Pet-friendly holiday rentals in Fairfield County

1956 House of the Year Award. Easy commute to NYC.

Architectural masterpiece, designed by famous architect Ulrich Franzen. House of the year awarded in 1956 by Architectural Record, featured in LIFE and House and Garden magazines. Taste the unique experience of modernist living, surrounded by nature yet walking distance to the beautiful town of Rye, the beach, natural parks and 45m by train to NYC. The house is filled with light,all the rooms have forest views,you feel inmersed in nature while enjoying the magical experience of modernist living!

Walkability · Pets · Nearby

Private Guest Suite | Entrance, Bath & Parking

Private guest suite with a private entrance, attached bathroom, dedicated workspace, fast internet, and private parking. Located on a quiet 1.5-acre property in Wilton, CT, walking distance of ASML and close to Norwalk Corporate Park, downtown Wilton, restaurants, coffee shops, stores, parks, and the Norwalk train station. Owners live in a separate part of the house. Guests have private access and space. Pets are welcome, outdoor space for dog walks. Cats live here but do not enter the suite.

Pets · Walkability · Back garden

1BR full cottage, 1 min walk to private beach

Enjoy time at this lovely studio located in the heart of Rowayton, a charming New England seaside village bounded on one side by Long Island sound and the other by a tidal inlet. Based in the southwest corner of CT, we are just a 1 minute walk to 2 separate and secluded beaches as well as 2 private, well manicured parks. Great amenities in town including tennis, sailing, outdoor yoga, sunbathing, plus nice restaurants. Pedestrian and dog friendly town; you don't even need a car while here.

Pets · Walkability · Air conditioning

Nature Retreat Airbnb

House located in beautiful and tranquil Redding, CT. Two floors with private deck. Main level: half-bath, cook's kitchen with a 4-person dining area, living room with flatscreen TV with an Apple TV and a view of nature. Living room convertible couch can sleep two small children or one adult. Upstairs: 2 bedrooms with full size beds, privacy blinds, bathroom w/ shower (no tub). If you want a getaway from the city, or just an escape then come to this quiet and private house in the woods.

Outdoor spaces · Pets · Access

Comfortable home away from home- near everything

Price includes Airbnb fees. Cozy, pet-friendly cottage in a peaceful setting just 70 miles from NYC and minutes from I-84 (Exit 8 or 9). This clean & comfortable retreat features 3 bedrooms (2 queens, 1 full), and pull-out couch. Portable A/C's in summer, and fireplace for cozy nights. The greenhouse adds plenty of natural light, the yard is perfect for kids, the front deck is great for morning coffee, and the gas grill great for cooking out. High-speed WiFi and 3 smart TVs.

Outdoor spaces · Pets · Location

The Cove Cabin

An original Candlewood style cabin. The house has been updated to offer all modern comforts. It features a large fireplace in the living room, porch over looking the lake, central heat and air conditioning and a fully equipped cook's kitchen. It is on the northern most part of Candlewood Lake with direct, private water access from the shore or the dock. A foam lily pad, two SUP, and two two-person kayaks are available for use from May 1 to November 1.

Walkability · Pets · Beach

Historic Loft, Co-Work, River View

Unique studio loft in a beautifully restored 19th-century Cider Mill on the Westport/Southport border. Enjoy picturesque river views, historic charm, and modern comfort. This pet-friendly retreat comfortably accommodates up to three guests, featuring a full kitchen, dedicated workspace, and access to a co-working space. Ideal for couples or solo travelers seeking a blend of history, convenience, and a serene setting with private parking.

Walkability · Pets · Parks

Peaceful Light-Filled Guesthouse salt pool/sauna

Step into a peaceful, well-appointed home nestled on 14 acres of ancient trees, stone walls, and meadows in Pound Ridge, NY. This light-filled guesthouse is designed for relaxation, with a heated saltwater pool available in summer, sunbathing under a majestic maple tree, and evening stargazing by the outdoor fire pit, or unwind in the pool side sauna.. Perfect for families, small groups, or couples seeking a peaceful nature retreat.

Outdoor spaces · Walkability · Condition

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.

Walkability · Outdoor spaces · Nearby

Renovated Cape Near beach, with Fire Pit and BBQ

Beautifully renovated 3-bed, 2-bath home perfect for families or groups of up to 9. Features a cozy fireplace, fully equipped kitchen, dedicated workspace, and a patio with a fire pit & BBQ. Located in a quiet neighborhood minutes from Fairfield University and Fairfield beaches, this bright and inviting space is your ideal retreat. Enjoy modern amenities and a seamless self-check-in experience.

Walkability · Outdoor spaces · Cleanliness

Cozy, romantic cabin by the lake.

This romantic, rustic and cozy lakeside cabin is the perfect place to unwind, relax and explore nature. There are miles of woodland trails to explore, and it is only 55 minutes from NYC, 5 minutes from the Merritt Parkway and other major highways, 20 min UBER from Metro North Train Fairfield Station, or Bridgeport.

Pets · Outdoor spaces · Quiet

Cozy Cottage by the pond

This sweet little cottage on our pond is your perfect mini vacation with direct access to one of CT's best kept secrets, Huntington State Park is steps away. Peaceful and quiet you can also hike, bike, kayak, x/c ski and explore the countryside.

Pets · Outdoor spaces · Condition