Holiday rentals in Bridgeport
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Top-rated holiday rentals in Bridgeport
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Bird's Nest
Welcome to Bird’s Nest ... A delightful haven nestled in the heart of the Black Rock area of Bridgeport. This home is bathed in natural light and features beautiful craftsman detail. The prime location is within walking distance to serene St. Mary’s by the Sea and the charming Harborview Market. Black Rock boasts an array of great restaurants and shopping. A vibrant social scene and a coastal vibe. The neighborhood is quiet. strict noise ordinance - no loud music or loud gatherings - no smoking!
Cozy, updated single family in Fairfield County
Welcome to your home away from home! Thoughtfully furnished with comfort, style, and convenience, this cozy retreat is perfectly situated for your next Fairfield County visit. Located just one minute from SHU and the Merritt Parkway, you're ideally placed to explore local parks, beaches, shopping, and delicious restaurants. Having personally enjoyed living here, we've crafted a welcoming space with special touches that we’re excited to share with you. Relax, settle in, and feel right at home!
Spacious Cottage Loft
Welcome to the Spacious Cottage Loft! Please enjoy a nice quiet relaxed atmosphere in this unique space. Its a little bit rustic with its shiplap pine and exposed beams. Its a little bit rock and roll with its little music space along with some favorite framed albums hanging on the walls. Very comfy queen size bed. 2 smart TVs (65" up & 55" down) for your entertainment pleasure. Roomy kitchen with brand new appliances. Bath-walk in shower. THIS SPACE IS DESIGNED TO ACCOMMODATE 1-2 GUESTS.
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.
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.
New & Stylish 2 King Bed Apartment w/ Grand Dining
🌟 Modern 2BR Retreat – Renovated & Wheelchair Accessible 🏡 Welcome to your perfect stay! Our newly renovated 2BR apartment offers a stylish and comfortable space for families, business travelers 💼, and couples ❤️. Designed for accessibility, it features a wheelchair ramp for easy entry. Enjoy all the modern amenities you need, plus a prime location near great restaurants 🍽️, shopping 🛍️, and top attractions 🌍. Book now and experience a hassle-free, cozy getaway!
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!
Lavish retreat near downtown
Kick back and relax in this home away from home. Motion sensored lights with spacious waterfall shower unit and outdoor space for dinning and lounge. Full kitchen with multiple tv units(Netflix, Hbo,Hulu, paramount & Starz) and rest areas. Coffee and tea available. 5 mins away from downtown , accessible to trains & bus. Parking available in backyard of property . (Ceiling are low(6’2) due to the space being downstairs ) ( 1 Queen bed, 1 Sofa bed)
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.
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.
New Comfortable Studio Apartment
Make yourself at home and enjoy a completely new space, comfort and tranquility in this great accommodation in East Bridgeport. Located on the 3rd floor of a family house with a separate entrance. 2 minutes by car from I-95, 4 minutes from Metro North Station, 5 minutes to the ferry, 4 minutes to Steelpointe Harbor, 4 minutes to Hartford Health Amphitheater / Total Morgage Arena, 7 minutes to downtown Bridgeport.
Popular amenities for Bridgeport holiday rentals
Other great holiday rentals in Bridgeport
Across from amphitheater Studio
Historic Brownstone Close to Beach & Amphitheater
Golden Colonial Home
Cozy Private Studio | Easy Transit & Beaches
Beautiful home in the town of Fairfield.
Retro Bridgeport Apartment
Walk to Beach, Seaside Park, University
Zen, Spacious & Comfy, Lux beds
When is the best time to visit Bridgeport?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $146 SGD | $146 SGD | $146 SGD | $128 SGD | $155 SGD | $153 SGD | $150 SGD | $154 SGD | $145 SGD | $140 SGD | $141 SGD | $141 SGD |
| Avg. temp | 0°C | 1°C | 4°C | 10°C | 16°C | 21°C | 24°C | 24°C | 20°C | 14°C | 8°C | 3°C |
Frequently Asked Questions
What are the best places to stay in Bridgeport?
Stays in Black Rock, Downtown, and areas near Seaside Park are often suggested for their lively atmosphere and proximity to local dining and waterfront activities. These neighborhoods provide easy access to arts spaces and parks.
What are the best things to do in Bridgeport with kids?
Kids can explore animal exhibits at Beardsley Zoo, run and play at Seaside Park, or enjoy hands-on learning in local museums. Waterfront playgrounds and seasonal events often draw families throughout the year.
What are some of the best things to do in Bridgeport?
Bridgeport has lively arts spaces, waterfront parks such as Seaside Park, and family-friendly attractions like the Beardsley Zoo. Many visitors enjoy shopping at local markets and attending cultural or seasonal festivals.
