
House holiday rentals in Bridgeport
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Top-rated house rentals in Bridgeport
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1956 House of the Year Award. Easy commute to NYC.
Architectural masterpiece, designed by famous architect Ulrich Franzen. House of the year awarded in 1956 by Architectural Record, featured in LIFE and House and Garden magazines. Taste the unique experience of modernist living, surrounded by nature yet walking distance to the beautiful town of Rye, the beach, natural parks and 45m by train to NYC. The house is filled with light,all the rooms have forest views,you feel inmersed in nature while enjoying the magical experience of modernist living!

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.

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!

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!

Fairfield Entire Upstairs Suite / 2Rms + 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

The Cozy Little Cottage
Charming guest apartment on our property on 1.5 acres in pastoral neighborhood, 7 minutes to Wilton center and 8 to Westport center. The cottage is a good size for 1-2 adults, can fit 3 people if one is a child. The unit is separate from our house, connected by a breezeway, above the garage. It is quaint and cozy. High end kitchen appliances include gas range, mini fridge, microwave and mini dishwasher. The bedroom has a queen bed. We have a twin air mattress for use in the living room.

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.

Peaceful Suburban Colonial w/New Kitchen.
Looking for a clean, cozy, secluded suburban escape that's still close to great shopping, Long Island Sound, and the two Fairfield Universities? Look no further than this newly renovated colonial on a quiet tree-lined street with no through traffic. A park and basketball are just at the end of the street. Trader Joes and other great shopping are a 2 minute drive away. Sacred Heart and Fairfield U are 5 minutes away. We're right across the street in case any of us forgot anything :).

HGTV reno! Fall Foliage, near New Haven, Firepit!
*Inquire now monthly discount Jan* *Brand New Major Renovation in 2023* • Fully renovated, designer beach house • Steps away from quaint downtown •1 block from water •Walk to beach, restaurants, coffee, ice cream, deli & convenience store, liquor and more... • Luxe, white, 100% cotton sheets & fluffy duvets •FULLY FENCED backyard with outdoor seating, BBQ grill, & fire pit .Easy drive to Sacred Heart, Fairfield, & Yale .STEPS to Tyde wedding venue .Fiber internet for fast speeds

Lakeview Estate - Chef's Kitchen - NYC Getaway
Stunning lake views from every angle! Gorgeous 3,200 square foot custom home with an open floor plan. Highlights include: * Chef's kitchen with Viking Range, Sub Zero Refrigerator, granite countertops & custom cabinets * Expansive 20x30 stone patio overlooking the lake with a fire-pit, speakers & outdoor lighting * 3 spacious bedrooms and 3 full bathrooms with double vanities, showers & separate bathtubs. * 5 SmartTVs including a 65" TV in the main living area

Top Rated Gem | Fire Pit | BBQ | FFU | Near Beach
Welcome to Fairfield Cottage, a cozy retreat that beautifully combines comfort and stylish design for you and your guests. With thoughtful decor and essential amenities, you'll feel right at home. Conveniently located just 90 minutes to NYC, you can easily visit attractions like the Norwalk Aquarium, Beardsley Zoo, and local farms. Unwind at nearby Jennings and Penfield beaches located just 3 miles away, or explore the charming village of Southport.

Cozy Colonial Style House in Beach Town
Charming home in calm New England neighborhood. Well connected: 20 mins to New Haven, 90 mins to New York, 2.5h to Boston. Colonial style with beautiful hardwood floors, lots of outside seating space on front and back porch. Back yard dining table and private driveway for 2-3 cars. A few minutes from Walnut Beach and Silver Sands State park as well as forest trails. Within walking distance from a brewery, restaurants, and a playground.
Popular amenities for Bridgeport house rentals
House rentals with a pool

Private Hudson Valley Country Retreat

Dream Home w/ Pool & Basketball Court on 3 Acres

Midcentury Modern ZenHouse Sculptor Studio

Spacious 4 bedroom, oasis with ocean views galore

Riverfront Cottage-Pool-Hot Tub-Fireplace 35m>NYC

Meeker Hill House - Country Escape w/ Heated Pool

Peaceful Light-Filled Guesthouse 1 Hour From NYC

Port Jefferson Convenient, Cozy and Chic!
Weekly house rentals

Bobby's Beach Bungalow

Newly Built Beach House Getaway

Adorable Beach House on LI Sound

❤️ Your Silvermine Hideaway, nestled in nature.

Cape on the Water

The Salty Porch

Lavish retreat near downtown

Cozy, updated single family in Fairfield County
Private house rentals

Westshore Luxury

Entire Home in Fairfield, beach & train ~5min

Westville Schoolhouse by Stephanie and Damian

Private 1-Bdrm Apt in West Haven

Serenity by Lakefront Cottage!

Fairfield’s Four bedroom Family Home

Hilltop Retreat- Lakefront with Dock

The Rose
When is the best time to visit Bridgeport?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $131 AUD | $125 AUD | $122 AUD | $122 AUD | $153 AUD | $154 AUD | $154 AUD | $137 AUD | $154 AUD | $153 AUD | $131 AUD | $131 AUD |
| 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 |
Quick stats about house rentals in Bridgeport

Total holiday rentals
Explore 160 holiday rentals in Bridgeport

Nightly prices starting at
Bridgeport holiday rentals start at $31 AUD per night before taxes and fees

Verified guest reviews
Over 3,050 verified reviews to help you choose

Family-friendly holiday rentals
70 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 30 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
100 properties have a dedicated workspace

Wi-Fi availability
160 of Bridgeport holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Bridgeport rentals

4.8 Average rating
Bridgeport stays are highly rated by guests—averaging 4.8 out of 5!
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- Columbia University
- Yale University
- Central Park Zoo
- Jones Beach
- Yankee Stadium
- Fairfield Beach
- Citi Field
- Southampton Beach
- Rye Beach
- Cooper's Beach, Southampton
- USTA Billie Jean King National Tennis Center
- Gilgo Beach
- The Metropolitan Museum of Art
- Robert Moses State Park
- Astoria Park
- Bronx Zoo
- Thunder Ridge Ski Area
- Walnut Public Beach
- Rowayton Community Beach
- Shinnecock Hills Golf Club
- Bethpage State Park
- Rye Playland Beach
- Cedar Beach
- Jones Beach State Park