Holiday houses in South Central Connecticut Planning Region

The Gait House at High Gait Farm

WELCOME to "The Gait House" at High Gait Farm. Conveniently located only fifteen min from the Yale Campus in New Haven and next door to the CT SportsPlex or take the train into NYC. "The Gait House" can comfortably sleep 6 people. There are three bedrooms and two full baths. Upstairs one bedroom has a king bed & the other bedroom has a queen bed. There’s a full bath upstairs as well. There’s a bedroom on the main floor w/a king bed. A shared full bath is on the main floor. ENJOY YOUR STAY!

House Near Yale, Fire Pit & Garage, Group Family

Enjoy a peaceful stay in this thoughtfully renovated home blocks from Yale Divinity School and Canal Trail. Situated on pedestrian-friendly streets in a welcoming neighborhood, the entire property offers exclusive access for your stay. A covered garage-to-kitchen walkway makes arrivals and unloading easy in any season. The primary bedroom includes an en-suite bathroom, while central AC provides personal comfort. Relax in the backyard with a patio and fire pit—your perfect haven after a busy day.

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.

The Garden Loft - A Charming New England Stay

Welcome to The Garden Loft! Located in the heart of downtown Wallingford, CT. This traditional and historic New England carriage house has been completely renovated in the summer of 2022 into a peaceful, cozy, bright & airy loft. We are a 3 minute walk from downtown where you will find a variety of restaurants, bars, a brewery & only 1 mile from from Choate Rosemary Hall. A 15 minute drive to Yale University & downtown New Haven. Get ready to relax, get cozy & enjoy The Garden Loft!

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)

Stedley Creek

Slip into a slower pace in the seaside village of Stony Creek, where quiet coastal charm meets refined comfort. This private one-bedroom retreat offers a serene, light-filled escape designed for relaxation. Attached to a larger home yet completely separate with its own entrance, the space feels peaceful and intentionally curated — perfect after a day by the shore. Enjoy a tranquil waterfront setting just minutes from I-95, downtown Branford, and a short drive to New Haven.

Basecamp Bluffs

Welcome to Basecamp Bluffs - a cozy, rustic yurt tucked beneath scenic ridgelines and surrounded by forest and endless trails. Perfect for hikers, couples, solo travelers, and nature lovers looking to unplug, recharge, and reconnect with the outdoors. Wake up to birdsong, breathe in fresh air, and spend your days exploring miles of scenic trails and local sites. Simple comforts, stunning views, and peaceful seclusion make this the perfect basecamp for your next adventure.

The Connecticut Cottage | Historic Modern Charm

Welcome to The Connecticut Cottage — a beautifully restored 1790s stone cottage blending historic New England charm with modern comfort. Thoughtfully renovated from top to bottom, this one-of-a-kind home offers the perfect mix of cozy escape and central convenience along the Connecticut shoreline. Whether you're planning a laid-back coastal getaway or exploring some of New England’s most iconic destinations, you’re perfectly positioned!!

Peaceful Farm Country Getaway

Relax in our peaceful and private attached apartment, where you can look out the window to see birds and deer nearly every day. There are hiking trails with amazing views just down the street and this is also a beautiful area for jogging or bike riding. Visit downtown Guilford for shopping at the charming Guilford Green or walking around the Guilford dock. Just 30 minutes from Middletown or New Haven and 45 minutes from Hartford.

Cupola Hill -a 2 BR guest suite with bucolic views

Beautiful 2 bedroom guest suite attached to main house with separate entrance, bathroom, living room. Set on magnificent 20 acre estate, perfect country get away, only 15 minutes to Yale and downtown New Haven. It’s the best of both worlds! Come enjoy the great restaurants of New Haven and then head to Cupola Hill for an evening in the country! Have a glass of wine under the stars and watch the wildlife!

Wooster Retreat | Pizza | Boho

Want to smell the pizza from your front door? The Wooster Retreat is a comfortable, modern & Boho fusion 1 bedroom that is steps from the best pizza in the world. Intentionally designed and well-equipped above and beyond, massive kitchen opening into the living space! Conveniently close to everything: 10 minute walk to downtown New Haven, Yale, restaurants, bars, train station, and art museums.