Holiday Homes in Fairfield County

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.)

Location · Family · Outdoor spaces

Once in a Lifetime Hudson River Views

Perfect for reunions, retreats, celebrations. Take a deep breath - Riverhouse has space to expand and recharge Watch birds fly, fish jump and trains and ships go by. Hot tub, build a fire (finally hang with your teenager), fly a kite , fish off a private dock. Morning coffee or sunset cocktails on the deck. Play pool, pingpong, or piano into the night. Do a drum circle and dance? YES! No car? No problem. Take direct train (gorgeous ride!) from Grand Central Station, 7 min. walk to the house.

Value · Family · Pool

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

Location · Value · Access

Serene 4-bdrm lake house-no lake access

Relax and unwind at this beautiful lake-view house 1 hr from NYC (private member only lake) 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!

Value · Family · Quiet

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.

Family · Value · Kitchen

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.

Location · Value · Amenities

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!

Location · Family · 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****

Family · Location · Accuracy

The Dahlia Villa within Westerhall Gardens

This is a quiet retreat where you’re with nature at this beautiful escape. A gorgeous mature garden .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.

Family · Location · Nearby

Trumbull Fully Furnished Studio Central Location

Comfortable, Convenient Stay in Downtown Hartford Stay in a fully furnished private apartment located on Trumbull Street in central downtown Hartford. This newly built apartment offers a spacious layout with a queen-size bed, a separate home office, and modern amenities. The building includes access to shared spaces and is designed for a comfortable, no-fuss stay ideal for short or extended visits. Great location with easy access to downtown attractions.

Value · Location · Wi-Fi

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.

Value · Location · Accuracy

High-end 3 bed vacation house across from beach

Stunning vacation house fully renovated from top to bottom. Everything in here is brand new and ready for you to enjoy. Amazing second story outdoor eating and living area. Just steps across the street from the beach in a highly desirable area. 1mile from town with tons of shopping and restaurants.

Family · Location · Amenities