Holiday houses in Upper Brookville

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Top-rated holiday rentals in Upper Brookville

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

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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, 118 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.

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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, 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!

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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, 629 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...

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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

4.97 out of 5 average rating, 113 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.

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Guest favourite

Home in Huntington

5.0 out of 5 average rating, 36 reviews

Private Huntington Suite | Near Village & Beach

Welcome to the North Suite — a private guest suite in Huntington designed for comfort, convenience, and extended stays. Enjoy self check-in, fast Wi-Fi, hotel-quality bedding, a private entrance, and a cozy space to relax after a day out. Located just minutes from Huntington Village, restaurants, shops, beaches, and major highways, this suite is ideal for couples, professionals, travel nurses, insurance stays, and longer visits. Quiet, clean, and thoughtfully designed for a comfortable stay.

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Superhost

Home in Huntington

4.88 out of 5 average rating, 25 reviews

Modern Family Retreat!

Enjoy exclusive use of this private upper-level accommodation, perfect for families, business travelers, and Long Island getaways. Wonderful getaway for solo travelers, friends, couples, or families. Bedrooms feature queen-sized beds and a full bathroom with tub and shower. Fast WiFi. Also a perfect location for guests attending events at Oheka Castle, Crest Hollow Country Club, Cold Spring Country Club, and The Mansion at Oyster Bay. Permit # P233646 We are 20 minutes from Jones Beach…

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Guest favourite

Home in Centerport

4.95 out of 5 average rating, 179 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.

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Top Guest favourite

A cozy living area is showcased with a burgundy sofa adorned with patterned cushions. A wooden coffee table sits in the center, complemented by a photo of a pier on the wall. Natural light filters through a window with louvered shutters.

Apartment in Glen Cove

4.96 out of 5 average rating, 192 reviews

Comfy and very spacious apartment!

Very quiet and relaxing one bedroom apartment on cul-de-sac. This is a basement apartment, it has a flat screen TV with cable and with fully equipped kitchen, updated bathroom with extra large shower, bed linens and towels are supplied. It is located 4 miles from LIU CW post campus for those parents visiting their children. We are located 35-40 minutes from Manhattan. No public transportation near by.

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Guest favourite

The open kitchen features white cabinetry and modern appliances, complemented by a spacious countertop. A cozy living area includes a brown leather couch and an overhanging chandelier. A library ladder provides access to the small loft, while natural light filters through the windows.

Cabin in Cold Spring Harbor

4.86 out of 5 average rating, 297 reviews

Captain's Cottage on Working Farm with Animals

Charming, fully renovated cottage with cathedral ceilings and private deck. Home has a separate queen bedroom, kitchen and living room on the main floor with small stove fireplace. There is a small loft on the 2nd floor with 2 twin beds accessed by a library ladder (note: no standing headroom in loft). Private outdoor deck with seating and BBQ. Fast wi-fi, laundry access and pet friendly.

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Guest favourite

Guest suite in Glen Head

4.83 out of 5 average rating, 6 reviews

Long Island Nature Retreat + Peloton + Shared Pool

Escape to a peaceful Long Island nature retreat surrounded by farmland and quiet countryside views—perfect for guests seeking calm and comfort. 🌿 2-acre lawn + private driveway 🏊 Shared outdoor pool (Only available from May to October) 🚴 Peloton vacation rental 🪵 Charcoal BBQ grills 🐴 Horse farm next door 🍎 Youngs Farm across the street

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Top Guest favourite

Home in South Farmingdale

5.0 out of 5 average rating, 27 reviews

One-Bedroom Modern and Luxurious Retreat

One bedroom, one bathroom guest house in Farmingdale. Welcome to “The J’s”, a new construction designed for guests who appreciate modern style, warm comfort, and a touch of luxury. Perfect for getaways, business travelers, extended stays, or special occasions, The J’s offers a private, quiet retreat with all the comforts of home.

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Guest favourite

A cozy living room features a large sectional sofa adorned with decorative pillows. A glass coffee table sits on a soft area rug, while a flat-screen TV is mounted on the wall. Two windows allow natural light to fill the space, enhancing its inviting atmosphere.

Apartment in Port Chester

4.98 out of 5 average rating, 129 reviews

Sunny & Cozy Stay by Capitol Theatre/Downtown

Within walking distance of downtown Port Chester, Capitol Theatre, Metro North, and so much more; this 2 bedroom apartment with PRIVATE ENTRANCE provides a comfortable, inviting stay for those visiting the New York City/Metropolitan area. We are centrally located near the I-287, I-95, so commuting to and from the area is easy.

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