Family-friendly holiday rentals in New Haven County

Amazing views of the Brass City

East Mountain Views at its finest. This clean, 3-bedroom updated ranch is centrally located to highways and shopping centers. Walk out to the back deck and experience some of the best views of Waterbury including Fireworks from the back deck (July). Wi-Fi/cable, central AC/hot air, washer/dryer, and patio furniture/grill (seasonal) are included with the stay. Plenty of entertainment (board games, corn hole, foosball, air hockey) are provided. This house is truly relaxing and will feel like home.

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.

Downtown Elegant Stay By Yale • Rooftop • Gym

Come and stay at this luxury, modern one-bedroom apartment just steps away from Yale! With Broadway just around the corner and some of New Haven’s best Pizza a stone’s throw away you’d be hard-pressed to find a better location for your stay. Enjoy cooking up a nice dinner at home one night using the fully-equipped kitchen provided. Spend the evening on the rooftop terrace watching the sunset over the city skyline before tucking in for the night. Use the downstairs gym for a morning workout.

Bright 1 BR Apt Steps From Yale

Enjoy a bright and cozy 1 bedroom apartment just 2 blocks from the Yale campus and The Shops at Yale. Located in a 3 unit brick building, designated as a property on The National Register of Historic Places, this small renovated 2nd floor apartment maintains the characteristics of the building's original design, while providing all amenities needed for a comfortable stay. Convenient free off street parking provided. Great shops, restaurants, nightlife, and museums can all be accessed by foot.

Stylish & Scenic Escape: Chef's Kitchen ~ Hot Tub

Step into the stylish and peaceful 3BR 2.5BA cabin in a historic Merryall District close to shops, lakes, hiking trails, farms, and downtown New Milford and Kent. Explore the picturesque area and the exciting attractions, or lounge by the fireplace or the fire pit in the magical yard. ✔ 3 Comfortable Bedrooms ✔ Living Room & Sunroom ✔ Wood Burning Hot Tub ✔ Chef's Kitchen ✔ Office/Library ✔ Books, Vinyls & Games ✔ Porch, Yard & Fire Pit ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Laundry See more below!

Gemstone: Family-friendly, Close to Yale/Downtown

Welcome to Gemstone! Nestled on a quiet, tree-lined street, this architect designed space is just minutes from Yale Campus and downtown New Haven. Both beautiful and functional, it has been fully renovated and thoughtfully crafted to feature both modern and classic elements. In addition to two bedrooms and two full bathrooms, it includes everything you need to feel comfortable: central air, washer/dryer, WiFi, a 4-seat breakfast bar, new appliances, easy parking, and a 6-person dining table.

Hartwoods Yurt

Enjoy a unique wilderness getaway and unwind in a peaceful, 10.3 acre wooded environment in our 30’ diameter Yurt, which sleeps 4 in North Guilford, CT. This elevated cylindrical dwelling offers solitude and a large deck with comfortable chairs and forest views. Shaded and cool in the summer with air conditioning and fans available. This Yurt provides a wonderful respite from the hectic world. Perfect for nature lovers with a nearby brook and miles of trails for hiking and mountain biking.

The Cottage on Babbling Brook

A cozy, rustic cottage beautifully overlooking Wimsink Brook. Custom designed & handcrafted woodwork throughout the home. An all around great spot for families and friends. A magical, peaceful and relaxing space. Conveniently located on the Connecticut/New York border, just a 1 ½ hour drive or metro north from NYC. The area is a prime location, as it offers some of the most stunning and scenic hikes & drives in the country. Only a 10 minute drive from Kent, New Milford or Pawling.

Retreat in New Haven by Stephanie and Damian

Welcome to your retreat in the heart of Westville. This apartment features a spa-like bathroom and a cozy living room with a super-comfy couch and large flatscreen TV. Relax in this centrally located oasis near Yale’s football stadium, Westville Bowl, local art studios, coffee shops, and top restaurants just steps away. Perfect for extended stays, traveling professionals, visiting faculty, or anyone seeking a convenient home base this winter. Discounts for stays of 30+ days.

The Winchester House at Science Park-Yale

Located 2 blocks from Yale University's Franklin and Murray College and Ingall's Ice rink, The Winchester House at Science Park is a newly renovated luxuriously appointed 2 bedroom 2.5 bathroom apartment. The apartment features bespoke amenities, free secure off-street parking, snacks and beverages, stylish furniture, 1000 ct. beddings, ample cooking pantry items and everything you need as a guest. Let us welcome you in relaxed luxury!

Cozy Cottage with Fire Pit, near Beach

Escape to Fairfield Cottage, a stylish 3-bed, 2-bath retreat 90 mins from NYC. Comfortably sleeping 8, this sun-drenched home features a private patio with a fire pit, a fully equipped kitchen, and two fireplaces. Perfect for families and just 3 miles from the beach, it's your ideal getaway for relaxation and connection. Enjoy a dedicated workspace, fast Wi-Fi, and numerous family-friendly amenities for an unforgettable stay.

Cozy Private Lake Q Retreat

Escape to a charming lakeside haven! Our cozy 1-bed, 1-bath retreat is a tranquil getaway. Nestled by the water, it's perfect for a romantic escape or a solo recharge. Enjoy stunning lake views, a comfy bedroom, and a serene bathroom. Unwind on the private deck and explore nearby nature trails. A lofted office space with l-shaped desk invites both creativity and productivity. Your lakeside escape awaits! NO CLEANING FEE!