Holiday Homes in Long Island Sound

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Top-rated Holiday Homes in Long Island Sound

Guests agree: These holiday homes are highly rated for location, cleanliness and more.

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Top Guest favourite
A spacious dining area features a long wooden table surrounded by rattan chairs, with light streaming in from large windows. A cozy hanging chair is positioned nearby. Soft earth tones and natural materials create a calming environment, complemented by modern kitchen appliances in the background.
Holiday home in Quogue
5 out of 5 average rating, 25 reviews

The Hideout, Westhampton Beach Coastal Getaway

Welcome to the Hideout! This beautiful Hamptons getaway is the perfect escape for a staycation or vacation. The Hideout is a calm coastal design that will bring peace and serenity to anyone. This property features a gym, pool, hot tub, laundry room, and tennis court. There is also a desk with a printer, in case you have some work to do. It is about a 10 minute drive to Westhampton Main St. with food and shopping spots. It is about 8 min driving to Quogue Village beach (2.6 miles from the house)

Top Guest favourite
A spacious deck features multiple blue Adirondack chairs, all facing the tranquil waters of Long Island Sound. The horizon showcases a gentle gradient of pastel colors, signaling the transition from day to evening, while the calm water reflects the serene atmosphere.
Holiday home in Guilford
4.99 out of 5 average rating, 121 reviews

Spacious Oceanfront Getaway with Spectacular Views

Perfect vacation getaway! Awaken to the sun rising over Long Island Sound! Panoramic waterfront views from 70 ft of windows spanning NY to RI. Quiet, private, updated home, NOT a cottage: >2200 sq ft, single level 3B/3B, + bonus lower-level walk-out/office. Master bed double shower/jacuzzi overlooking the water! Multiple oceanfront decks. 100 ft granite shoreline, short stroll to nearby sand beaches. Swim, fish, read a book, or watch the sailboats go by! (Not suitable for children/pets/events.)

Top Guest favourite
Two comfortable chairs with soft cushions are positioned on a wooden deck, facing the tranquil waters of the Hudson River. A small, round table sits between them, holding two glasses. The scene captures a soft sunset glow reflected on the water, framed by distant hills.
Holiday home in Wappingers Falls
4.97 out of 5 average rating, 61 reviews

Once in a Lifetime Hudson River Views

Perfect for reunions, retreats, and celebrations. We designed Riverhouse so you can relax, recover, and get inspired. Gather in one of many common areas or chill in your own room with a view. Watch birds fly, fish jump and trains and ships go by. Chill in the hot tub, build a fire (and finally hang with your teenager), fly a kite , catch fish off a private dock. Morning coffee or sunset cocktails on the deck. Play pool, pingpong, or piano into the night. Drum circle and a dance party? YES!

Top Guest favourite
An elegantly set dining table displays black plates, clear glassware, and cloth napkins. A lit candle adds a soft glow, while a modern kitchen is visible in the background, featuring stainless steel appliances and a cozy living area with seating.
Holiday home in Warren
4.98 out of 5 average rating, 193 reviews

Private new house on 10 acres of pristine nature

Brand new home! Bring friends and family to this private and stylish place. House provides everything you need for a comfortable and peaceful stay. Fully equipped kitchen, inviting living spaces, large front and back yards with many exploring trails and a pond a few steps away from the house. Close to many 5 star restaurants, wineries, galleries and shops. Hiking, swimming, boating, skiing just to mention a few outdoor activities Close by: Kent School Mohawk Ski Area Lake Waramug High Watch

Guest favourite
A cozy bedroom is furnished with a spacious bed, featuring white linens with subtle floral patterns. A small table and a chair are positioned nearby, while natural light enters through a window above the bed. An air conditioning unit is mounted above the closet.
Holiday home in Elmont
4.81 out of 5 average rating, 117 reviews

Lovely 2-Bedroom Elmont Apartment (Lower Level)

Enjoy this centrally-located lovely full 2-bedroom private lower level apartment. With 2 Queen sized beds, this space can host up to 4 people comfortably. Ideal for travelers or families visiting NY. Located in a quiet neighborhood. In the center of many shops, restaurants, highways. This apartment is located 7 minutes away from the USB Arena, 10-15 minutes away from JFK airport, and in close proximity to Roosevelt Field Mall and Green Acres Mall. The next adventure is never too far away!

Top Guest favourite
Holiday home in Pine Hill
4.99 out of 5 average rating, 148 reviews

The Perfect Catskills Escape for Families and Groups

Pine Hill House is a renovated 1870s boarding house with loads of old charm mixed in with new luxuries. Take a left from the house to find miles of hiking trails. Take a right and walk to town with its vibrant restaurant scene and a lively community center. Belleayre Beach and Belleayre ski area are both a 5-minute drive away, as are some of the Catskills' hottest restaurants, spas, and cider houses. Don't want to leave? Relax around the woodburning stove and soak in the clawfoot tub.

