Vacation rentals in South Central Connecticut Planning Region

Spacious Oceanfront Getaway with Spectacular Views

Perfect vacation getaway! Awaken to the sun rising over Long Island Sound! Panoramic waterfront views from 70 ft of windows spanning NY to RI. Quiet, private, updated home, NOT a cottage: >2200 sq ft, single level 3B/3B, + bonus lower-level walk-out/office. Master bed double shower/jacuzzi overlooking the water! Multiple oceanfront decks. 100 ft granite shoreline, short stroll to nearby sand beaches. Swim, fish, read a book, or watch the sailboats go by! (Not suitable for children/pets/events.)

Family · Location · Long stay

Family Stays, CT

Centrally located - just 1.2 miles from Wesleyan University, this home offers comfort, convenience, and generous space for groups. With 4 bedrooms across two floors, the layout lets everyone spread out. Bedrooms on separate levels provide natural privacy while still enjoying one shared home. Whether you're traveling with friends, children, extended family, or multiple couples, the 2‑floor setup helps everyone relax without feeling crowded. Ideal for multi‑generational stays and group getaways.

Family · Location · Condition

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 · Walkability

Charm + location. Walk to beach, town, & harbor.

We are sharing our "happy place". Cozy, family-friendly cottage has everything you need to enjoy a lovely vacation in a quintessential New England town. Ideally located between Guilford's famous green, gorgeous harbor and town beach, easily walk everywhere. High-season/weekend rate reflected in general view--check for actual. Recommended for groups of up to 4 (5 if with kids). Second bedroom (king) is open to living area-we provide a folding screen for door area and curtain for “passthrough”.

Location · Value · Cleanliness

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.

Location · Value · Backyard

Waterfront Cottage with access to Owenego Club.

Picturesque waterfront cottage located in the Pawson Park district of Branford, Connecticut. The house is 2400 sqft on .38 acres overlooking the Branford harbor & Long Island sound. During the summer you will have access to a private dock that is a quick boat ride away from the Thimble Island. The house is located close to restaurants, bars and a walking trail. You will also have access to a private neighborhood beach for swimming. Rental includes access to Owenego Beach Club. Pet fee $300

Family · Location · Hot tub

Breathtaking Panoramic Waterfront

Relax to sweeping views from every room in this unique, 4600 sq foot direct-waterfront home with large pool, hot-tub, bar, kayaks, and fire pit. 2 floors of wraparound patio/deck, plus 3rd floor loft and roof patio. Open floor plan, 5 bedrooms (bedroom 5 has separate entrance by pool and is summer only) plus loft, 3.5 bath plus half bath and outdoor shower by pool. (Note: pool not heated and open mid-may to mid-Oct only; hot tub closed after new year until March; parking for 6 cars max)

Family · Location · Comfort

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.

Value · Family · TV

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)

Location · Family · Walkability

Luxurious 3BR Apartment w/ Parking & Gym

Our prime location meets modern elegance. This three-bedroom spacious apartment is designed for comfort, convenience, and sophistication in the heart of a dynamic urban community. Whether planning a quiet night in or a lively evening downtown, Hyatus amenities elevate your living experience. º Rooftop Sky Lounge with an outdoor TV º Screening area º Cabanas º Billiards º Bocce courts º Fireside lounge º Co-working space featuring private work pods º Meeting rooms º Cappuccino Bar

Location · Value · Long stay

Charming home, easy access to everything Branford

Full home, comfortable and very well equipped. Private fenced in backyard with patio dining area. Off-street (driveway) parking. Short Walk to the Shoreline Greenway trail. Less than a mile to downtown, parks, beaches, restaurants, marina, Stoney Creek Brewery. Near event venues, The Owenego and Pine Orchard club. Close to New Haven. Family(kid) Friendly home with private fenced in backyard with patio dining area. Equipped with Pack N Play, highchair, booster seat, etc

Family · Location · Air conditioning

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!

Family · Value · Indoor spaces