Villa holiday rentals in New Haven County

TREETOPS! An upscale, unique 5 bdrm home with POOL

*Please find and book us on the site that begins with a V!* TREETOPS is a 4850 square ft 5 bedroom house perched on an outcropping of granite cliffs, on 2 acres of beautiful forest. *Property not suitable for children under 8 years old* Sit in the garden, have a fire in the fire pit, or relax and get some sun by the marine-blue, stone-decked pool! Birdwatching, breakfast, and evening cocktails are best on the spacious wrap-around deck. Hiking is just steps away at "Westwoods Trailhead".

Cottage in Silvermine: Norwalk New Canaan Wilton

Nestled in a leafy Norwalk neighborhood filled with historic houses, this newly remodeled charming guest cottage/Barndominum on 1 acres in opposite the Silvermine river (where New Canaan, Wilton, and Norwalk meet). The guest cottage is separate from the main house. It is a quaint, quiet and cozy. 1 bedroom 1 bathroom new kitchen including range, dishwasher, Keurig and washer and dryer. The bedroom has a queen bed and the living room has a sofa and chairs. Twin cots can be brought in.

Luxury Riverfront Estate | Pool, Spa & Tennis

Welcome to The Well Maiden. A private, luxury riverfront estate designed for unforgettable group stays, where two streams wrap around the home and flow just steps from the living spaces. This one-of-a-kind retreat blends a restored 100-year-old wing with striking architectural design, offering a heated pool and spa, private tennis court, and seamless indoor-outdoor living. Ideal for family gatherings, celebrations, and quiet escapes into nature, just two hours from NYC and Boston.

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

A Spacious 5BR Near Yale | Ideal For Groups&Family

Welcome to Dove Haven — a peaceful and stylish retreat in the heart of Westville. Relax in the private hot tub, enjoy cozy sun-filled spaces, and walk to charming cafés, top restaurants, and beautiful Edgewood Park. Just minutes from Yale and downtown, this spacious home offers warmth, comfort, and good vibes — perfect for families, groups, and work trips seeking a relaxing escape.

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

Charming Country House with Pool, HotTub & Gardens

A beautiful respite in the hills of Connecticut. 2.5 acres of quiet space in the country. The pool, hot-tub, fenced-in yard, patio, wisteria-covered pergola, and charming barn make this the perfect get-away from the city! Hot Tub is open April-December (Heated) Pool is open May-October (Not Heated) Pets allowed on a case-by-case basis