Villa vacation rentals in Fairfield County

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Top-rated villa rentals in Fairfield County

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Guest favorite

Villa in Southport ( Fairfield)

5 out of 5 average rating, 15 reviews

Designer Villa bordering Westport

This designer cottage is built from the framework of a 300 year old New England farmhouse. The house is next to a forest and a small river, which can be accessed on the property. During the summer guests can enjoy a pool, hot tub, and a quaint natural getaway from city life. During the winter enjoy a cozy setting with a large fire place and a host of games and activities. Located minutes from the beach, Westport's town center, the historic sailing town of Southport and the train station.

Villa in Hopewell Junction

4.84 out of 5 average rating, 31 reviews

Hudson Valley Haven in Hopewell

Relax at Beekman lodging close to many riches of Hudson Valley, only 60mi from NYC. The hot tub runs all year round and the Heated pool is a delight to win hearts from May thru October. Our 3 bdrm home, sleeping 8 guests, is within 20mi of Dia Beacon to the west, Fishkill Ridge trail to the north, snow sports at Thunder Ridge to the east, and the breathtaking beauty of Wappinger waterfalls to the south. We are also a stone’s throw from multiple farms where apple picking and hayrides abound.

Guest favorite

Villa in Wingdale

4.86 out of 5 average rating, 14 reviews

Beautiful farmhouse nature escape 90 min from NYC

Relax with the whole family at this peaceful retreat. Feels far more remote than the short drive (or Metro North ride) from the city would suggest! As you make your way down the long tree-lined private driveway and see the classic house and barn, you can feel the atmosphere shift. Come enjoy our spacious farmhouse with antique charm and modern kitchen/amenities. Walk the path around the property, wander the woods, watch the sunrise over the valley, or go apple picking or skiing nearby.

Villa in Bridgeport

4.75 out of 5 average rating, 8 reviews

Indulge in Prime Luxury 3BR 3-7 Guest

Experience luxury and convenience at our stunning villa! Whether you're planning a group retreat or a family escape, our exquisite property is your ideal haven. Located just moments away from major hospitals, universities, and transportation hubs, our villa provides unmatched accessibility to all your needs. Note: lower level unit listing it might be someone staying/living on the lower unit. They will not be able to disturb or enter the listing separately entrance

Guest favorite

Villa in Bethlehem

4.97 out of 5 average rating, 31 reviews

one red barn.

One Red Barn. A charming 18th century country home located on a picturesque 10 acres, with 6 bedrooms, 2 ponds, a stone courtyard, modern kitchen, formal dining room, heated swimming pool, one red barn, a gazebo and a tree house. Perfect for extended friends and family gatherings. Located 2 hours from NYC and within 30 minutes of the great antiques, shopping and dining of Litchfield county.

Villa in Bridgeport

4.5 out of 5 average rating, 14 reviews

Cheerful 3-bedroom vacation home with fire pit

Kick back and relax in this calm, stylish space. freshly renovated where everything from the fixtures to the furnishings are brand new. This home features a large, fully-fenced backyard, 3 bedrooms, 2 bathrooms, fully appliance kitchen, and popcorn machine with Candy dispenser. As you enter this home, you are greeted by an open concept living room with a 75" smart tv