Holiday houses in South Central Connecticut Planning Region

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Top-rated holiday rentals in South Central Connecticut Planning Region

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Top Guest favourite

A spacious deck features multiple blue Adirondack chairs, all facing the tranquil waters of Long Island Sound. The horizon showcases a gentle gradient of pastel colors, signaling the transition from day to evening, while the calm water reflects the serene atmosphere.

Holiday home in Guilford

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.)

4.99 out of 5 average rating, 149 reviews

Top Guest favourite

A charming two-story farmhouse is depicted with a white exterior and a brown-shingled roof. The front porch is furnished with two chairs and includes a decorative lantern. Lush green grass surrounds the house, providing a serene setting amidst the trees.

Home in North Branford

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!

4.94 out of 5 average rating, 49 reviews

Top Guest favourite

The sunroom features a light pink wall and a high ceiling with exposed beams. A comfortable wicker sofa with decorative throw pillows accompanies two matching chairs. A patterned area rug covers the floor, while a small table sits in the center. Soft light filters through sheer curtains.

Cottage in Guilford

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”.

4.94 out of 5 average rating, 310 reviews

Top Guest favourite

An expansive patio extends towards the shimmering waters of Long Island Sound, featuring lounge chairs and a dining table with an umbrella. Decorative planters and lanterns are arranged along the patio edge, complementing the serene waterfront view.

Apartment in Milford

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!

4.97 out of 5 average rating, 651 reviews

Top Guest favourite

A comfortable living area features a light-colored sofa, two leather chairs, and a wooden coffee table. A flat-screen TV is mounted on the wall, with decorative artwork above it. Soft curtains frame the windows, allowing natural light to fill the space.

Apartment in New Haven

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.

4.99 out of 5 average rating, 123 reviews

Guest favourite

A cocktail is presented in a tall glass with a vibrant green stem, garnished with red berries. Sunlight glows in the background, reflecting off the water. A white adirondack chair is visible nearby, set against a tranquil evening scene.

Home in Branford

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)

4.93 out of 5 average rating, 46 reviews

Top Guest favourite

Home in Branford

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.

4.99 out of 5 average rating, 113 reviews

Superhost

Cottage in Branford

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)

4.85 out of 5 average rating, 271 reviews

Guest favourite

A cozy living area features mid-century modern furniture, including an orange armchair and a sleek glass coffee table. A gallery wall displays various artworks, complemented by natural light from two windows. A small dining area with a round table and four chairs contributes to the inviting layout.

Guesthouse in New Haven

Westville Hideaway | Stylish Guesthouse + Parking

Inviting, eclectic, and completely private, this single family stand-alone guest house is an intimate and engaging haven. A serene private guesthouse perfect for couples, creatives, and travelers. Stylishly decorated with modern amenities, this space is a cozy retreat just a short walk to Westville Village and Edgewood Park. Ideal for weekend getaways, local visitors, or professionals seeking a quiet base with fast WiFi and free parking.

4.91 out of 5 average rating, 357 reviews

Top Guest favourite

A bright and modern kitchen area features white cabinetry and stainless steel appliances. A large island is equipped with seating for three, while a cozy living space with two leather chairs is visible in the background. Natural light filters through multiple windows.

Apartment in New Haven

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!

5.0 out of 5 average rating, 209 reviews

Guest favourite

A cozy sleeping area features a wooden bed frame adorned with decorative pillows, flanked by two bedside tables. A light blue throw is draped over the bed. A comfortable seating area includes a round table and armchair, complemented by a soft rug covering the floor.

Apartment in New Haven

Modern Urban Getaway | Near Yale + Downtown

Beautiful and private Airbnb apartment located in New Haven. Peaceful, bright, immaculate and thoughtfully appointed is the best way to describe the Urban Sanctuary. You will fall in love with our cozy and charming garden apartment, nestled in a historic 3 family home in Westville. You will find good restaurants and coffee shops around, it's just the best place for you to stay. We provide a variety of amenities.

4.93 out of 5 average rating, 355 reviews

Top Guest favourite

Guest suite in New Haven

Charming Studio w/ Private Entrance & Free Parking

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.

4.95 out of 5 average rating, 223 reviews