Vacation rentals in Glen Head

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Top-rated vacation rentals in Glen Head

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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

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!

4.91 out of 5 average rating, 146 reviews
Superhost
Home in Westbury

Newly Renovated Personal Apartment in Long Island

Extremely quiet and private full apartment in Westbury, Long Island. Close to hundreds of restaurants and shops. 5 min drive to Roosevelt Field mall (biggest mall in Long Island)! 10-15 minutes from Jericho Terrace and Floral Terrace wedding venues locally! Near 6 hospitals and colleges! We live on property as well and are available for any questions. Feel free to chat as much, or as little, with us. We respect your privacy but are here to help in anyway! **No use of deck unfortunately**

4.75 out of 5 average rating, 152 reviews
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

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.

4.98 out of 5 average rating, 151 reviews
Guest favorite
A spacious living room featuring a comfortable sectional sofa adorned with decorative pillows. A large area rug anchors the seating arrangement, which includes two lounge chairs. Natural light filters through multiple windows, highlighting the neutral color palette and decorative wall art.
Home in White Plains

Spacious 3b/3b Mediterranean in White Plains

Bring the whole family to this great place with lots of room for fun, relaxation or hosting! This 3bed/3bath Mediterranean is freshly renovated with stylish touches & comfy furniture. The main floor of this multi family serves as a great spot to bring the family while visiting the area. The house boasts an oversized living room, formal dining room, large chef's kitchen, and plenty of sleeping space. With heat & AC throughout the entire 2k sf unit, this house is great for anything& everything!

4.91 out of 5 average rating, 178 reviews
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

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...

4.93 out of 5 average rating, 640 reviews
Guest favorite
Home in Huntington

Spacious Retreat w/Jacuzzis -1- Night Stay Welcome

* We are open for One Night Stays-please message for price$ Escape to this beautiful home on 3 private acres close to West Hills County Park. Enjoy the best of both worlds—serene outdoor adventures just minutes from the Walt Whitman Mall and top shopping spots. Designed for entertainment and family gatherings, this home boasts a stunning kitchen, luxurious bathrooms, and two relaxing hot tubs. Whatever your pleasure, this is the perfect getaway for nature lovers and city explorers alike!

4.9 out of 5 average rating, 48 reviews
Guest favorite
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

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.

4.86 out of 5 average rating, 314 reviews
Guest favorite
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

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 ✔ Spacious yard ✔ Charcoal Grill ✔ Crib and Pack n Play ▶ Close to locations such as: ✔ 6 mins to Tappens Beach ✔ 10 mins to Welwyn Preserve County Park ✔ 11 mins to Planting Fields Arboretum & Garvies Point Museum and Preserve ✔ 15 mins to Pryibil Beach

4.77 out of 5 average rating, 66 reviews
Top guest favorite
A bright living room showcases a light-toned leather sofa set arranged around a marble coffee table. Large windows allow natural light to fill the space, framed by soft curtains. A television is mounted on the wall, and a decorative wreath adds a seasonal touch.
Home in Port Washington

Comfortable House in North Shore, Long Island

Perfect getaway! 10 min walk to the train into NYC, Mets, MSG, US Open, Atlantic Ocean, shops, tennis & golfing. A comfortable 4 beds, 3 Baths, 4 car driveway home. Hi speed WiFi, 75", (2)65" & 55" entertainment center, eat-in kitchen, living room, family room, dining room, jacuzzi with outdoor furniture in a private cul-de-sac. This home, with modern comforts, is the perfect 'home-away-from-home' for couples or families looking for a peaceful getaway or easy access to NYC.

4.91 out of 5 average rating, 82 reviews
Superhost
Apartment in Glen Cove

Cozy Glen Cove Apt Near Ferry, Parking & NYC!

Gather the family or unwind on Long Island at this cozy Glen Cove apartment near dining, waterfront parks, and easy transit into NYC. Comfortable spaces and a prime North Shore location make it an ideal home base. This home offers: 🛏️ Three private bedrooms 🔥 Electric fireplace 🍽️ Full kitchen & dining area 📺 Smart TV & books 👶 High chair 🚗 Off-street parking Perfect for families, small groups, or travelers wanting comfort and convenience near New York City.

4.93 out of 5 average rating, 15 reviews
Top guest favorite
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

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.

4.94 out of 5 average rating, 233 reviews
Guest favorite
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 Manhasset

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

A quiet, practical home base for guests visiting Great Neck for work, medical appointments, or family matters. The suite has its own private entrance and bathroom, a king-size bed, an electric reclining sofa, smart lighting, and a refreshment nook with fridge, microwave, toaster, electric kettle, and Keurig. Close to Northwell Hospital, 20-minute walk to the LIRR, and 10 minutes by car to supermarkets, shops, the library

4.95 out of 5 average rating, 256 reviews

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