Holiday rentals in Westport

Farmhouse 1899: Minutes to Downtown Westport, CT

Welcome to Farmhouse 1899. This old house is full of charm and history and is the perfect mix of old and new. Every inch of this home has been meticulously designed and furnished by a NYC real estate professional intent on recreating a 19th century farmhouse vibe for today’s modern family. Enjoy easy access to everything from this centrally located home. Close to 2 major highways, a 10 minute walk or 3 minute drive to Downtown Westport where you can enjoy great shops, restaurants and nightlife.

Family Cottage with 4 King Beds and Fire Pit

Escape to Norwalk Cottage, a beautifully designed 4-bedroom, 2-bath home perfect for 8 guests. This family-friendly getaway features a fully stocked kitchen, cozy fireplace, and a fun basement playroom. Relax in the private backyard with a deck, grill, and fire pit. Located on the quiet Norwalk/Westport border, you're just minutes from Calf Pasture Beach, great restaurants, and the vibrant SoNo district. Enjoy central air, fast WiFi, and a dedicated workspace for the perfect year-round escape.

Spacious Westport Apt surrounded by nature!

Spacious mother-in-law basement apartment with private entrance that opens to the backyard. Large windows in every room give view to the creek in the backyard and birds welcoming our guests. Two bedrooms with a queen size bed. Walk-in shower. Plenty of space for up to four people. Very family friendly - little humans and furry friends welcome! Centrally located 8 min drive to downtown Westport, Fairfield, or Southport. Beach, golf course, playgrounds, hikes, wonderful bakeries and restaurants.

Walk to Compo Beach Renovated Westport Home

Unwind in this stunning California-style designer home in Westport. Beautifully decorated, pristine home ideally located close to Westport’s Compo Beach, train and shops. Enjoy one level open concept living, chef’s kitchen with marble counters, high-end appliances, large farmhouse dining table, two comfortable and cozy living rooms, inviting bedrooms, modern baths. Close to Westport’s wonderful restaurants, farmer’s market, downtown shops and beaches. Bonus country shed to lounge in.

Spacious Home Near Beach + Train Sleeps 10+ | Yard

Welcome to our private, clean, centrally located and family-friendly home in the heart of Fairfield County, CT (Norwalk/Westport Border) Why rent a bunch of hotel rooms when you can all be together? This cozy retreat offers easy access to beaches, Universities, Parks, dining, and shopping. Enjoy a peaceful stay with all the comforts of home, perfect for families or small groups. Just minutes from I-95, and Metro-North, it's a great base for exploring nearby Stamford, Westport or NYC.

Whimsical Westport Studio -1 mile walk to downtown

Situated in a prime location that is walking distance to downtown, with a variety of restaurants, numerous designer brand stores, and entertainment venues such as the Levitt Pavilion for Performing Arts. Right of off the Merritt Parkway, I-95, and Westport train station, 10 minutes from Longshore Golf Country Club, Compo Beach, and Sherwood Island State Park. Relax in the homey yet spacious studio with private entrance and patio, shared connected laundry room, and open floor plan.

Nama-stay: sweet Saugatuck Shores beach cottage

Escape to our beautifully curated pink beach cottage in the exclusive Saugatuck Shores neighborhood of Westport, Connecticut. Located on a scenic peninsula and just 150 steps from the water, this charming retreat offers the perfect blend of coastal relaxation and convenience. Watch spectacular sunrises over the water and end the day with breathtaking sunsets. Our neighborhood is ideal for walking, running, biking, paddle boarding, kayaking, and other water activities.

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.

Villa Après Sea

Get ready to play with the whole family at this stylish/private/gated 1-acre Gold Coast house equipped w/ a ping-pong table, fire-pit, grill, swing-set, yard games, & outdoor furniture. Grand great room is adorned w/ an 85” TV & a piano. Stocked kitchen & well-appointed dining room is an entertainer's delight. What vacay would be complete w/o a playroom decked w/ toys? Minutes to: 10: Downtown Westport 14: Compo Beach 15: FairfieldU 39: Yale 70: NYC

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.

Westport Luxury Escape | 10 Minutes to Beach

Tucked away in the historic Old Hill neighborhood of Westport, Connecticut, this unique two home coastal New England property offers a perfect blend of grand entertainment space and private, cozy charm. The listing layout features two distinct structures on a multi-generational, professionally landscaped property, giving you the feel of a private family compound just minutes from downtown Westport and Compo Beach.

Boho Chic Private Home in the Heart of Westport CT

The best of both worlds! Centrally located Westport flat surrounded by greenery and wildlife, tucked in a private neighborhood.. Minutes from Compo Beach, Sherwood Island State Park, Downtown Westport, Downtown Saugatuck, Longshore Golf Course, Nyala Farms, and the Westport Train Station. The perfect place to experience everything Westport has to offer, with the ability to unwind in a relaxing and secluded space!