Vacation rentals in South Central Connecticut Planning Region

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Top-rated vacation rentals in South Central Connecticut Planning Region

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Top guest favorite

Guesthouse in Guilford

4.99 out of 5 average rating, 499 reviews

Get Back to Nature at a Modern Wood Clad Getaway

SPRING IS HERE--Glorious spring birds. Come and enjoy a wonderful time in our guest house--warm days, cool nights. You can Hike on the trails, and Stroll along the ocean. Ospreys; hawks; cardinals, blue jays, bluebirds, gold finches and more are here year round. Great places to shop and eat or catch a show at one of New Haven’s renowned museums or broadway theatres or relax. Enjoy! We want you to have a relaxing stay with us, free from worry. We are located in a private area, away from public.

Top guest favorite

Guest suite in Cheshire

4.93 out of 5 average rating, 148 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

4.87 out of 5 average rating, 15 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

4.93 out of 5 average rating, 46 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.

Top guest favorite

Apartment in Branford

4.96 out of 5 average rating, 26 reviews

Stony Crk Studio ideal for trvl nurses…

Peaceful shoreline studio/retreat ideal for trvl nurses, professors, and professionals—Single occupancy studio comprises upper east-wing of our home—has its own entrance up the exterior stairway with a dbbl-locked interior door and soundproofing for your privacy. Enjoy the balcony views and sunny chaise lounge chairs in rear-garden. Kick off your shoes and totally RELAX in our sleepy niche called Stony Creek, beach and harbor, food and shops pair with historic Thimble Islands tours.

Guest favorite

Cottage in Guilford

4.86 out of 5 average rating, 42 reviews

Your own Thimble Islands private cottage!

Escape to your own piece of private paradise! This unforgettable property encompasses 1+ acres of Narrows Island (Thimble Islands/Old Quarry Peninsula) - accessible by car via permanent land-bridge to island. Spectacular one-bedroom cottage with jaw-dropping surround oceanfront and accompanying views; modern and well-appointed. Approx 20 min to Yale, 5-10 min to town green and shops/restaurants. Indulge in sanctuary on an exclusive piece of Connecticut's most coveted shoreline.

Guest favorite

Home in East Haven

4.9 out of 5 average rating, 10 reviews

Your Home in East Haven

Keep it simple at this peaceful and centrally-located place. Not far from the airport, but far enough that you'll never hear a plane taking off or landing. A short jog away from New Haven and the shoreline, this home is ideal for traveling professionals who prefer privacy and quietude. A fully equipped kitchen, dedicated workspace, and a large porch overlooking a private backyard and open woodlands. The finished basement offers a second bed for those traveling with kiddos.

Top guest favorite

Apartment in Branford

4.99 out of 5 average rating, 115 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

Guest suite in Hamden

4.95 out of 5 average rating, 786 reviews

Large Private Studio + Entrance + Bath

Large beautiful secluded studio with a private entry and private bath. Includes comfy queen size bed, futon sofa bed, free wifi, large smart TV with tons of movies, eat-in table for 4, microwave, mini-fridge, Keurig, toaster, closet w/ iron, and your own dedicated room temperature controls. Located in a beautiful, safe, and quiet neighborhood, the studio is attached to a split level house and located in the back on the lower level. It overlooks beautiful woodlands.

Top guest favorite

Guest suite in Wallingford

5 out of 5 average rating, 600 reviews

Wintergreen Gardens Suite @ William Becroft House

LGBTQ friendly. Our 1915 Arts & Crafts bungalow's spacious in-law suite offers driveway parking, private entrance, sunroom, king bedroom, en-suite bath, kitchenette w/fridge, micro, coffee maker, toaster. Relax in bed with 40" HDTV with Amazon Prime, HBO Max, Netflix, premium cable. Enjoy private gardens to sun, read a book or cup of coffee. Short drive to 4 Vineyards, Theater and the train station.

Guest favorite

Guest suite in New Haven

4.92 out of 5 average rating, 234 reviews

Rustic Two-Story Townhouse Apartment

Rustic two-story Townhouse Apartment connected to Historic New England home located in downtown New Haven. Although the unit is connected to the main house it has its own entrance, kitchen, living room, bedroom and bathroom. It is connected to the main house through a staircase to the basement and a French door. Please note: We have a family cat named Jazz who likes to roam the whole house.

Guest favorite

Apartment in New Haven

4.97 out of 5 average rating, 71 reviews

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.