Holiday home rentals in Fairfield

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.)

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

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.

Private Apartment Loft Style on Pratt and Hartford

Forget your worries in this spacious and serene space. Suite Direct Guests enjoy brand new historical charm with the best-in-class modern conveniences. The private suites are all fully furnished: enjoy a spacious bedroom, kitchenette, private bathroom, workspace, and living area. access to on-site luxe amenity spaces - including shared workspace, game room, media lounge, commercial kitchen, and laundry room - all of which are professionally maintained for ultimate comfort and cleanliness

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.