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Holiday houses in Bridgeport

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Top-rated holiday rentals in Bridgeport

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

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Top Guest favourite
A rustic barn-style home features a wooden exterior with multiple large windows, enhancing natural light. A spacious elevated deck is surrounded by lush greenery, while an outdoor umbrella offers shade. The setting is serene, with a glimpse of the nearby brook and wooded area.
Home in Fairfield
4.96 out of 5 average rating, 337 reviews

Luxurious Barn With New England Charm

Three decades of tasteful renovations — many using re-purposed material — have rendered this converted barn magazine-worthy. Set-back from the road on 1-acre of wooded land with a babbling brook, this conveniently-located modern home maintains its rustic allure. With 30-foot ceilings, exposed wooden beams, dozens of windows, an array of eclectic furniture, and a grand piano, the charm of the barn is immediately obvious. Perfect for romantic getaways, small retreats, family gatherings, and more.

Guest favourite
The living area features a neutral color palette with a contemporary couch and a low coffee table. A bar-style dining area with high stools is visible, complemented by a 42-inch Roku TV mounted on the wall. Natural light enters through a window, enhancing the inviting ambiance.
Apartment in Norwalk
4.91 out of 5 average rating, 357 reviews

The Seasons Luxe Pad 1 Bedroom | Center of Norwalk

The Space Private one bedroom apartment with a modern decor offers everything you need for a short or long term stay. Space includes a separate living/dining area and New York City inspired artwork. Bedroom offers a Queen Sized bed, desk, 40 inch Roku Smart TV & plenty of closet space. The Location Half mile from I-95 & near Merritt Parkway, South Norwalk train station, South Norwalk downtown and a half mile away from the Norwalk Hospital. Minutes away from shopping centers and grocery stores.

Guest favourite
A spacious bedroom features a king bed with a soft green duvet and decorative pillows. Two nightstands with lamps are positioned on either side. Natural light enters through two windows adorned with bamboo shades. A framed coastal artwork is displayed above the headboard.
Guest suite in Fairfield
4.93 out of 5 average rating, 183 reviews

Adorable private apt w/ W/D in lovely neighborhood

Enjoy a lovely experience at this centrally-located studio in-law apartment. It boasts a newly renovated kitchen and bath, king bed with brand new mattress, pull out full size sofa, ample closet space and more. The eat-in kitchen has all you need to feel right at home. The apartment is located adjacent to a nice residential house, but is fully private with your own front and back entrances. There are also no stairs, making it easily accessible. It’s located in a wonderful neighbor in Fairfield.

Guest favourite
A spacious backyard is visible, featuring well-maintained greenery and shading trees. A patio area made of paving stones extends towards the house, with a small table and grill positioned nearby. Bright sunlight filters through the surrounding foliage, creating a serene outdoor setting.
Home in Fairfield
4.86 out of 5 average rating, 111 reviews

Bright 3-bedroom house with ample parking & patio!

Take in the sunshine at this peaceful & fully renovated Fairfield home! Private property in a gorgeous neighborhood, this house is a 10-min drive from Fairfield University & 7-min drive from Sacred Heart University. Right next to the Brooklawn Country Club. Central A/C, lots of natural light, large back patio & fire pit, washer/dryer, dishwasher, and strong Wi-Fi with Roku TV in both living room & family room. Public beach access available, highly-rated eateries, & tons of shopping nearby!

Guest favourite
A comfortable living room is featured, with a gray sofa and two wooden chairs positioned around a small, circular coffee table. Natural light filters through large windows, illuminating light-colored walls and warm wooden flooring.
Home in Milford
4.99 out of 5 average rating, 150 reviews

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

Superhost
Guest suite in Fairfield
4.87 out of 5 average rating, 126 reviews

Fairfield 2nd Floor · 2 Rms · Full Bath · Parking

ENTIRE 2nd FL for up to 2️⃣ adult guests ONLY 2️⃣ Rooms➕Skylit Full Bathroom Exclusive Driveway Parking➕locked entrance leading airbnb, separate from full-time renters on 1st FL Heat & Cool: wall-mounted AC➕portable Dyson ➕ Central AC w/2 sensors - host adjustable remotely TV is Screen only, works with Bluetooth & Chromecast, NO Services Kitchenette: heat/store food (NO cooking), allows affordable stay in affluent Fairfield Town Professional Clean Service Host Assistance Virtually

Guest favourite
A cozy living area features a dark, comfortable couch and a decorative rug. A wall-mounted television is positioned above a simple mantel with a potted plant. Natural light filters through floral curtains, illuminating a wooden desk and chair against the wall.
Apartment in South End
4.89 out of 5 average rating, 119 reviews

Seaside Studio in Historic Bridgeport Brownstone

Keep it simple at this peaceful and centrally-located historic brownstone built by P.T. Barnum for his staff 140 years ago. Basement unit across the street from Bridgeport University, 1 block to Seaside Park and beaches, 5 min walk to amphitheater, and 10 min walk to Metro North or LI ferry. Includes kitchenette with fridge/freezer, microwave, stove and oven, desk, couch, wifi, tv with Roku , iron, hairdryer, and full bathroom. We are pet friendly up to 2 with additional $25 per pet.

