1 kitchen with 2 OTHER ROOMS STRICT: Use the Shared Bathroom in LESS THAN 10 minutes KING bed 2 windows Closet Desk Mirror Smart TV WiFi 2 towels Street parking No pets NO VISITORS No washer/dryer Bring your own body soap/shampoo/conditioner $1000 penalty for smoke/vape/drugs in the room Strict/Firm Cancellation Policy You agree to FULL DISCLOSURE below

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.

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...

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…

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

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.

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.

Adorable 1 bedroom beachside cottage
1 bedroom peaceful guest cottage on the Bayville beach with pullout couch and sleeping for 3. The small pull out located in the main room, good for two children or 1 adult. Cottage is located behind our main house, completly renovated one year ago. Contains a microwave, coffee pot and refrigerator/freezer. Beach chairs and towels will be provided. Walk to local restaurants and market.

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.
Popular amenities for Oyster Bay holiday rentals
Other great holiday rentals in Oyster Bay

2 Beds with private Main Entrance

Private Cozy Bedroom on the 2nd Floor

(#2) Small Private Bedroom in Westbury

Bright Comfortable Room 2-A

Quaint Room for Peace and Quiet

Quiet private mother-in-law suite

Cozy Private BR in Guest Suite - Close to All

Private room in a house
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 £45 per night before taxes and fees

Verified guest reviews
Over 1,660 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
- Rockefeller Center
- Madison Square Garden
- Bryant Park
- New York Public Library - Bloomingdale Library
- Grand Central Terminal
- Columbia University
- Central Park Zoo
- Yale University
- MetLife Stadium
- Jones Beach
- Yankee Stadium
- United Nations Headquarters
- Citi Field
- Fairfield Beach
- Empire State Building
- Statue of Liberty
- Radio City Music Hall
- Canarsie Beach
- USTA Billie Jean King National Tennis Center
- Rye Beach
- The Metropolitan Museum of Art
- Gilgo Beach
- Astoria Park




