
Vacation rentals in Bridgeport
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Top-rated vacation rentals in Bridgeport
Guests agree: these stays are highly rated for location, cleanliness, and more.

Private Inn
Private(not shared) self check-in, clean, quiet, safe, and free off street parking on a cul de sac road. The suite is 600sq your own private bathroom, backyard, and number keypad for your convenience to enter/exit into the suite at will, there is high speed Wi-Fi, HD cable tv, Kcup machine, heat/ac (indoor fireplace) also a firepit outsde ,rubber track and tennis courts literally in the back yard. 5miles away from Yale/nh and 5mins to Griffen Hospital and major highways great local restaurants

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.

Water front studio apartment with fireplace.
This is a beautifully appointed studio apartment located off the patio level of a water front home. Guests enjoy a large private patio over looking gorgeous sweeping views of Long Island Sound. A private entrance and off street parking. The amazing views and amenities make this space the perfect romantic getaway! Close to I95 and Metro North railroad. Ten minutes to great dining in downtown Milford. A true waterfront oasis! Come and experience this beautiful retreat! You won't be disappointed!

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

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

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.

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 :).

The River Loft
Escape to The River Loft, a private riverfront retreat in Weston, CT. Built in 2015 by a visionary local architect, The River Loft open-air design seamlessly integrates the outdoors with the interior space. As you step inside this 750 sf small home, you'll be instantly captivated by the layout that makes it feel spacious. Sitting on over 2 acres of forested land with private river access. Book now for an unforgettable experience. For more images & videos visit insta @the.riverloft

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.

A Lovely Cottage in the Woods
Welcome to our cottage located just 1 hour north of NYC! It is nestled into 2.7 acres of beautiful gardens, mossy groves, and lovely woods. Nature abounds: The property abuts the 4000 acres of the Ward Pound Ridge Reservation. A trailhead begins right across the driveway. The cottage is equipped with a stone fireplace, spacious kitchen, living room area, table for dining and working, and a sleeping loft. During the summer, a private salt water pool is available.
Popular amenities for Bridgeport vacation rentals
Other great vacation rentals in Bridgeport

5 Minute Walk to Beach & Downtown Fairfield

Hermoso, limpio y tranquilo lugar para relajase

Charming Riverview Home*Firepit* Near Train & I-95

New & Stylish 2 King Bed Apartment w/ Grand Dining

Lavish retreat near downtown

New & Modern Studio Apartment in Fairfield

Cozy Studio in Bridgeport

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 | R1,777 ZAR | R1,692 ZAR | R1,760 ZAR | R1,709 ZAR | R2,068 ZAR | R2,034 ZAR | R1,999 ZAR | R2,051 ZAR | R1,931 ZAR | R2,034 ZAR | R1,777 ZAR | R1,760 ZAR |
| 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 pet-friendly house rentals in Bridgeport?
Four-legged friends are welcome in Bridgeport. Choose from more than 30 house rentals for guests traveling with pets.
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.
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 520 vacation rentals in Reservoir - Whiskey Hill, and over 380 vacation rentals in Black Rock.
Are there family-friendly apartment rentals in Bridgeport?
Bridgeport has more than 50 family-friendly apartment 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.
Do apartment rentals in Bridgeport have a bbq area?
Absolutely! We offer over 10 apartment 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 Apartment Rentals in Bridgeport?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 90 homes with air conditioning, over 10 homes with a bbq area, over 100 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there house rentals with a dedicated workspace in Bridgeport?
Yes! Work meets play with ease at over 100 house rentals in Bridgeport featuring dedicated workspaces. Stay connected and productive in your home away from home.
Quick stats about vacation rentals in Bridgeport

Total vacation rentals
Explore 300 vacation rentals in Bridgeport

Nightly prices starting at
Bridgeport vacation rentals start at R171 ZAR per night before taxes and fees

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

Family-friendly vacation rentals
130 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 80 rentals that welcome pets

Vacation rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
190 properties have a dedicated workspace

Wi-Fi availability
290 of Bridgeport vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool 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
- 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
- The Metropolitan Museum of Art
- Gilgo Beach
- Astoria Park
- Robert Moses State Park
- Thunder Ridge Ski Area
- Bronx Zoo
- Walnut Public Beach
- Shinnecock Hills Golf Club
- Bethpage State Park
- Rye Playland Beach
- Jones Beach State Park
- Cedar Beach
- TPC River Highlands




