Villa vacation rentals in New Haven County

LuxeCompound-HotTub Pool Sauna Treehouse Gamebarn

Serene, elegantly appointed 19th century compound, fully modernized and set on the edge of a 50 acre land preserve next to boat friendly Bantam Lake. Located in the rolling hills of Litchfield County this expansive home has four buildings and every amenity: pool, hot tub, heated gym, cedar sauna, central AC, 2 chef’s kitchens, game barn, primary suite with wb fireplace and soaking tub, a pool house guest suite with steam shower, & treehouse w/ slides & a swing set built on a 300yr old oak tree.

Value · Location · Hospitality

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

Value · Family · Condition

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.

Location · Family · Amenities

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".

Location · Family · Hiking

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

Family · Location · Hospitality

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.

Family · Location · Hospitality

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

Family · Location · Indoor spaces

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

Location · Family · Backyard