Holiday Homes in Fairfield County

Sweet Silver Sands Beach Studio

Take a break at this peaceful oasis just steps to Silver Sands Beach. Escape to a cozy little studio connected to the back of our house with it's own private entrance. 5 houses to beach. Your own parking spot. The Long Island Sound is the perfect escape to relaxation. 5 minutes away is downtown Milford, a charming New England town, with Metro North train station that runs between New Haven and Grand Central/Manhattan. Be in NYC in about 90 minutes. Shopping 10 minutes away on Boston Post Road.

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.)

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

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)

Weeping Willow Hideaway on the Lake Studio Suite

Private Studio Suite on Mirror Lake. Our NO PET policy is firm due to allergies If you’re bringing a Service dog please let me know Take it easy at this unique and tranquil getaway for relaxing Entire suite with lake access Yard is shared with your hosts Large windows for view of beautiful lake or sit on patio or lakeside for morning coffee Covered picnic area to have a lakeside picnic Hosts live on premises Well water has filtration & water softener Reiki Master Garage parking in winter

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.

Vacation home with pool by the North Fork

Beautiful ranch-style house with modern comforts is waiting for you. Our vacation home (built in 2017) with very high ceilings includes new appliances and luxury furnishings. This home offers 2,300 square feet of space with an open living room, 3 bedrooms and 2.5 bathrooms. The backyard has a swimming pool during the summers and a BBQ grill. (Pool is closed during the winters.) We have a ping pong table and EV charger in the garage. Our home is only 20 minutes away from the North Fork.

Beautiful new private beach house paradise

Experience a private beach in Milford and enjoy a beautiful and spacious new construction fully furnished luxury home! Scandinavian design. Only 4 houses from the best beach in Connecticut. Large outdoor deck with barbecue and tables and chairs for meals and cocktails. Color changing electric fireplace. 4 car automatic garage. Walking distance to ice cream parlors and nature preserve. Rent kayaks and paddle boards down the road. Enjoy your private beach with tide pools at low tide!

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****

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.

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.

Private, modern carriage house. Great for couples.

Newly built in 2022, our charming, modern carriage house is tucked away within a small courtyard garden on a quiet residential street in the heart of Beacon NY. Guests will enjoy an efficient, elegantly designed and furnished interior with views of the Mount Beacon ridgeline from this comfy and private abode. The owners are long-time Airbnb hosts who work hard to ensure their guests have a peaceful, relaxing stay.