Vacation rentals in Greater Bridgeport Planning Region

2 bedroom Boathouse

One of a kind boathouse set in the vibrant Dockside marina. (Boat does not move) guests can enjoy the experience of boatlife on the Housatonic River while tied up to the docks. fully equipped head/restroom hot water shower a toilet for peeing only (no #2) #2s at dockside restroom,Beautiful living space, pull out couch sleeps 2, kitchenette, microwave,coffee, refrigerator. 3 outside decks all spectacular views . Master suite, 1 queen bed and couch that sleeps 1. The lower cabin has 2 twin beds.

Lake Hills Suite

Modern architect-designed Suite in the peaceful upscale Lake Hills area of Fairfield. Only 10 minutes from Fairfield and Sacred Heart universities. Close to restaurants & shops. Accommodates up to 4 guests. 1 bedroom with queen size bed; living room sofa pull-out queen bed and a complete kitchenette. Sunny, large private covered balcony to garden. Private entrance and dedicated off-street parking space. Radiant floor heating, central air & ventilation. Washer and dryer in dedicated closet.

Cozy Studio in Bridgeport

Charming and fully equipped studio located in the heart of Bridgeport. Perfect for business travelers, couples, or solo adventurers, this cozy retreat features a comfortable bed, high-speed Wi-Fi, a private entrance, and a fully stocked kitchen for your convenience. Enjoy easy access to local restaurants, cafes, and shops, as well as public transportation and major highways. Whether you’re here for work or leisure, this studio offers everything you need for a relaxing and stress-free stay.

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 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.

Fairfield guest house

Experience timeless charm in this renovated 1915 Dutch Colonial in Fairfield, CT. This spacious two-room unit features a private entrance with a cozy living room and a serene bedroom, both beautifully furnished. Enjoy modern amenities like a coffee maker, refrigerator, and microwave for added convenience. Perfect for a relaxing getaway or visiting nearby colleges and just 10 minutes from stunning beaches. Your ideal blend of history, comfort, and coastal charm awaits!

River Cottage in Weston, CT

Welcome to “River Cottage”, our enchanting private guest cottage in the picturesque town of Weston, CT, nestled on a riverfront property. Located about 45 miles from NYC, and 10 minutes from the lively town of Westport, our two-bedroom cottage is the ideal location for a relaxing few days, a business trip in the area or visiting family and friends. Perched near the tranquil Saugatuck River, the immediate area is a haven for hiking and trout fishing.

Bright, Stylish & Cozy Suite

Welcome to your calm and peaceful retreat — a bright, stylish, and cozy 3rd-floor walk-up suite designed for comfort and relaxation. Enjoy a sunny bedroom filled with natural light and beautiful views that make every morning special. This private space offers a quiet escape from the city buzz, blending modern style with a warm, homey feel. Perfect for those who appreciate calm surroundings, soft sunlight, and a touch of elegance in every corner.

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.

Super cozy 1 BR apt. own entrance, great loc.

Very quiet residential neighborhood, very clean, super cozy apartment with two bedrooms, living room; computer desk with work station, kitchenette (no stove), own bathroom, and amenities. 20 minutes away from Bridgeport, 15 minutes away from Yale, New Haven. Lakes in walking distance, Metro-North rail; 7 minutes, local shopping area 1 mile. Bus route in walking distance. Great neighborhood!! All are welcomed. Warm community.