Holiday home rentals in Fairfield

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!

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)

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.

☆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.

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!

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.

Your perfect Westport getaway is here!

Great location! Book your stay at the Benjamin on Franklin…walking distance to Westport train & all of the fun Saugatuck bars, restaurants & shops. During the summer, kayaking is only steps away. "Benji" is the newest sister property to popular "Minty" (Araminta on Thames) in Newport, RI. Updated, spacious and comfortable. 2 bedrooms, living room, eat in kitchen & both patio & porch. Sorry but no animals or smoking. No exception. Pls don’t ask.

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.