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Vacation rentals in Oyster Bay

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Quick stats about vacation rentals in Oyster Bay

  • Total vacation rentals

    Explore 10 vacation rentals in Oyster Bay

  • Nightly prices starting at

    Oyster Bay vacation rentals start at G$16,734 GYD 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

  • Wi-Fi availability

    10 of Oyster Bay vacation rentals include wi-fi 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 vacation rentals in Oyster Bay

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite
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 Cold Spring Harbor
4.93 out of 5 average rating, 117 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 favorite
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
4.98 out of 5 average rating, 144 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.

Guest favorite
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, 144 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 favorite
A private deck overlooks a serene body of water, framed by colorful autumn foliage. A round table with multiple chairs is positioned near the water's edge, while soft sunlight creates sparkling reflections on the surface, inviting calm and relaxation.
Home in Centerport
4.86 out of 5 average rating, 36 reviews

Private Waterfront Oasis • Heated Pool + Dock

Escape to your private waterfront oasis! This serene 2-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.

Top guest favorite
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
4.97 out of 5 average rating, 346 reviews

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!

Guest favorite
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, 627 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...

Top guest favorite
Guesthouse in Rowayton
4.99 out of 5 average rating, 163 reviews

1BR full cottage, 1 min walk to private beach

Enjoy time at this lovely studio located in the heart of Rowayton, a charming New England seaside village bounded on one side by Long Island sound and the other by a tidal inlet. Based in the southwest corner of CT, we are just a 1 minute walk to 2 separate and secluded beaches as well as 2 private, well manicured parks. Great amenities in town including tennis, sailing, outdoor yoga, sunbathing, plus nice restaurants. Pedestrian and dog friendly town; you don't even need a car while here.

Top guest favorite
A cozy seating area features a wooden chair with a green cushion. Natural light floods in through the glass doors adorned with light yellow curtains, offering views of the garden outside. A patterned rug adds warmth to the space.
Cabin in Norwalk
4.95 out of 5 average rating, 116 reviews

Sunny French Cottage

This unique, sunny cottage has it's own style. Private and peaceful, completely renovated cottage with French vibes. Originally used as a painting/design studio. It is an ideal place to relax and enjoy the surrounding nature. The upstairs bedroom is loft style and has a luxurious queen size bed. It's ideal for short and long stays. It is a perfect place for cozy evenings and lazy mornings, it can also serve as a temporary workplace. High tea style, organic breakfast available (20$ per person)

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 Cold Spring Harbor
4.86 out of 5 average rating, 311 reviews

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.

Guest favorite
Home in Centerport
4.95 out of 5 average rating, 176 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 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.

Top guest favorite
Home in Greenwich
4.97 out of 5 average rating, 68 reviews

Cozy Riverfront Cottage•Pool•Hot Tub•35 min NYC

Once home to actress Misty Rowe (Hee Haw, Brady Bunch, Love Boat), this historic riverside cottage blends rustic charm with modern luxury. Cozy up by the stone fireplace, cook in the chef's kitchen, or unwind on the river-facing deck. Splash in the heated pool, soak in the year-round hot tub, gather by the gazebo, or spot wildlife along the water. Two fire pits, river views, and pure tranquility — just 5 min to downtown Greenwich and 35 min to NYC. Your riverside escape awaits.

Guest favorite
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
4.83 out of 5 average rating, 242 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.

Popular amenities for Oyster Bay vacation rentals

GymBBQ grillLaptop-friendly workspaceWifiAir conditioning

Stay near Oyster Bay's top sights

Planting Fields Arboretum State Historic Park

42 locals recommend

Theodore Roosevelt Memorial Park

10 locals recommend

Blue Water Spa

3 locals recommend

Other great vacation rentals in Oyster Bay

Top guest favorite
A spacious outdoor deck features a wooden dining table surrounded by six woven chairs, with cushions for added comfort. The serene harbor view is visible in the background, framed by lush greenery and distant houses.
Home in Centerport
5.0 out of 5 average rating, 33 reviews

Charming waterview house

Guest favorite
Guest suite in Glen Head
4.8 out of 5 average rating, 5 reviews

Long Island Nature Retreat + Peloton + Shared Pool

Guest favorite
A spacious family room is showcased, featuring a fireplace and two seating areas with elegantly upholstered sofas and armchairs. A large area rug lies on wooden flooring beneath a coffee table. Natural light filters through window treatments, illuminating decorative elements and art pieces throughout the room.
Home in Huntington
4.9 out of 5 average rating, 82 reviews

Cheerful 3 bedroom home in historical district

Guest favorite
Home in South Farmingdale
5.0 out of 5 average rating, 25 reviews

One-Bedroom Modern and Luxurious Retreat

Top guest favorite
A serene backyard scene features a sparkling pool adjacent to a stone patio. Colorful chairs surround a fire pit, framed by lush greenery and blooming flowers. The tranquil pond adds to the peaceful atmosphere, creating a relaxing outdoor space for guests.
Tiny home in Halesite
5.0 out of 5 average rating, 29 reviews

Cozy Cottage

Superhost
Guest suite in Locust Valley
4.78 out of 5 average rating, 9 reviews

Family-Friendly Retreat w/ Trampoline & Grill

Superhost
Home in Huntington
4.87 out of 5 average rating, 23 reviews

Modern Family Retreat!

Top guest favorite
The exterior view presents a charming entrance with a stone pathway leading to a white-railed staircase. Colorful flower arrangements, including roses and pink blooms, adorn the area, enhancing the inviting ambiance of the home surrounded by lush greenery.
Guest suite in Huntington
4.93 out of 5 average rating, 67 reviews

Spacious 2 bedroom, bathroom, eat in kitchen!

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

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