Villa holiday rentals in New Haven County

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.

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

Welcome to Dove Haven, a spacious and serene retreat in Westville, New Haven. Enjoy bright, cozy interiors filled with natural light, a private hot tub, and a peaceful backyard oasis perfect for relaxing or recharging. Tucked on a quiet, tree-lined street, you’re minutes from Yale University and near Edgewood Park. Perfect for: Photoshoots, Interviews, Small commercial shoots, wellness retreat filming, brand content, documentary crew lodging and filming, getaways, group stays, or work trips

The Barn at Bear Burrow 15 Acre Retreat

Welcome to The Barn at Bear Burrow, a beautifully restored tobacco barn where timeless New England character meets Scandinavian-inspired design. Swim in the heated gunite pool, unwind in the cedar hot tub and sauna, or wander private woodland trails across 15 private acres. Discover Litchfield County's farm-to-table dining, tavern pubs, wineries, lakes, skiing, hiking and charming villages –– or simply gather by the fire and savor the moment. A place to return to in every season.

TREETOPS! An upscale, unique 5 bdrm home with POOL

Please find us and book on VRBO thanks!!! 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".

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

Historic Entire Home: Luxury Group Retreat

Experience a blend of history and modern luxury in our 5-bedroom Entertainer's Home. Perfect for large families or groups, it features an open layout, a grand fireplace, a dining table for 12, and a private backyard with a fire pit. Comfortably sleeps your entire group. Located just a short walk from local markets, restaurants, and a lake, with numerous ski resorts and private schools nearby. A perfect retreat for creating lasting memories.

Private Luxury Waterfront Home

With uninterrupted and unequaled coastal views, this home is a haven of tranquility. It sits on a special stretch of the Connecticut coast, with spectacular bird and wild life-watching year-round. Enjoy great shopping in Guilford's boutiques around the historic town green. On chilly nights, you can light the fire in the great room and watch the sun set over the water, then hit the hot tub for some star gazing. A slice of pure heaven.

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