House holiday rentals in Fairfield

Cape on the Water

Welcome to our Cape on the Water! This unique property is located on beautiful Ash Creek, an inlet off Long Island Sound offering views of tidal wetlands, including tons of fish, bird, kayakers, paddle boarders, small sail boats etc. The house is a newly renovated Cape Cod with an open floor plan, updated Kitchen and bath rooms. Refinished oak hardwood floors through out the entire house. Large deck -great view. The house has a very cozy feel and has been also updated with brand new HVAC system.

Downtown Fairfield 3 bedroom Colonial

Enjoy a charming, 3 bed/2 full bath Colonial that is only a 4 block walk from the coffee shops, bars, and restaurants on the Post Road and .7 mile from the Fairfield Train Station. The house is over 1500 sq. feet on a quiet street and only a mile to the town beaches. Work has taken me from Fairfield, but it remains home, so the house is fully stocked with everything. If you're into shooting hoops, you'll like the lined and paved court. Small well-trained dogs and longer stays are negotiable.

Walnut Beach Escape Fenced Oasis Yard

🌊 Steps from Walnut Beach & Silver Sands State Park, this guest-favorite coastal escape blends beach access, privacy & relaxed luxury. Enjoy a tropical-inspired backyard oasis with a cascading fish pond, multiple lounge areas & a seasonal palm tree—perfect after a day by the shore. Inside, unwind in a beautifully designed home with a gourmet kitchen & modern comforts. Just 90 minutes from NYC & 15 from New Haven, it’s an ideal retreat for beach days, nature lovers & laid-back coastal living.

Private house, Walk to Beach, Train, Town, Theatre

House is centrally located in walking distance to beach, town, Town Green, shopping, restaurants, train, local concerts, and Fairfield Theatre Company. Peaceful backyard nature reserve can be enjoyed from bedroom balcony. Location is great for Family attending University events (celebrations are not permitted at this Airbnb). Convenient storage place for bicycles. Please check "additional rules" on this listing. Toddlers are not permitted for safely concerns but I am always open to discuss

Designer Beach Retreat on Exclusive Cedar Beach

Welcome to your own slice of heaven! Enjoy dinner in your Chef's kitchen while watching one of the most radiant sunsets you will ever see. Stunning views from the private rear deck or snuggled on the couch inside the living room. Wade into Long Island Sound with semi-private beach access 250 feet away. The property is 5 doors down from the CT Audubon Society, known for its epic views and wildlife watching. The sunrises & sunsets are beautiful! 15 minutes to Yale. We can't wait to host you!

The ARLO - Walk to Brewery & Restaurants

Newly remodeled and designed, The ARLO combines a seamless blend of luxury & comfort for your family. Walking distance to Dockside brewery & stand-out local restaurants, while only 1 mile from the beautiful Walnut Beach. Enjoy a thoughtful & comfortably designed living room, cook in the chef-style kitchen, indoor/outdoor living with a game room and fully-fenced yard. -Less than 2 minutes to The Tyde wedding venue. -15 min to Fairfield U & Sacred Heart -15 min to YALE -0.2 miles off I-95

The Cozy Little Cottage

Charming guest apartment on our property on 1.5 acres in pastoral neighborhood, 7 minutes to Wilton center and 8 to Westport center. The cottage is a good size for 1-2 adults, can fit 3 people if one is a child. The unit is separate from our house, connected by a breezeway, above the garage. It is quaint and cozy. High end kitchen appliances include gas range, mini fridge, microwave and mini dishwasher. The bedroom has a queen bed. We have a twin air mattress for use in the living room.

Stareway to Heaven

Welcome to your ideal beachside retreat in Fairfield, CT. This fully furnished 4-bedroom, 3 1/2 bath home offers an open-concept living space, a chef’s kitchen, and a private rooftop deck with stunning coastal views. Just steps from the beach and close to downtown shops and dining, it provides the perfect blend of luxury and convenience. Optional beach cruiser rentals and paddleboards are available. Flexible rental terms are offered for both short- and long-term stays.

Fairfield’s Four bedroom Family Home

When you stay at this Fairfield home, your family will be close to everything! This spacious 4-bed retreat is ideal for comfort, featuring a spacious living room warm fireplace, a modern kitchen, Relax on the front porch or private back deck, perfect for holiday memories. Conveniently located near Jennings Beach, Fairfield and Sacred Heart Universities, plenty of shopping options, bowling alley, restaurants etc. Book your family’s ultimate holiday getaway today!

Longevity Stay | Gym, Sauna, Red Light, Plunge

Welcome to RO House Fairfield, where luxury, wellness, and connection come together. Designed to help you reset, recharge, and optimize your stay, every detail encourages movement, recovery, quality sleep, and meaningful time with family and friends. Enjoy a private gym, sauna, cold plunge, red light therapy, hot tub, movie theater, basketball court, and outdoor living—all just minutes from Fairfield’s beaches, downtown, restaurants, and the NYC train.

Beautifully Restored Barn With New England Charm

Set back from the road on one wooded acre with a brook, this renovated 4-bedroom converted barn pairs rustic New England character with modern comfort. Expect 30-foot ceilings, exposed beams, oversized windows, a babbling brook, large yard, eclectic art and furniture, a grand piano, a stocked kitchen, deck, grill, and space to gather. A memorable Fairfield stay for families, couples, small groups, beach weekends, and quiet escapes.

Cozy Colonial - Private Hot Tub & Entire House

The way Airbnb was meant to be, something special... a home away from home. No long rule book, just be respectful. Come and stay in this cozy colonial home centrally located in Stratford CT. Walk to the park, soak in the spa, sip tea, listen to music, play games, and relax. Less than 10 minutes from some of the best CT has to offer - beaches, shopping, restaurants, grocery, entertainment, hiking, train to NYC / Yale, and more.