How is the weather in Bridgeport?
Bridgeport has cold winters near 24–44°F (-4–7°C), and warm, humid summers averaging 67–83°F (19–29°C) with occasional rainfall. Spring and autumn are milder, with comfortable temperatures and changing foliage.
When is the best time to visit Bridgeport?
Late spring through early autumn is often recommended for visitors who prefer milder temperatures and outdoor events. Winter brings colder weather and indoor arts activities, while autumn features colorful foliage and community festivals.
What are the best places to visit in Bridgeport?
Bridgeport has family-friendly attractions like the Beardsley Zoo, waterfront parks, and museums highlighting local history. Many visitors enjoy the creative atmosphere at art galleries, and quiet moments in green spaces around the city.
What are some hiking trails in Bridgeport?
Bridgeport has walking and nature trails in places like Beardsley Park and Seaside Park, with views of woodlands and waterfront areas. Nearby nature preserves offer additional paths for birdwatching and exploring the outdoors.
What are some family activities we can do in Bridgeport?
Families can explore Beardsley Zoo, enjoy picnic spots and playgrounds in Seaside Park, or discover hands-on exhibits at local museums. Seasonal festivals, outdoor concerts, and waterfront activities are also frequently suggested.
What are some of the best day trip ideas from Bridgeport?
Many visitors explore quieter beaches near Long Island Sound, art galleries and shops in nearby towns, or forested hikes in regional parks surrounding Bridgeport. Seasonal activities, local farms, and outdoor trails are frequently suggested.
Are there any pet friendly accommodations available in Bridgeport?
Many vacation rentals in Bridgeport are pet friendly, allowing visitors to stay with dogs or cats. Neighborhoods such as Black Rock and Downtown frequently have welcoming spaces near parks and walking areas.
What are some local tips for visiting Bridgeport?
Locals often suggest exploring the waterfront early in the morning for a quieter experience, and attending neighborhood markets or festivals to sample diverse foods. Public transit and walking are convenient for moving between popular attractions and parks.
What is Bridgeport known for?
Bridgeport is known for its historic waterfront, diverse arts and music communities, and Connecticut’s only zoo. The city also has locally rooted culinary traditions and a strong history in manufacturing and innovation.
What are the best hidden gems to explore in Bridgeport?
Bridgeport has smaller galleries, murals by local artists, and community theaters that highlight creative voices in the city. Waterfront trails in less crowded parks, and neighborhood bakeries featuring Portuguese and Brazilian treats, are often favorite discoveries.
What are the best foods to try in Bridgeport?
Bridgeport’s food scene features locally rooted favorites such as New England–style pizza, fresh seafood, and Portuguese baked goods. Many visitors enjoy exploring casual restaurants and bakeries around the Black Rock neighborhood.
What should I bring for a trip to Bridgeport?
Pack comfortable walking shoes, weather-appropriate clothing, and a light waterproof jacket. If visiting in summer, sunscreen and water bottles are helpful for outdoor activities; in winter, a warm coat and gloves are suggested.
What is the nightlife in Bridgeport like?
Bridgeport has a mix of laid-back bars, music venues, and performance spaces, especially around Downtown and the Harbor area. The scene features live music, occasional comedy nights, and locally inspired cocktails.
What are the most popular events or festivals in Bridgeport?
Bridgeport has lively arts, music, and cultural festivals, often focused around areas such as Downtown and the waterfront. Events like outdoor concerts at Seaside Park are frequently suggested, highlighting local traditions and a wide mix of performances.
Are there family friendly vacation rentals in Bridgeport?
Bridgeport has a variety of family-friendly vacation rentals throughout areas like Black Rock, Seaside, and Downtown. These neighborhoods typically have easy access to parks, playgrounds, and local attractions.
Quick stats about holiday rentals in Bridgeport
Total holiday rentals
Explore 320 holiday rentals in Bridgeport
Nightly prices starting at
Bridgeport holiday rentals start at $26 SGD per night before taxes and fees
Verified guest reviews
Over 7,930 verified reviews to help you choose
Family-friendly holiday rentals
140 properties offer extra space & child-friendly amenities
Pet-friendly holiday rentals
Find 80 rentals that welcome pets
Holiday rentals with a pool
10 properties feature pools
Rentals with dedicated workspaces
190 properties have a dedicated workspace
Wifi availability
310 of Bridgeport holiday rentals include wifi access
Popular amenities for guests
Guests love Gym, BBQ grill and Laptop-friendly workspace across Bridgeport rentals
4.7 Average rating
Bridgeport stays receive an average rating of 4.7 out of 5 from guests
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