Family-friendly holiday rentals in New Haven County

Guesthouse Farm Stay

Come stay with us on our historic working farm! Relax on the back deck and enjoy views of our 12-acre property and peaceful pastures. For a more hands-on experience, join us for a tour to get a closer look at life on the farm. Established in 1739, our farm has a rich history in agriculture and livestock. The cozy studio-style cottage features an open living space with combined bedroom, living, and dining area, along with a kitchenette and bathroom with a shower for your comfort and convenience.

Kitchen · Indoor spaces · Access

Luxury cottage by the sea with hot tub and pool

We built this guest cottage to provide an ultimate luxury experience for people wanting to escape from hectic life!With incredible 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. Watch the sun set over the water and relax in the hottub for some night time star gazing year round (pool open June-beg/mid Oct)

Family · Kitchen · Heating

Luxury Rural Barn

Renovated luxury barn on a quiet rural road yet close to all the attractions of Southern Litchfield County. The light-filled barn has two large patio doors into a substantial living and entertaining area with a large sectional sofa-bed, a dining table for 10 and adjacent kitchen area with an island. There is a downstairs washroom. A large light-filled upstairs sleeping area has a king-size bed and a bathroom with shower. Outside is a patio dining area and parking is in the dedicated driveway.

Indoor spaces · Kitchen · TV

Cheerful 3 Bedroom Cottage with Fire Place

We are happy to still offer some dates for September. Come enjoy the solitude of the beach as the tide ebbs & flows. Reconnect with loved ones in this family-friendly place. Enjoy strolls on the beach located just out the back door or a sunset meal on the back porch. This wonderful cottage offers everything you will need during your stay. Including, comfortable beds, beach strolls and a bright upgraded kitchen with many amenities. The 3 bedrooms will fit up to 8 people comfortably.

Family · Indoor spaces · Decor

Modern farmhouse w/ pool, beach, horses and winery

A new, modernized farmhouse with a heated saltwater pool in the heart of North Fork. Nestled on an acre of lush, fully fenced yard, the home can easily accommodate up to 8 guests and all pets! Minutes away from Love Lane (Mattituck's charming downtown), Breakwater Beach (one of best beaches in North Fork), Mattituck train station and surrounding the award winning Bridge Lane Vineyards and picturesque Seabrook Horse Farm, this bucolic home offers the perfect setting for a North Fork getaway.

Indoor spaces · Kitchen · TV

Designer Beach Retreat on Exclusive Cedar Beach

Welcome to your own slice of heaven! Enjoy dinner in your Chef's kitchen while watching one of the most radiant sunsets you will ever see. Stunning views from the private rear deck or snuggled on the couch inside the living room. Wade into Long Island Sound with semi-private beach access 250 feet away. The property is 5 doors down from the CT Audubon Society, known for its epic views and wildlife watching. The sunrises & sunsets are beautiful! 15 minutes to Yale. We can't wait to host you!

Indoor spaces · Family · Condition

Steps to Beach • Hot Tub • Game Room • Water Views

Beautiful coastal beach house directly across from a private beach and tennis club with complimentary guest access. Backing up to a serene marsh with stunning views, this home offers a peaceful, upscale setting perfect for families and groups. Relax in the hot tub with outdoor TV, fire pit, and kayaks. Inside features 4 bedrooms, a workspace, and a new game room with a 100” TV, pool table, shuffleboard, and darts. Minutes from Branford’s town center, dining, and waterfront attractions.

Indoor spaces · Kitchen · Backyard

Cozy 2 Story Cottage in Short Beach Community

A cozy home in a beach community that has a central location with easy access to outdoor activities & local restaurants. The home is also 5 minutes from the Branford Train Station, Stony Creek Brewery, & Branford's town center. We are also a 10 minute drive from New Haven, home to Yale University, Yale Hospital and other colleges/universities. Our guests also gain access to Johnsons' Beach, a private residents only beach, located just around the corner from the home (3 minute walk)

Indoor spaces · Kitchen · Location

Retreat with Heated Pool, 1 Mile to NYC Train

The pool is open for the 2026 season. Escape to a stunning 4-BR home on 2 acres in Redding, CT (#1 Small Town). Just 90 mins from NYC, this luxurious retreat comfortably fits 8 guests. Enjoy hotel-style amenities, a heated saltwater pool, and a gourmet kitchen. Breathe in fresh country air in a peaceful, park-like setting. Perfect for families, offering a blend of modern comfort and outdoor living.

Family · Indoor spaces · Backyard

Apartment in New Haven

This is a luxurious and spacious apartment on the ground floor of a historic home, centrally located in the heart of East Rock. It is a 5 min drive (or 20 min walk) from Yale's campus and there is a shuttle stop right next to the house on Whitney (blue/orange lines). The master bedroom has a king bed and a private shower/bathroom. The guest bedroom has a queen bed and library.

Kitchen · Family · Biking

Midcentury Lakeside Guest Suite

Private guest studio suite in a beautiful, midcentury lakeside home. Built in 1957, this home on a quiet residential street is a unique piece of modern architecture around a serene lake in suburban Connecticut. It is walkable from the nearby railway station, and it is close to West Haven's picturesque beaches, and a short drive from downtown New Haven.

Indoor spaces · Kitchen · Beach

"Red House on the Knoll" at Indian Cove

Ecape to the charming beach community of Indian Cove in Guilford and unwind in this beautifully renovated 1920s coastal cottage. Full of character and warmth, this spacious retreat blends historic charm with modern comfort-featuring wood floors, high beam ceilings, and a stunning stone fireplace that creates the perfect cozy atmosphere year round.

Indoor spaces · Family · Barbecue