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Bridgeport Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Bridgeport vacation rentals

A modern kitchen with wooden cabinets, a central island with stools, a built-in stove, and a window providing natural light.

1. Relaxing Small-Town Retreat in Lawrenceville

Relaxing Small-Town Retreat in Lawrenceville
Lawrenceville
10.0 out of 10, Exceptional, (18 reviews)
"We come to Lawranceville Illinois several times a year from Georgia and we always stay there!! We love it! Very comfortable and cozy!!!"
United States
Lori L.
$235 nightly
The price is $249
Oct 6 - Oct 7
Total with taxes and fees
Relaxing Small-Town Retreat in Lawrenceville
A modern kitchen with a microwave, stove, and sink.

2. ACE STAYS: Modern 1 BR apartment in Vincennes

ACE STAYS: Modern 1 BR apartment in Vincennes
Vincennes
$160 nightly
The price is $184
Oct 22 - Oct 23
Total with taxes and fees
ACE STAYS: Modern 1 BR apartment in Vincennes
A hallway with grey walls and a grey wooden floor.

3. Quaint 1BR with Kitchenette

Quaint 1BR with Kitchenette
Robinson
10.0 out of 10, Exceptional, (1 review)
$176 nightly
The price is $186
Oct 6 - Oct 7
Total with taxes and fees
Quaint 1BR with Kitchenette
A black door with a grid pattern, a white door frame, and a small sign above the door reading "103 West Walnut".

4. Cozy Loft Hideaway in Robinson

Cozy Loft Hideaway in Robinson
Robinson
10.0 out of 10, Exceptional, (3 reviews)
"Very pleasant stay. The loft was very clean and cozy as advertised."
United States
Mitchell M.
$192 nightly
The price is $203
Oct 10 - Oct 11
Total with taxes and fees
Cozy Loft Hideaway in Robinson
A hallway with a white door, a white table with a vase, and a light switch on the wall.

5. Ace Stays : Vincennes 1BR

Ace Stays : Vincennes 1BR
Vincennes
$195 nightly
The price is $224
Oct 14 - Oct 15
Total with taxes and fees
Ace Stays : Vincennes 1BR
A kitchen with wooden cabinets, a central island with two bar stools, a microwave, a refrigerator, and a window with blinds.

6. Enjoyable 3-bedroom house in charming Robinson

Enjoyable 3-bedroom house in charming Robinson
Robinson
9.4 out of 10, Exceptional, (3 reviews)
"Convenient, had a nice stay"
United States
Karen
$177 nightly
The price is $188
Oct 12 - Oct 13
Total with taxes and fees
Enjoyable 3-bedroom house in charming Robinson
A room with a wooden ceiling, a white door, a table with two chairs, and a small side table with a sign.

7. Tiny House

Tiny House
Olney
$140 nightly
The price is $148
Oct 7 - Oct 8
Total with taxes and fees
Tiny House
A bedroom with a bed, a TV, a dresser, and two doors.

8. 3 BR House Near Hershey/Marathon

3 BR House Near Hershey/Marathon
Robinson
$210 nightly
The price is $212
Oct 9 - Oct 10
Total with taxes and fees
3 BR House Near Hershey/Marathon
A door with two windows, each with horizontal blinds, and a keyhole in the center.

9. New listing! Private 3 bedroom 2 bath home with BEAUTIFUL sunroom!

New listing! Private 3 bedroom 2 bath home with BEAUTIFUL sunroom!
Olney
10.0 out of 10, Exceptional, (71 reviews)
"nice place."
United States
john m.
$186 nightly
The price is $197
Oct 6 - Oct 7
Total with taxes and fees
New listing! Private 3 bedroom 2 bath home with BEAUTIFUL sunroom!
A living room with a fireplace, leather sofas, and a clock on the wall.

10. Illinois Vacation Rental Home: Pets Welcome

Illinois Vacation Rental Home: Pets Welcome
Palestine
7.0 out of 10, Good, (2 reviews)
"Clean and comfortable. "
United States
Dori N.
Illinois Vacation Rental Home: Pets Welcome
A living room with a fireplace, leather sofas, and a clock on the wall.

11. Illinois Vacation Rental Home: Pets Welcome

Illinois Vacation Rental Home: Pets Welcome
3.0 star property
Palestine
10.0 out of 10, Exceptional, (1 review)
Illinois Vacation Rental Home: Pets Welcome
Interior

12. Studio with Queen Bed

Studio with Queen Bed
Robinson
10.0 out of 10, Exceptional, (1 review)
"Good value. Great location"
United States
Martin
$120 nightly
The price is $121
Oct 10 - Oct 11
Total with taxes and fees
Studio with Queen Bed
A street view at night with buildings, a car parked on the side, and a tree in the foreground.

