Vacation rentals in Glen Head

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Top-rated vacation rentals in Glen Head

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

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Top 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, 129 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
Barn in Bethpage
4.94 out of 5 average rating, 17 reviews

a-Bethpage#3 Mini-Barn New York Romantic Tiny Room

PLEASE READ WELL Mini-Barn 3 Small Private Room 1–2 guests only Shed converted to 1-bed room KING bed 2 windows closet hangers desk mirror smartTV, WiFi 2 towels 3 rooms SHARES 1 bath/1 small kitchen outside barn STRICT RULE:Use bathroom LESS 10 MINUTES Street parking No Pet No Visitor 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
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, 578 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, 78 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
4.68 out of 5 average rating, 44 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, 897 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.

Top guest favourite
Guesthouse in Port Washington
5 out of 5 average rating, 7 reviews

Garage Cottage House

Charming Garage Guest House - 1 Bedroom Apartment Welcome to your cozy retreat! This charming 1-bedroom apartment, located in a converted garage. The space features a living area perfect for relaxing day. The kitchen is equipped with essential appliances. The cozy bedroom offers a comfortable bed and ample storage and the convenience of a private bathroom. Near local shops and attractions, this guest house is perfect for travelers seeking a unique and comfortable stay.

The exterior of the home presents a modern design with a light-colored facade and large windows that invite natural light. A clean walkway of rectangular stones leads to the entrance, bordered by landscaped grass and gravel, set against a wooded backdrop.
Home in Oyster Bay
4.62 out of 5 average rating, 21 reviews

Tranquil Hilltop Retreat

Sitting up on a hill, secluded near the quiet woods, you will enjoy a mix between modern, luxury, and outdoorsy feels. Acres of land around with a cozy, yet modern interior, will make you feel comfortable with all the things you may possibly need for your stay. Enjoy an outdoor fire, with an outdoor kitchen or while inside in the living room watching your favorite movie. Our property offers you a peaceful secluded getaway with everything newly renovated inside and out.

The open living space encompasses a comfortable gray sofa facing a wall-mounted TV. Natural light enters through multiple windows, highlighting the warm wooden floors. A sleek table stands alongside the sofa, with an unmade bed positioned in the background, creating a versatile and inviting environment.
Apartment in Glen Head
4.58 out of 5 average rating, 65 reviews

Private estate apartment.

Relax with the whole family at this peaceful place to stay. Private apartment on tree lined estate. Full kitchen, washer and dryer. 2 Gig internet, DIsney +, HBO Max, Youtube TV, Netflix, Amazon Prime for your entertainment. Complementary really good coffee and fresh pastries in the am. Come relax and unwind. Great for families the apt sleeps 6 with one brand new King Size bed, one Queen size bed and convertible sofa full bed. Family and pet friendly.

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, 264 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*****

Top guest favourite
An open living area features a spacious layout with a light-colored sofa and a wooden dining table. Large windows offer views of the water, while recessed lighting brightens the room. A contemporary fireplace is positioned beneath a wall-mounted television, creating a cozy focal point.
Cabin in Bayville
5 out of 5 average rating, 13 reviews

Beautiful Waterfront Cottage

This is a modern new renovated water front Cottage! Private access to exclusive Bayville beach! The unit has a king size bed. A loft with Japanese style Tatami could sleep two kids. Beautiful bathroom with high tech toilet. Washer and dryer. Have fun with the whole family at this stylish place.

Popular amenities for Glen Head vacation rentals

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  4. Nassau County
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