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!

Family · Location · Cleanliness

Water front studio apartment with fireplace.

This is a beautifully appointed studio apartment located off the patio level of a water front home. Guests enjoy a large private patio over looking gorgeous sweeping views of Long Island Sound. A private entrance and off street parking. The amazing views and amenities make this space the perfect romantic getaway! Close to I95 and Metro North railroad. Ten minutes to great dining in downtown Milford. A true waterfront oasis! Come and experience this beautiful retreat! You won't be disappointed!

Location · Family · Decor

Elegant Modern Stay Near Yale • Gym • Roof Terrace

Come and stay at this luxury, modern one-bedroom apartment just steps away from Yale! Broadway lies 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.

Family · Value · Accuracy

Get Back to Nature at a Modern Wood Clad Getaway

HAPPY SPRING… PEEPERS are singing. The spring birds are arriving and the crocuses are up. Hawks, cardinals, blue jays, bluebirds, gold finches and more are here. Beautiful hiking trails in the woods and along the beachfront. Great places to shop and eat or catch a show at one of New Haven’s renowned museums or broadway theatres or relax. Great restaurants along the shore. Enjoy! We want you to have a relaxing stay with us, free from worry. We are located in a private area, away from public.

Value · Family · Breakfast

Luxury Apt with Parking and Gym | Downtown at Yale

Nestled in the heart of New Haven’s historic downtown, our designer home is part of the city’s most prestigious new luxury complex, renowned for its unmatched amenities and design. Highlights: • Prime location just steps from Yale University • Immaculately cleaned before every stay • Complimentary coffee, plush linens, and premium toiletries • 24/7 state-of-the-art fitness center • Expansive rooftop terrace with grills and chic lounges • Over 700 sqft of bright and sophisticated living space

Family · Value · Indoor spaces

Enchanted Cottage on the Marsh, walk to beach

Enjoy an idyllic stay at Enchanted Cottage on the Marsh! Private, quiet one bedroom cottage on Farm River with breathtaking views from deck. Take in the herons, ospreys and other birds among the natural surroundings while relaxing on your very private deck. Or take a stroll to the neighborhood beach, trails or a restaurant. Enjoy daily retreat from everyday life. We want you to have a relaxing stay with us, free from worry. 10 min walk to beach, trails, 10 min drive to Yale University.

Value · Location · Backyard

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.

Location · Value · Cleanliness

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!

Family · Location · Outdoor spaces

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!!

Value · Location · Amenities

Renovated Studio 1Bd/ 1BA/ kitchen All Private

Escape to a serene place in this one-of-a-kind home, perfectly situated near top New Haven attractions. Enjoy easy access to Lighthouse Beach Park, New Haven Tweed Airport, Downtown New Haven, Yale University, New Haven Yale Hospital, and East Shore Park - all within a 5-mile radius. Plus, get on I-95 with ease. This peaceful neighborhood is ideal for Yale students, travel nurses, and visiting families.

Family · Value · Layout

Guilford Field House

Enjoy a wonderful guest house with all the amenities on a historic property in Guilford, Connecticut. The main house built in 1779 extends its character to the guest house which has views of an open field. On property there is a working restored horse barn. We are minutes to the spectacular downtown area of Guilford and easy access to Durham, Madison, and other surrounding towns and highways!

Location · Accuracy · Condition

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.

Value · Family · Biking