Holiday houses in Woodbury

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Top-rated holiday rentals in Woodbury

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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 Cold Spring Harbor

4.93 out of 5 average rating, 113 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, 143 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

4.98 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.

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.

Apartment in Huntington

4.96 out of 5 average rating, 342 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 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 spacious bedroom features a cozy bed with decorative pillows and a light-colored blanket. Two bedside lamps illuminate wooden nightstands on either side. A small desk and chair sit against the wall, providing a work area, while angled ceilings create a unique architectural detail.

Guest suite in Huntington Station

4.9 out of 5 average rating, 132 reviews

Spacious Huntington Suite- Private and Central

The guest suite is private, spacious and will accommodate those looking to spend time in the area . The guest suite is attached to the main house by locked French doors . There are no shared spaces . You’ll love my place because it is close to public transportation (LIRR- HUNTINGTON STATION) as well as the Paramount Theater ,Huntington Village and all Huntington has to offer. Those in town for weddings and events in the Woodbury/Syosset area will find this is a great place to tip off from .

Top Guest favourite

A wooden dresser with several drawers is positioned against a wall. A round tray with decorative items sits on top, complemented by a tall vase containing dried flowers. A large mirror reflects the space, and a purple curtain drapes beside the dresser.

Apartment in Babylon

4.96 out of 5 average rating, 106 reviews

Comfy 1st Floor Convenient Abode

Our Main Street West Babylon home, located on the 1st floor, is perfect for all guests. Perfectly situated for exploring Long Island's best attractions, minutes from Belmont Lake State Park, Babylon Village & a short drive to Jones Beach, Robert Moses State Park, and the Hamptons. 2 comfortable bedrooms with plush beds & 2 bathrooms with fresh towels & essentials. Cozy living room with smart TV & Wi-Fi. Fully equipped kitchen with appliances and cookware. Backyard with a patio and parking.

Top Guest favourite

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

4.92 out of 5 average rating, 64 reviews

Spacious 2 bedroom, bathroom, eat in kitchen!

A beautiful, clean, quiet place where everyone will be comfortable!!! We welcome up to 4 people to this totally separate upstairs apartment with 2 bedrooms, eat in kitchen, living room and an outdoor deck. Close to the highways, 7 minute drive to Huntington Village, 3 minute drive to Oheka Castle. Located on the beautiful north shore of Long Island. You have free street parking. A/C, cable and internet. Please note the owners have a dog that lives downstairs with the rest of the family.

Superhost

An open living space is depicted, featuring a brown sofa adorned with decorative pillows. A modern kitchenette is visible in the background, equipped with white cabinets and appliances. Natural light streams in, complemented by neutral wall colors and a blend of wooden flooring and tiled areas.

Home in Huntington

4.82 out of 5 average rating, 50 reviews

Artist Den!

Great artist den to muse inspiration. Full kitchenette including a Keurig machine. Wonderful get away for solo traveler, couples or a family. Bedroom has a queen sized bed and comes with a full bathroom (Bath tub and shower). Fast WiFi connection. Perfect location for guests attending events at Oheka Castle, The Fox Hollow, Crest Hollow Country Club, The Royal Palm, The Mansion at Oyster Bay, Chateau @ Coindre Hall, Cold Spring Country Club and Jones Beach Reach out for availability!

Guest favourite

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, 310 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 favourite

Home in Centerport

4.95 out of 5 average rating, 174 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 favourite

A spacious living area features a blue futon sofa, a coffee table with decorative items, and a television mounted on the wall. The sleeping area accommodates a queen-size bed next to a twin bed, with natural light illuminating the room through nearby glass doors.

Guest suite in Levittown

4.94 out of 5 average rating, 222 reviews

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.

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.

Apartment in Northport

4.83 out of 5 average rating, 240 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.