Vacation 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.

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****

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.

UNIQUE and GORGEOUS historic loft style rental

Beautifully bright third floor loft style space with private entry available for your enjoyment. Basic kitchen, laundry, and bath are located on the second floor. Due to the stairs in this unique space, it would be ideal for a single traveler or couple looking for a getaway. Walkable to historic Woodbury, minutes to amazing land trust hiking trails in Roxbury, and only 1.5 hours from NY City.