Vacation rentals in New Canaan

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.

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.

Serene Pond Views Charming private patio…

Country Charm Awaits. 45 miles north of George Washington Bridge. Our 2 room efficacy apartment w. microwave, mini fridge & private entrance + parking space. Great WiFi, Apple TV. Enjoy views overlooking Henderson Pond. 1/4 walk to Query State Park, 36 acres w. trails. Our apartment is 4 miles from town of Ridgefield, 3 miles from Wilton town center, 6 miles from New Caanan & 8 miles from Westport Town Center. We have a couple of small puppies who will welcome you too. So we don’t allow pets…

Sunny French Cottage

This unique, sunny cottage has it's own style. Private and peaceful, completely renovated cottage with French vibes. Originally used as a painting/design studio. It is an ideal place to relax and enjoy the surrounding nature. The upstairs bedroom is loft style and has a luxurious queen size bed. It's ideal for short and long stays. It is a perfect place for cozy evenings and lazy mornings, it can also serve as a temporary workplace. High tea style, organic breakfast available (20$ per person)

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.

5BR Beach House, Game Room + Huge Backyard

Escape to this spacious 5-bedroom Shippan beach home, designed for families and groups to relax, reconnect and have fun together. Just a short walk from West Beach, the home features a huge private fenced backyard, two large decks, fire pit, game room, pool table, ping pong, foosball and plenty of indoor and outdoor space for everyone to spread out Located just minutes from Downtown Stamford and Metro-North, it’s an ideal home base for family getaways, group stays and corporate retreats

Peaceful New Canaan 2-BdRm Cottage - Pet Friendly!

Relax and recharge at this unique and tranquil cottage, situated on 2.5 acres of land with two ponds. Pets welcome! Property is fully fenced in. 2 bedroom guest house is next door to the main house, with separate driveway. Parking for up to 4 vehicles. High speed fiber internet, advanced water filtration system, washer/dryer, dishwasher, and automatic motion sensor exterior lighting around the property. Central heating and air conditioning, with thermostat on each of the 3 levels.

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.

Spectacular Renovated Barn

Make memories at this unique and family/group -friendly place. Professional chefs kitchen, outdoor patio and large fenced in yard - very pet friendly. This dramatic home is a perfect retreat / multi-family. Quite street. Great open space for cooking and socializing. Soaring 11-foot ceilings, antique wood beams, working fireplace and walls of glass that flood the interior with natural light, historic character with contemporary functionality.

Private cottage in horse country &1 hour from NYC!

Private cozy cottage located in horse country on the the NY/CT borders ( New Canaan, Ridgfield, Wilton ) It is a perfect quiet getaway for couples or a friends night out , a great pit stop for travelers /skiers , fine dining , shopping /antiquing , Ridgefield Playhouse , hiking ,and a short ride to Grace Farms . 1 hour train ride to NYC . We provide organic fruit,breakfast snacks, coffee and tea . It is your home away from home and more :)

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.

Cozy cottage in the village of Pound Ridge

This recently renovated luxury apartment is all yours, steps away from lively Scotts Corners, with restaurants, grocery, shopping and more! No car necessary! But there is plenty of parking and even an EV charging source, for your use. Scotts Corners is the one block business district of picturesque Pound Ridge. Weekend events in this wonderful town are the norm: Food Trucks, musicians and flea markets.