Holiday houses in Glen Head

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Top-rated holiday rentals in Glen Head

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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 Huntington
4.93 out of 5 average rating, 102 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, 128 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 spacious wooden deck features a dining table with an umbrella, surrounded by comfortable seating. Lush greenery and trimmed hedges form a serene backdrop, with vibrant plants adding color to the space. The tranquil atmosphere encourages relaxation outdoors.
Townhouse in Whitestone
4.93 out of 5 average rating, 139 reviews

Private Bath & Parking at "Suite Piece of Heaven"

Welcome to Whitestone! A quiet, upscale and safe residential neighborhood. The listing is for a private suite within the home NOT the entire house. Parking is ALWAYS available and bus stop is within blocks. - 5-7 min away by car is LGA/Citi Field/US Open - 20 min from JFK with no traffic - 44 bus takes you to the #7 train's Main St. station. From here you'll be in Grand Central in 30 min on express train. -QM2 Express bus to the city in a 1/2hr depending time of day and where you're going

Guest favourite
The kitchen and living area are designed in an open layout, featuring a white dining table with four chairs and a cozy seating arrangement. Natural light filters through a window, illuminating the neutral walls and light wood flooring. Modern appliances are present in the kitchenette, offering functionality.
Guesthouse in Valley Stream
4.93 out of 5 average rating, 28 reviews

GuesTiny Suite 30 min 》 NYC - 15 min 》JFK

Its coziness will make you feel at home the second you step in. This cute ground floor 280 sq ft Tiny Guest Suite is Fully furnished and nicely decorated - it comes with anything you can possibly imagine. It consist of 1 bedroom 1 bathroom & a kitchen/dining/living room area Rooms' sizes: Bedroom: 10ft x 7 1/2ft LR kitchen DR area: 19ft x 10ft Bath: 40" x 80" Given how close it is from everything - It is perfect for guests who plan on commuting to the city by train or move around by Uber.

Guest favourite
Barn in Bethpage
4.94 out of 5 average rating, 16 reviews

Bethpage # 3 Mini-Barn New York Romantic Tiny Room

Mini-Barn Room # 3 Small room 1–2 guests only Send guest names to host Shed converted to 1-bed house KING bed 2 windows closet,hangers,desk,mirror,smartTV,WiFi,2 towels 3 rooms share 1 bath/1 kitchen outside barn Strict Rule:10 Minutes Bathroom Use Street parking No Pets No Visitors No Wheelchair No Washer/Dryer Bring own bodywash/shampoo/conditioner $1000 penalty if smoke/vape/drugs are detected in the room Airbnb Strict/Firm Cancellation Policy You agree to FULL DISCLOSURE below if you book

Top Guest favourite
The spacious suite features hardwood flooring and modern furnishings. A king-size bed is centered against a grey wall, complemented by colorful bedding. A recliner and a sofa provide additional seating. The light refreshment area and coffee table complete the inviting setup.
Apartment in Great Neck
4.95 out of 5 average rating, 218 reviews

Eve suite, 5 mins to LIJ Hospital & train +parking

Newly renovated private suite located in the basement with private entrance and bathroom. King size bed can accommodate 2 people. Smart light fixtures and Electric sofa recliner for extra comfort. Light refreshment area with microwave, fridge, mini toaster, electric kettle and Keurig. Close to Northwell hospital and 20 mins by foot to LIRR train station. 10 minutes driving to all supermarkets, shops, library and Stepping Stone Park. Host is highly allergic to cats and dogs. No Pets Allowed!

Top Guest favourite
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, 577 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 favourite
A cozy living room features a large flat-screen TV mounted on the wall, accompanied by a sleek entertainment unit. A comfortable couch is draped with a soft blanket, and an armchair is positioned nearby. Natural light enters through two windows, brightening the neutral decor.
Guesthouse in Mamaroneck
4.96 out of 5 average rating, 77 reviews

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.

Superhost
An outdoor deck is visible, featuring a spacious arrangement of gray wicker furniture and a glass-topped coffee table. The area is surrounded by a white fence, providing a sense of privacy. Sunlight brightens the deck, highlighting the wooden flooring.
Home in Glen Head
4.74 out of 5 average rating, 43 reviews

Family Home near NY Beach | Private Workspace

Your Perfect Family Getaway Pet Friendly Awaits!! ▶ Book our spacious 3BR home & couple of mins away from the beach, complete amenities ideal for big families! Don't miss out – reserve your stay today! ✔ Private workspace ✔ Pack n Play Ready for babies! ✔ Spacious yard ✔ Charcoal Grill ▶ Close to locations such as: ✔ 6 Mns to Tappens Beach ✔ 10 Mns to Welwyn Preserve County Park ✔ 10 Mns to Planting Fields Arboretum ✔ 11 Mns to Garvies Point Museum and Preserve ✔ 13 Mns to Pryibil Beach

Top Guest favourite
A small flock of chickens is seen in a lush, green outdoor space surrounded by fencing. The chickens, displaying a variety of colors and patterns, roam on the ground among tall grass and scattered foliage. A branch is positioned in the background.
Guesthouse in Hastings-on-Hudson
4.91 out of 5 average rating, 895 reviews

★Tiny House Cottage 35 min to NYC on Hudson River★

Please read the entire listing to set expectations. Super charming, slightly quirky, never perfect private Shangri-La with backyard chickens in the artistic and quaint Rivertowns, 35 minutes from NYC along the Hudson River. The Tiny House escape is reminiscent of sleepaway camp (Rustic), yet tastefully curated with eclectic art and furnishings that can change depending on “finds.” Sleeping loft nest with 8-step ladder or pull-out sofa bed. Fenced-in yard. FREE 24/7 street parking.

Guest favourite
The living room area features two sofas, one in dark leather and the other in light upholstery, arranged around a central coffee table with a wooden surface. A lamp stands next to the seating, and natural light enters through large windows.
Apartment in Oyster Bay
4.79 out of 5 average rating, 262 reviews

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.

Guest favourite
A modern kitchen is highlighted by a central island with seating for four. Quartz countertops and sleek cabinetry create a clean aesthetic. Pendant lights hang above, and a window allows natural light to illuminate the space. Stainless steel appliances are neatly integrated.
Home in Glen Cove
4.94 out of 5 average rating, 35 reviews

Four levels of stylish living

This completed renovated house is spread over four floors of stylish and comfortable living. Spacious yet not confined. Chef kitchen is perfect for large private gathering. sleeps 10-12. PLEASE NO PARTIES ARE STRICKLY PROHIBITED. ***Effective 1/1/2026 min of 28days is required for booking*****

Popular amenities for Glen Head holiday rentals

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