Guest favourite
A sleek, modern outdoor area features a table lightly dusted with snow, surrounded by illuminated string lights. The glass walls provide views of a snow-covered landscape with trees and a flowing river, creating a serene winter atmosphere.
Holiday home in Shandaken
4.98 out of 5 average rating, 212 reviews

Unique BellEayre River retreat

#2024-STR-AO-85 As seen in Chronogram magazine Chronogram/docs/chronogram-april-2023 High ceilings, Rough cut beams, All new HVAC and Hearthstone soapstone wood burning stove. Take it easy at this tranquil getaway while you see and hear only the water flow with wrap around 4 season river right off deck. Close to scenic hiking, skiing, river tubing, and great restaurants along "Rapid Water"- The Algonquin Nation word for "Shandaken". Dogs welcome (Up to 2), sorry no cats.

Top Guest favourite
An open living space features a comfortable sofa and armchair, set on a patterned area rug. A modern kitchen island with bar stools provides seating, while stainless-steel appliances complement the light cabinetry. Natural light fills the room through two windows.
Holiday home in Highlands
4.96 out of 5 average rating, 119 reviews

2BR Oceanview Shore House, walk to beach/nightlife

** Beautiful newly renovated 2 bedroom that is walking distance from the NYC ferry, numerous bars and restaurants with live music, and steps away from the beach. Come explore the Highlands, where small town charm meets the Jersey shore. Everything is walking distance in this 1 square mile town. Enjoy waterfront restaurants , night life, tiki bars, fishing, kayaking, biking on the Henry Hudson Trail, hiking in Hartshorne Woods Park, and of course Sandy Hook Beaches.

Top Guest favourite
A scenic view captures a shoreline with sandy beaches and a calm sea. Lighthouse structures are visible in the distance against a backdrop of fluffy clouds. A person walks along the water's edge, while boats can be seen dotting the water.
Holiday home in New London
4.99 out of 5 average rating, 212 reviews

Modern & Cozy Beach House - Walk to Ocean Beach

Welcome to our modern and cozy vacation apartment in a quiet community just a 5 minute walk to Ocean Beach! ~Special features~ • Dog-friendly! Fully fenced backyard • Central Air Conditioning • New in-unit washer/dryer • 2 BR w/Queen Tuft&Needle mattresses • Futon and couch both fold into add’l beds • Gourmet kitchen; fully equipped & open concept island seating • Coffee bar w/complimentary K-cups • Patio seating area w/firepit & charcoal grill

Top Guest favourite
An inviting living area is presented, featuring a white brick fireplace as a focal point. Comfortable seating includes light-colored sofas adorned with varying throw pillows. Large windows allow natural light to fill the space, and double doors lead to the outdoor area.
Holiday home in Montauk
4.99 out of 5 average rating, 109 reviews

2 BR apartment near ocean in Hither Hills

Relax and enjoy a peaceful stay that is a 3 block walk to one of the most beautiful ocean beaches in the Hampton's! This apartment is located in a beautiful, wooded, quiet neighborhood. Town is 1.5 miles away. This apartment has an open concept living space with a fully equipped kitchen. There are 2 cozy bedrooms and one bath with a walk in shower. We prefer families and mature adults. We supply beach towels, chairs, umbrella and beach wagon.

Guest favourite
An open kitchen and dining area feature natural wood floors and high ceilings. The kitchen is equipped with modern appliances and a large island. Windows allow ample natural light, illuminating the dining table and additional seating areas. Exposed wooden beams add a rustic touch.
Holiday home in Salt Point
4.92 out of 5 average rating, 79 reviews

Riverfront rustic farmhouse near Rhinebeck

This historic Clinton Hollow house was built by Isaac Fraleigh in the late 1700's and overlooks the waterfalls of Wappingers Creek. The house has the architectural details of an antique colonial and the open, spacious feel of a modern contemporary. The great room with its big fireplace has different vibes and seating areas and is just perfect for family and friends gathering. The Petanque field in the garden add a fun convivial activity.

Superhost
An open living area features a spacious couch and coffee table, complemented by a TV. Bright natural light pours through a skylight and large windows, creating a welcoming space. An adjacent dining area includes a table and chairs, with decorative plants adding a touch of greenery.
Holiday home in Asbury Park
4.88 out of 5 average rating, 113 reviews

1 Bedroom Apt with Private Roof Deck Near Beach

This newly renovated 1 bedroom apartment has everything needed for your beach getaway. The property is located a 5 minute walk from the boardwalk and beach and includes 2 adult beach badges with beach blanket and 2 beach towels. Downtown with plenty of restaurants and bars is only about a 10 minute walk. Feel like staying in? Our private roof deck is the perfect place to relax for a quiet dinner in.

Popular amenities for Long Island Sound holiday homes

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