
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.

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.

Lovely water front lower-level loft, free parking
This unique centrally located water front loft is located on the second Gulf Pond 1.5 miles from historic Milford center buzzing with water front restaurants and downtown shopping. This one bedroom, one bath, has a private entrance and free off street parking. Outdoor patio & grill with kitchenette, enjoy a waterfront view throughout the 400 sq ft space. Close to I-95, the Merrit Parkway, and Milford train station. Explore 17 miles of beaches in this New England town by bike, kayak, or foot.

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

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

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.

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.

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 :).

Fall Sale! CozyCottage/WalktoBeach/Pet-friendly
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.

Cozy Condo in Fairfield with Parking and Laundry!
Come stay in our clean and cozy condo located close to Fairfield University, great restaurants, local grocery stores, appliance centers, and other essential shops. Also includes: - Free Wi-Fi - Washer and dryer - Keurig with K-cups - Full kitchen with essentials - Smart Roku TVs with apps (Netflix, Hulu, etc.) - Fenced in/gated backyard - Outdoor patio set and grill - Free parking (4 car max) - Central heating and AC Perfect for those that need a temporary space!

Guest suite with private enter
Private room with private enter and bathroom attached dedicated work space and privat parking. On a 1.5 acres property. With fast internet. Located 5 minutes of walking distance from ASML office park, 5 minutes drive from Norwalk corporate park, 9 minutes drive from Wilton Downtown and 15 min drive from Norwalk train station. Close to a lot of restaurants, coffee shops, stores and parks. The owners live in other part of the house. Family owns cats.

Wintergreen Gardens Suite @ William Becroft House
LGBTQ friendly. Our 1915 Arts & Crafts bungalow's spacious in-law suite offers driveway parking, private entrance, sunroom, king bedroom, en-suite bath, kitchenette w/fridge, micro, coffee maker, toaster. Relax in bed with 40" HDTV with Amazon Prime, HBO Max, Netflix, premium cable. Enjoy private gardens to sun, read a book or cup of coffee. Short drive to 4 Vineyards, Theater and the train station. I am not responsible for wifi.

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
Other great holiday rentals in Bridgeport

Cozy bedroom near the beach.

Stylish 3BR Escape with Private Office by LI Ferry

Hermoso, limpio y tranquilo lugar para relajase

New & Stylish 2 King Bed Apartment w/ Grand Dining

LOVELY WELL APPOINTED ROOM - IN FAIRFIELD

New & Modern Studio Apartment in Fairfield

Cozy Private Suite Near Train to NYC

Cozy 1 Bd Private Entrance In-law Suite & Hot Tub
When is the best time to visit Bridgeport?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $181 NZD | $172 NZD | $179 NZD | $174 NZD | $210 NZD | $207 NZD | $203 NZD | $208 NZD | $196 NZD | $207 NZD | $181 NZD | $179 NZD |
| 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
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 380 vacation rentals in Seaside Park, over 470 vacation rentals in Steel Point, and over 380 vacation rentals in Black Rock.
How much does it cost to stay in townhouse rentals in Bridgeport?
Experience the best of Bridgeport with our townhouse rentals, starting at about $40 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 20 house rentals with a bbq area in Bridgeport. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Bridgeport have wifi?
Absolutely! We offer over 160 house 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 140 homes with air conditioning, over 20 homes with a bbq area, over 10 homes with a gym, 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 apartment rentals in Bridgeport have air conditioning?
Absolutely! We offer over 90 apartment 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 300 holiday rentals in Bridgeport

Nightly prices starting at
Bridgeport holiday rentals start at $17 NZD per night before taxes and fees

Verified guest reviews
Over 6,910 verified reviews to help you choose

Family-friendly holiday rentals
130 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
190 properties have a dedicated workspace

Wi-Fi availability
290 of Bridgeport holiday rentals include Wi-Fi 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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- Columbia University
- Central Park Zoo
- Yale University
- Jones Beach
- Yankee Stadium
- Citi Field
- Fairfield Beach
- Southampton Beach
- Rye Beach
- Cooper's Beach, Southampton
- USTA Billie Jean King National Tennis Center
- The Metropolitan Museum of Art
- Astoria Park
- Gilgo Beach
- Thunder Ridge Ski Area
- Robert Moses State Park Beach
- Bronx Zoo
- Rowayton Community Beach
- Walnut Public Beach
- Shinnecock Hills Golf Club
- Bethpage State Park
- Rye Playland Beach
- Cedar Beach
- TPC River Highlands