13. The Robinson Roost

The Robinson Roost
Robinson
10.0 out of 10, Exceptional, (2 reviews)
"Wonderful property and great host. Great communication, clean, organized, and all necessary amenities. We will definitely be back!"
United States
Cara T.
$297 nightly
The price is $300
Oct 9 - Oct 10
Total with taxes and fees
The Robinson Roost
A modern kitchen with a central island, white cabinetry, and a view of the outside through large windows.

14. 2 Bedroom Apartment in the Heart of Robinson

2 Bedroom Apartment in the Heart of Robinson
Robinson
10.0 out of 10, Exceptional, (3 reviews)
"It was a perfect location, we got up and went to all the shops in the square, we will definitely be back "
United States
Betty D.
2 Bedroom Apartment in the Heart of Robinson
A compact kitchen with a refrigerator, stove, microwave, and dining table with chairs.

15. 3 Bed/1 Bath Close to Everything in Robinson

3 Bed/1 Bath Close to Everything in Robinson
Robinson
$228 nightly
The price is $229
Oct 11 - Oct 12
Total with taxes and fees
3 Bed/1 Bath Close to Everything in Robinson
A kitchen with wooden cabinets, a white refrigerator, and a chalkboard with a motivational quote.

16. Peaceful Meadows - Peaceful Meadows

Peaceful Meadows - Peaceful Meadows
Flat Rock
9.8 out of 10, Exceptional, (7 reviews)
"Great place to stay. Host was very welcoming."
United States
Patricia M.
$524 nightly
The price is $556
Oct 12 - Oct 13
Total with taxes and fees
Peaceful Meadows - Peaceful Meadows
A modern living room with a sectional sofa, a flat-screen TV, and a ceiling fan.

17. Comfortable 2BR on the Square

Comfortable 2BR on the Square
Robinson
10.0 out of 10, Exceptional, (4 reviews)
"Host communication was very good, apartment was as described. Stayed here for junior golf tournament."
United States
Brian D.
Comfortable 2BR on the Square
A spacious kitchen with modern appliances, a dining area with a glass-top table, and a ceiling fan.

18. Updated Robinson Vacation Rental w/ Fireplace!

Updated Robinson Vacation Rental w/ Fireplace!
Robinson
8.8 out of 10, Excellent, (3 reviews)
"Nice place! We watched eclipse on the trip. Had a great time. :DEvolve team answered our questions promptly."
United States
Minfei
$404 nightly
The price is $446
Oct 8 - Oct 9
Total with taxes and fees
Updated Robinson Vacation Rental w/ Fireplace!
A living room with a grey sofa, a black coffee table, a TV stand, and a patterned rug. There are two stools and a kitchen area visible in the background.

19. Spacious 3BR on the Square

Spacious 3BR on the Square
Robinson
2.0 out of 10, (1 review)
$235 nightly
The price is $248
Oct 13 - Oct 14
Total with taxes and fees
Spacious 3BR on the Square
A spacious kitchen with modern appliances, a dining area with a glass-top table, and a ceiling fan.

20. Updated Robinson Vacation Rental w/ Fireplace!

Updated Robinson Vacation Rental w/ Fireplace!
3.0 star property
Robinson
$394 nightly
The price is $437
Oct 8 - Oct 9
Total with taxes and fees
Updated Robinson Vacation Rental w/ Fireplace!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Bridgeport Hotel Reviews

Simply Home Inn & Suites

Simply Home Inn & Suites

8/10 Good
"Upgrades to the property are in progress and our room was excellent with the restoration done. My only real complaint is that there are signs that the grounds are being neglected. Brush and debris was seen in the parking area, the outside trash can was overfilled and looked as if it had not been emptied in weeks."
Joseph 3-night trip
Posted 6 hours ago
Simply Home Inn & Suites

Find out more about Bridgeport

Everything you need to know about Bridgeport vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Bridgeport vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Bridgeport vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Bridgeport vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Bridgeport. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Bridgeport in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $121 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Bridgeport rentals

At Expedia, we put the best Bridgeport vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Bridgeport rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Bridgeport vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Bridgeport. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Bridgeport?

Yes, there are vacation rentals close to top sights in Bridgeport, or you can select a more remote option if you want a relaxing place to stay.

What's the top vacation rental in Bridgeport?

The GreyStone House: Visitors like this Bridgeport vacation home rental. It is located in the city center and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of books.

What can I see and do in Bridgeport?

While exploring the area, visit family-friendly sights like Alvin Musgrove Park, or get outside and enjoy nature at Rogers Clark National Historical Park. In the larger area, you’ll find Red Hills State Park and Harrison Mansion.

What are vacation rentals like in Bridgeport?

Vacation rentals are privately owned properties you can stay in for a couple days or more in Bridgeport. Vacation rentals offer extras such as patios, hot tubs, and fire pits so you'll be comfy for your stay. If you're concerned about a sanitized environment, vacation rentals can offer a sense of seclusion away from public hotel elevators and busy lobbies while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great choice for families.