Vacation rentals in Westport

S. Norwalk Studio Apt near the water!

Newly-built sunny studio apartment with separate eat-in kithchen and spacious bath, across the street from the water in the peaceful waterfront community of Shorefront Park in South Norwalk. 20 min walk to South Norwalk shops, restaraunts and the train station (65 min train ride to NYC). Private kepypad entrance, washer/dryer, eat-in kitchen, free off-street parking, wifi, central AC. 2 night minimum Please note the house next door may be under construction. Please inquire for current status.

The Colonial Cottage at Fairfield Beach

Historic Fairfield Beach Cottage | Walk to Beach Welcome to our charming Fairfield Beach cottage, a beautifully renovated two-bedroom retreat tucked away on our historic coastal property, just a 10 minute walk or 5 minute bike from Jennings Beach (0.5 miles). Whether you're coming for a relaxing New England getaway, family visit, Fairfield U / Sacred Heart weekend, or business travel, our cottage offers the perfect combination of comfort, conveninece to beach and downtown, and coastal charm.

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.

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.

Waterfront Getaway - Norwalk, CT

Enjoy a stylish experience at this prime location - ideal to explore, relax, or WFH. This beautiful seaside home has full direct waterfront views of the Norwalk Harbor and LI Sound from every room and a balcony. NYC is a quick ride away, with a train station just 0.4 miles away. Across the street is our lovely Veteran's Memorial Park with a route going to Calf Pasture Beach! Experience fine dining in SoNO, long lines at Mr. Frosty's Ice Cream, and more. You won't want to miss this experience.

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.

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.

Wild Rose Cottage (Westport, CT)

Luxurious newly-renovated Cottage in prime location in Westport's historic district. Studio with queen-sized bed, kitchen (w/fridge, dishwasher, stove, oven, toaster, coffee maker), full bathroom, A/C, fireplace, W&D, TV, WiFi. Parking for one car. Back-up generator. Within stone's throw of Hudson Malone, Outpost Pizza, Merritt Country Store, Coffee An' Donut Shop and Grapevine liquor store. Just a short stroll on the sidewalk to downtown Main Street's shops and restaurants.

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.

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.