Guest favourite
A cozy sleeping area features a spacious bed centered against a wooden wall unit with built-in shelves. Soft bed linens in muted colors are arranged neatly, with decorative pillows adding a touch of style. Nightstands on either side hold elegant lamps that softly illuminate the space.
Apartment in Edgewood
4.95 out of 5 average rating, 510 reviews

Urban Garden Suite

Relax & Recharge in Westville’s Hidden Gem in New Haven. Unwind in this serene, beautiful, cozy, spotless garden apartment tucked inside a historic three-family home in charming Westville. The cozy, open-concept design blends modern upgrades with warm, thoughtful touches, creating the perfect balance of comfort and style.🌿 Enjoy peaceful surroundings, inviting details, and everything you need for a seamless stay. Your attentive (yet discreet) hostess ensures you’ll feel truly at home.

Superhost
A bright living area features two plush sofas, one in a muted beige and the other in a deep blue, positioned around a circular wooden coffee table. Light-colored curtains adorned with a coral pattern frame the windows, while shelves on the walls display decorative items.
Home in Bridgeport
4.95 out of 5 average rating, 132 reviews

Families|Charming |King Bed| Near SHU

Welcome to our updated and inviting nautical-themed residence. The home is located close to the University of Bridgeport, Sacred Hearth University and St Vincents Hospital. Enjoy the excitement of the ambiance around the fire pit in the private backyard and a grill for cooking, and the convenience of all of the amenities in the home. Guests can truly relax and make the most of their time in our tranquil setting. There is a dedicated workspace for remote workers and is family friendly.

Guest favourite
A welcoming living area features a comfortable couch and a textured ottoman, complemented by natural wood accents on the ceiling. Light fills the space from multiple windows, highlighting the hardwood floors and decorative stone wall that adds character to the room.
Cottage in Milford
4.94 out of 5 average rating, 365 reviews

Fall 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.

Top Guest favourite
A cozy living room is featured with a combination of a grey sofa and an orange couch. A decorative white coffee table rests on a patterned area rug, while a faux fireplace is accented by a round sunburst mirror and decorative items. Natural light enters through a nearby window.
Cottage in Milford
4.99 out of 5 average rating, 152 reviews

3BD Cottage | Walk 2 Beach and Tyde Wedding Venue

Walking distance from Walnut Beach and Tyde Wedding Venue! Stay at this cozy 3-bedroom, 1-bath beach cottage in the heart of Walnut Beach. Perfect for family vacations, wedding guests, or Yale visitors, our modern farmhouse-style home features a full kitchen, a private backyard with a fire pit, and peaceful coastal vibes. Walk to the sand, celebrate at Tyde, enjoy coffee on the porch, and end the day by the fire. Comfort, style, and location — all in one unforgettable stay!

Top Guest favourite
The bedroom features a queen size spindle bed with quality bedding, flanked by two nightstands with lamps. A dedicated work desk is equipped with a lamp and USB ports. Shelving adds storage, while a small seating area is present, illuminated by natural light from the windows.
Apartment in Fairfield
4.98 out of 5 average rating, 162 reviews

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.

Popular amenities for Bridgeport holiday rentals

When is the best time to visit Bridgeport?

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Avg. price$173 NZD$164 NZD$171 NZD$166 NZD$201 NZD$197 NZD$194 NZD$199 NZD$187 NZD$197 NZD$173 NZD$171 NZD
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Frequently Asked Questions

  • Are there apartment rentals with a dedicated workspace in Bridgeport?

    Yes! Work meets play with ease at over 60 apartment rentals in Bridgeport featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Where should I stay in Bridgeport?

    Make yourself at home in Bridgeport by choosing from our most frequently booked neighborhoods. We have over 400 vacation rentals in Seaside Park, over 490 vacation rentals in Steel Point, and over 400 vacation rentals in Black Rock.

  • How much does it cost to stay in apartment rentals in Bridgeport?

    Experience the best of Bridgeport with our apartment rentals, starting at about $10 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Bridgeport have a bbq area?

    Absolutely! We offer over 30 house rentals with a bbq area in Bridgeport. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Bridgeport have wifi?

    Absolutely! We offer over 100 apartment rentals with wifi in Bridgeport. Enjoy a tailored experience with all the comforts you desire.

  • Are there Bridgeport house rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 house rentals with pools in Bridgeport, available on Airbnb. Make a splash and soak up the sun in style!

  • What are the most popular amenities for House Rentals in Bridgeport?

    Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with a gym, over 30 homes with a bbq area, over 140 homes with air conditioning, over 160 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do house rentals in Bridgeport have a gym?

    Absolutely! We offer over 10 house rentals with a gym in Bridgeport. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly house rentals in Bridgeport?

    Bridgeport has more than 70 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do townhouse rentals in Bridgeport have air conditioning?

    Absolutely! We offer over 10 townhouse rentals with air conditioning in Bridgeport. Enjoy a tailored experience with all the comforts you desire.

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 $33 NZD per night before taxes and fees

  • Verified guest reviews

    Over 7,730 verified reviews to help you choose

  • Family-friendly holiday rentals

    140 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 80 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    200 properties have a dedicated workspace

  • Wi-Fi availability

    310 of Bridgeport holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Bridgeport rentals

  • 4.7 Average rating

    Bridgeport stays receive an average rating of 4.7 out of 5 from guests