Holiday rentals in Bridgeport

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Top-rated holiday rentals in Bridgeport

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Guest favourite

Home in Fairfield

4.9 out of 5 average rating, 109 reviews

Fairfield 2nd Fl–2 Rms | Exclusive Entry & Parking

ENTIRE 2nd FL for up to 2️⃣ adult guests ONLY 2️⃣ Rooms➕Skylit Full Bath Exclusive Driveway Parking spots➕Private Main Entrance, separate from full-time renters on 1st FL using back entries 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

Top guest favourite

Guest suite in Fairfield

4.94 out of 5 average rating, 159 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.

Superhost

Home in Bridgeport

4.77 out of 5 average rating, 135 reviews

Golden Colonial Home

Your family will be close to everything when you stay at this centrally-located place. We are minutes away from Seaside Park Beach, Jennings Beach and Saint Mary’s by the Sea. You can make your way to any of our local fishing piers for the best fishing experience in the NorthEast. Our Downtown area is 5 minute drive and it’s full of night life and restaurants. We also have local farms near by great picking (strawberry, raspberry, apple, pumpkin) depending on the season. Beautiful trails views

Superhost

Flat in Bridgeport

5 out of 5 average rating, 4 reviews

Stylish 2King Bed Family Apartment w/no stairs req

🌟 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!

Superhost

Flat in Bridgeport

5 out of 5 average rating, 4 reviews

Lux Modern Loft ,Ricport Studio 1 Peaceful Stay

Downtown Bridgeport 1/1 stay experience. Minutes from Train station, Port Jeff Ferry, Amphitheater, Arena, Beach, Restaurants, Bars, Comedy Club, and much more. This is the perfect commuters dream. If you lived in a city or visited one, you’ll other stand why we offer air plugs, it can be loud at times outside. But in doors, you’ll feel the peace provided by its design including LIVE plants and aesthetics. You may want to stay longer. Enjoy your stay!

Guest favourite

Home in Fairfield

4.96 out of 5 average rating, 150 reviews

Top Rated Gem | Fire Pit | Near Beach, FFU & SHU

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.

Top guest favourite

Apartment in Stratford

5 out of 5 average rating, 26 reviews

Comfortable apartment near all communal facilities

I have an apartment located in an excellent quiet area with easy access. It is furnished and is very close to different areas such as supermarkets, restaurants, hospitals and universities. It also has 100% filtered water to drink. Something very important is that NO type of drugs are accepted, NO Viper or electronic cigarettes or Hookah are NOT accepted on this property. If we find odors or drug residues, they will be reported and fined.

Top guest favourite

Flat in Fairfield

4.98 out of 5 average rating, 130 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.

Guest favourite

Home in Bridgeport

4.9 out of 5 average rating, 50 reviews

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 . ( 1 Queen bed, 1 Sofa bed)

Guest favourite

Flat in Bridgeport

4.97 out of 5 average rating, 63 reviews

Beautiful, clean and quiet place to relax

The whole group will enjoy easy access to everything from this centrally located place. Close to everything strong wifi 2 blocks from the hospital centralized air and AC in each bedroom one parking spot on a dead end street in a quiet neighborhood safe and relaxing.

Holiday rentals for every style

Get the amount of space that is right for you

Houses

A space that's all yours, with room for everyone

Cabins

Kick off your hiking boots at these rustic lodgings

Flats

Convenient locations with everyday essentials

Popular amenities for Bridgeport holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Bridgeport

Guest favourite

Private room in Fairfield

4.92 out of 5 average rating, 66 reviews

Fairfield 2bedroom Suite w Private Entry & Parking

LianeRating, 5 stars1 month ago

This place is perfect for those looking for a welcoming place to sleep after engaging in activities in the area. The bedrooms are sizable and attractive, and the hosts are very friendly and responsive. While exactly as depicted in the photos, this place is hard to envision before arriving. One enters the main entrance of the house straight to a steep, dedicated, and private stairway at the top of which are two self-contained bedrooms, one on each side, with a bathroom in the hallway between them. In addition to the bed in each bedroom, one bedroom includes a desk, couch, dresser, microwave, coffee maker, and very small refrigerator, and the other includes a TV, two comfortable chairs, vanity table, mirror and closet.

Superhost

Private room in Stratford

4.91 out of 5 average rating, 11 reviews

Standard Room - Stratford CT

JacobRating, 5 stars7 months ago

Really nice place, everything about my stay with Alessandro went really smoothly!

Guest favourite

Private room in Stratford

4.94 out of 5 average rating, 32 reviews

Elegant & Cozy Sunlit Room

KathleenRating, 5 stars2 weeks ago

Great place with good lighting in the bedroom! Host was very kind and proactive.

Guest favourite

Private room in Bridgeport

5 out of 5 average rating, 13 reviews

Bright Room in the Lake House!

LuisRating, 5 stars3 weeks ago

Mara was a great host, we felt very welcome in her home. We would love to come back the next time we’re in the area.

Guest favourite

Private room in Hamden

4.98 out of 5 average rating, 93 reviews

Budget meets Boho-Chic!

DanielRating, 5 stars1 week ago

Fantastic hosts, very welcoming and accommodating. Room was very comfortable and clean. I appreciated the well stocked shower. Guestbook had lots of good local dining and activity recommendations. Would definitely return next time I stay in the New Haven area.

Guest favourite