Holiday houses in Greater Bridgeport Planning Region

Golden Colonial Home

You will be close to everything when you stay at this centrally-located place. The street is full of life and sometimes noisy. We are minutes away from Seaside Park Beach, Jennings Beach and Saint Mary’s by the Sea. You can make your way to any of our local fishing piers for the best fishing experience in the NorthEast. Our Downtown area is 5 minute drive and it’s full of night life and restaurants. We also have local farms near by great seasonal fruit) depending on the season. Beautiful trails.

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!

Modern Studio Near Fairfield & Sacred Heart Univ

This newly reconstructed downstairs stylish, modern, and spacious studio features a queen bed & a queen pull-out sofabed with remote lighting, luxe bathroom with towels and refillables, a fully loaded sleek kitchen, a 70” TV with surround sound, and guest-controlled ambient lighting. Enjoy a private entrance, in-suite laundry, guest-controlled heat, and ceiling fan. Close to Fairfield & Sacred Heart Universities, shops, beach, and quick NYC transit. Comfort and convenience in one chic space!

Designer Beach Retreat on Exclusive Cedar Beach

Welcome to your own slice of heaven! Enjoy dinner in your Chef's kitchen while watching one of the most radiant sunsets you will ever see. Stunning views from the private rear deck or snuggled on the couch inside the living room. Wade into Long Island Sound with semi-private beach access 250 feet away. The property is 5 doors down from the CT Audubon Society, known for its epic views and wildlife watching. The sunrises & sunsets are beautiful! 15 minutes to Yale. We can't wait to host you!

Enchanting Guest Cottage

Your own cozy cottage nestled away in the most charming, historical part of Fairfield. Where the sounds of the babbling brook lull you to sleep and baby deer peek from behind the lush trees. Serene and enchanting, this 1940s bungalow is bursting with original details and warmth. A one minute drive to the most divine chocolatier, as well as fine dining at Bonda, all your snack needs at the Corner Market. Perfect for a quiet retreat when coming back to nature and beauty fills your soul.

The ARLO - Walk to Brewery & Restaurants

Newly remodeled and designed, The ARLO combines a seamless blend of luxury & comfort for your family. Walking distance to Dockside brewery & stand-out local restaurants, while only 1 mile from the beautiful Walnut Beach. Enjoy a thoughtful & comfortably designed living room, cook in the chef-style kitchen, indoor/outdoor living with a game room and fully-fenced yard. -Less than 2 minutes to The Tyde wedding venue. -15 min to Fairfield U & Sacred Heart -15 min to YALE -0.2 miles off I-95

The River Loft

Escape to The River Loft, a private riverfront retreat in Weston, CT. Built in 2015 by a visionary local architect, The River Loft open-air design seamlessly integrates the outdoors with the interior space. As you step inside this 750 sf small home, you'll be instantly captivated by the layout that makes it feel spacious. Sitting on over 2 acres of forested land with private river access. Book now for an unforgettable experience. For more images & videos visit insta @the.riverloft

Summer Sale! CozyCottage/Pet-friendly/ WalktoBeach

Inspired by my Dad's wanderlust and love of sea & sand. Relax and unwind in this completely remodeled, stylish Cottage a block and a half from Long Island Sound and .9 mile to Walnut Beach - walk to coffee, pizza, lobster shack! We offer a modern kitchen, breakfast nook, dining area, natural stone wall, parking and W/D. Located in a charming coastal town - enjoy quiet neighborhood walks, coastal trails, boardwalk, breweries and restaurants. 15 min to Yale/New Haven, 65 mi to NYC.

Longevity Stay | Gym, Sauna, Red Light, Plunge

Welcome to RO House Fairfield, where luxury, wellness, and connection come together. Designed to help you reset, recharge, and optimize your stay, every detail encourages movement, recovery, quality sleep, and meaningful time with family and friends. Enjoy a private gym, sauna, cold plunge, red light therapy, hot tub, movie theater, basketball court, and outdoor living—all just minutes from Fairfield’s beaches, downtown, restaurants, and the NYC train.

Sunny Fairfield Studio Apartment

Enjoy this sunny, newly-renovated, modern Fairfield studio apartment, located in the carriage building of a historic early 1900's house. Great for an individual, couple, or family. Well situated, a short drive to Sacred Heart & Fairfield Universities, downtown Fairfield and the beach, Silverman's Farm and other Easton farms for apple picking, petting zoos, and the like, and Fairfield Metro Station for a 1 hour train ride to NYC.

Cozy Colonial - Private Hot Tub & Entire House

The way Airbnb was meant to be, something special... a home away from home. No long rule book, just be respectful. Come and stay in this cozy colonial home centrally located in Stratford CT. Walk to the park, soak in the spa, sip tea, listen to music, play games, and relax. Less than 10 minutes from some of the best CT has to offer - beaches, shopping, restaurants, grocery, entertainment, hiking, train to NYC / Yale, and more.

Stylish Sheek Loft Ricport Studio 2, Downtown

Please note location and area before booking!!! (DONT BOOK if you don’t know it’s loud and busy) Conveniently located Downtown in the city of Bridgeport. Feel free to light a fire🔥. Unique hand tinted windows provides the space with an open feel although it is a small space. Queen size bed, fireplace, and aesthetics sets this apartment apart from any rental you can find. *pet fee for pets. Please let me know in advance.