Holiday rentals near Bridgeport Downtown South Historic District
We found 324 holiday rentals — enter your dates for availability
If you'd like to stay close to Bridgeport Downtown South Historic District, take a look at holiday rentals to choose your home away from home. Whether you’re staying in a holiday home with your children and pets or just with friends, you'll have the best amenities for spending time at your home away from home, which might include Wi-Fi and a pool. At the end of the day, you'll be able to choose a property to rent to meet everyone's needs, including accessible or non-smoking choices.
Holiday rentals with weekly discounts - Bridgeport Downtown South Historic District
Showing deals for:21 Nov - 28 Nov
Image gallery for Renovated Milford Beach home by Charles Island/Silver Sands Pk
10 out of 10 rating
Exceptional
(6 reviews)
Renovated Milford Beach home by Charles Island/Silver Sands Pk
Milford, CT
8% off
Price is NZ$4,229
NZ$604 nightly
Includes taxes & fees
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Bridgeport Downtown South Historic District
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DUNE Fairfield Beach
Sleeps 2 · 1 bedroom
9.0 out of 10
wonderful
(65 reviews)
Top rated rentals - Bridgeport Downtown South Historic District
In town to check out Fairfield University
10 out of 10
exceptional
(6 reviews)
We were looking to book a shorter week in Fairfield to check out the university. This property allowed a shorter stay, which was extremely convenient for us. The location was a short drive to the university and within walking distance to the beach. The house itself was absolutely gorgeous. All levels were tastefully decorated, the house was clean, well lit, and included all modern amenities. The hosts were very attentive to our needs and responded in a timely manner. I would not hesitate to stay here again. One of the most beautiful properties I’ve ever stayed at near the beach.
Coleen C.
Stayed Jul 2025
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value