Vacation rentals in South Central Connecticut Planning Region

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Top-rated vacation rentals in South Central Connecticut Planning Region

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite

Guest suite in Cheshire

4.93 out of 5 average rating, 160 reviews

Cozy & Private Studio Suite

Quiet and private in-law suite. Located close to the center of Cheshire, convenient to Route 10, I-691, and Route 15. Near to grocery stores, great restaurants, and shopping centers. 15 minute drive to Toyota Oakdale Theater, 20 minute drive to Lake Compounce Amusement and Water Park, and 30 minute drive to Yale University, Museums, and downtown New Haven. A slightly longer drive will take you to to the beautiful shoreline, Hammonasset Beach State Park, Foxwoods and Mohegan Sun Casinos!

Guest favorite

Home in North Branford

4.88 out of 5 average rating, 24 reviews

The Gait House at High Gait Farm

WELCOME to "The Gait House" at High Gait Farm. Conveniently located only fifteen minutes from the Yale Campus in New Haven and next door to the Connecticut SportsPlex or take the train into NYC. "The Gait House" can comfortably sleep 6 people. It’s a fully renovated 1840's Farm House. It was once a horse training/boarding farm, however no longer has animals. Feel free to wander the 4.7 acres and peek in the hundred year old barn and get a glimpse of a time gone past. ENJOY YOUR STAY!

Guest favorite

Guest suite in Northford

4.94 out of 5 average rating, 47 reviews

Private Bright Studio Retreat with kitchen

Forget your worries in this spacious and serene space. This inviting space offers a haven of natural light, providing a warm and welcoming atmosphere throughout the day. Whether you're seeking a cozy hideaway, an inspiring workspace, or a versatile entertainment area, this basement retreat offers endless possibilities to suit your lifestyle. With its thoughtfully planned layout and attention to detail, you'll find comfort and serenity beneath the surface in this unique and inviting space.

Guest favorite

Loft in New Haven

4.87 out of 5 average rating, 103 reviews

Cozy Riverside Loft Getaway | New Haven

Escape to this charming Fall Foliage Loft on the Quinnipiac River! With a smart TV, full kitchen, bath, and pull-out sofa, it’s a perfect waterfront retreat. Enjoy autumn sunsets from your private balcony or stroll the colorful marina. Just off I-91, minutes from New Haven’s pizza scene and Lighthouse Point Park. On-site, savor oysters & cocktails at Fair Haven Oyster Co. Rent a kayak or e-boat, or book a charter to explore the river & Sound. Rest, relax, adventure & ENJOY 🍁🔥🍕

Guest favorite

Condo in Hamden

4.87 out of 5 average rating, 132 reviews

Close to Yale Hospital, 1 bed apt, great location.

The offer specially dedicated to travel professionals working in the area of New Haven . Centrally located, best for 2 or one person, one queen bed, access to public transportation with bus stop just 1 min away take you straight to Yale in New Haven , Quinnipiac University, 20 min away to Tweed airport . Easy access to Merritt Parkway and I-91. Self check in with smart lock. No more than 5 min walking distance to Walgreen’s, Domino Pizza, Dunkin Donuts, Eli’s Brick Oven Pizza

Top guest favorite

Apartment in Branford

4.99 out of 5 average rating, 124 reviews

Downtown Branford Retreat - Quiet yet Central Apt

A welcoming apartment nestled in the heart of Branford - a quintessential shoreline community! This inviting space offers modern design, a well-equipped kitchen, comfortable bedroom, and a convenient location. Situated within walking distance of the town green and minutes from beaches, guests can easily explore this vibrant shoreline town. From boutique shops and art galleries to charming cafes and trendy restaurants, experience the best of Branford right at your doorstep!

Top guest favorite

Loft in Guilford

5 out of 5 average rating, 80 reviews

The Studio Apartment at Indian Cove

A unique loft located above a barn garage. Nestled in nature with trees and birds all around. This loft is located in a private beach community. The walk to the beach is 2 blocks. We are located in a very safe neighborhood. Renovated space has high ceilings with windows that are on 3 sides. You will find hardwood floors throughout. The bathroom has a tub/shower with tiled floors and a skylight to let in natural light. Bikes and kayaks are available for your use.

Guest favorite

Apartment in New Haven

5 out of 5 average rating, 17 reviews

Luxury 2BR Apt + Work-From-Home Space

This two-bedroom + work-from-home 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, The Mason’s 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

Top guest favorite

Apartment in New Haven

4.99 out of 5 average rating, 106 reviews

Retreat in New Haven by Stephanie and Damian

Welcome to your personal retreat in the heart of Westville. This apartment has a spacious spa-like bathroom, and cozy living room with an amazingly comfy couch and large flatscreen tv. You will relax in a cloud of comfort in this centrally located oasis, where you'll find yourself near Yale's football stadium, Westville Bowl music venue, local art studios, quaint coffee shops, and famous restaurants just steps from your door.

Guest favorite

Guesthouse in New Haven

4.93 out of 5 average rating, 318 reviews

Square 6ix

Inviting, eclectic, and completely private, this single family stand-alone guest house is an intimate and engaging haven. Stylishly decorated with mid-century modern furniture and adorned with pieces from local artists, this quiet home has a separate entrance, separate porch, high ceilings, and a fully equipped kitchen. The guest house is located a walking-block away from the charms of Westville Village and Edgewood Park.

Guest favorite

Apartment in New Haven

4.95 out of 5 average rating, 41 reviews

Cozy East Rock apartment

A spacious and serene space in the heart of East Rock inside a historic home. 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 private bedroom has a king bed and a shower/bathroom. The sofa in the living room converts to a second bed (queen width) and a second full bathroom (with shower and tub) is located by the kitchen.

Guest favorite

Home in Branford

4.96 out of 5 average rating, 50 reviews

Adorable Beach House on LI Sound

Beach House with incredible views of the Thimble Islands - 4 min walk to Restaurants including Lenny’s, Zagat award winner for fresh local seafood - 1 min walk to Bud’s Fish Market - 3 min walk to Indian Neck Liquor - 3 min drive to brewery w/ food trucks & music - 4 min drive to Branford Green w/ specialty stores, coffee & ice cream