Holiday Homes in Fairfield

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Top-rated Holiday Homes in Fairfield

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

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Guest favourite

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

Holiday home in Guilford

4.99 out of 5 average rating, 106 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.)

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Holiday home in Southampton

4.73 out of 5 average rating, 37 reviews

Southampton Duplex with private Hotub + backyard

inside this thoughtfully renovated 2 bedroom duplexed cottage you will find hardwood floors, high ceilings, brand new furniture and fixtures and a gorgeous kitchen. Outside you will find a beautiful patio, garden, and deck equally perfect for enjoying your morning coffee or a cocktail after a long day in the private hot tub. while there are two other guest cottages on the property this unit is completely private and sectioned off from the rest of the world. Built for friends and families alike

Guest favourite

Holiday home in Wappingers Falls

4.96 out of 5 average rating, 55 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

Holiday home in Warren

4.98 out of 5 average rating, 175 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

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Holiday home in Carmel Hamlet

4.85 out of 5 average rating, 60 reviews

Serene 4-bdrm lake house

Relax and unwind at this beautiful lake house 1 hr from NYC! 4-season delight: hiking, biking, antiquing, skiing, leaf peeping on the lake-facing deck, snuggling near a toasty fire while looking out a wall of windows, or watching the flowers spring to life. Explore the rugged, hilly town of Kent, sitting atop the interior ridges of the Hudson Highlands, NYC vacation spot since 1920s. A special home, there's so much to do nearby or relax and do nothing at all! (Does not include lake access)

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Holiday home in Miller Place

4.83 out of 5 average rating, 29 reviews

THE MULBERRY OASIS

Bring your family to the custom luxurious mansion on Long Island carefully curated furnishings. No need to lift a finger - wonderfully comfortable and professionally decorated spaces are ready for you to enjoy. Many bespoke items such as a large crystal entry chandelier- custom living room furniture that add unique character and charm. Amazing entertainer's kitchen with gray cabinet. A premier basement with amazing entertainer's, pool table, game table, theater room, exercise /sauna room.

Guest favourite

Holiday home in Torrington

4.95 out of 5 average rating, 222 reviews

Modern/Private Five ★ /Hotel quality stay/1 BR Apt

Enjoy the comfort and tranquility of this modern apt. A lovely space to relax after a busy day. This clean and bright apt offers a tranquil residential vibe alongside quick, easy access to the Torrington downtown areas, restaurants, stores and bars. It features an open-concept layout, a neutral color scheme, wood surfaces, tasteful furnishings and decor. Designed comfortably for your stay offering WiFi, Netflix, laundry, queen bed, well equipped kitchen, and clean fresh white bed sheets.

Guest favourite

Holiday home in New Paltz

5 out of 5 average rating, 49 reviews

☆Mulberry Guest House☆Private☆Walk to village

The Mulberry Guesthouse is a garden apartment with a romantic living room fireplace, cozy den, sunroom, and two bedrooms -- all fully furnished and equipped for easy living while you’re in town. Private outdoor space includes dining table, propane grill, and fire pit. The beauty of our location is the quiet, wooded setting that feels away-from-it-all, but is also walkable to the cafes, shops, and restaurants of downtown New Paltz. Local walking and biking trails are just 2 blocks away.

Guest favourite

Holiday home in Highland

5 out of 5 average rating, 34 reviews

Charming Vacation House w/ Pool & HotTub

Come and Enjoy this House in the Hudson Valley with serene bedrooms & bathrooms, a huge balcony off the master suite with a huge spa tub overlooking the in-ground pool & orchard. The large living room has an inviting stone fireplace, a gourmet kitchen w/ the commercial range, and floor to ceiling doors that opens to the patio & heated pool. Minutes to Hiking, Biking Trails, Farms, Wineries, Breweries & Great Restaurants & Bars. ****Must be the age of 25 to book; ID REQUIRED****

Top Guest favourite

Holiday home in Holmes

5 out of 5 average rating, 23 reviews

The Dahlia Villa within Westerhall Gardens

Reconnect with nature at this unforgettable escape. A gorgeous mature garden in a park like setting. Two queen bedrooms, great room, 75 inch TV. Radiant bathroom floor. Outdoor 45,000 gallon salt pool…that’s shared with other property (summer months - POOL IS FOR REGISTERED GUESTS ONLY - NO EXCEPTIONS) Decompress in our sauna. This a no smoking/vaping property. A sprawling 17plus acre estate. Dahlia Villa is a beautiful two bedroom completely independent unit on the estate.

Top Guest favourite

Holiday home in Hampton Bays

4.9 out of 5 average rating, 20 reviews

Chic 3 bedroom summer get away!

This elegant single family home sits on peaceful neigbourhood highly desirable Hampton Bays , just minutes to ocean, beaches, local restaurants, bars, seafood markets, local farms and jet ski rentals. It’s a perfect location to be at. Either you can enjoy the beach or you can enjoy the minigolf at southampton. If you are foodie there are many delicious restaurants around. We hope you to have beautiful, fun summer memories here :)