Holiday rentals in Bridgeport

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Top-rated holiday rentals in Bridgeport

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
A studio-style layout features a spacious bed dressed in colorful stripes, accompanied by a cozy armchair and a small table. Natural light fills the room through large windows, and decorative elements include a painting above the bed and a sunburst mirror on the wall.
Loft in Newton
4.98 out of 5 average rating, 104 reviews

Meraki Loft

A peaceful atmosphere in a quaint small town, Meraki Loft is a place for you to be still and hear your own voice. This loft is situated on the north side of the town square in Newton, IL in one of Jasper County's oldest buildings. Guests are invited to enjoy our relaxing atmosphere, go for walk on the nearby Eagle Trails, visit a neighboring gym, take a class at the Dance Hall Studio, receive a healing touch massage, or visit one of our many natural resources. Most of all, live in the moment.

Top guest favourite
Home in Olney
4.98 out of 5 average rating, 93 reviews

Lakeside Lodge w/Private Beach

Nestled on the shores of Borah Lake, our 2-story lodge is the perfect escape for families and anglers. Enjoy a myriad of water adventures: swim, fish, or dock your boat right at your doorstep, or regular viewing of White Squirrels and other wildlife💗 As the sun sets, retreat into our cozy haven or gather around a crackling campfire. Embrace the essence of lake-life in a place where each moment is not just spent, but cherished. Ready for an unforgettable stay? Book your dream retreat today! 😍

Superhost
A spacious bedroom features a large bed with neutral linens and two pink pillows. A flat-screen television is mounted on the wall opposite the bed. Natural light filters through sheer curtains covering the window, while a full-length mirror stands beside the window.
Home in Lawrenceville
4.83 out of 5 average rating, 12 reviews

Home away from Home

Beautiful, classic rural location with both Cape cod and craftsman style features on 1 acre with amazing garden and trees including walnut,3 cherry trees, and blackberries. located only 7 miles from downtown Vincennes Indiana and 5 minutes from downtown Lawrenceville Walmart. Home has many features 2 bedrooms and a dedicated office space with ample closet space. 2 modern bathrooms, family room, large dinning room, a modern eat - in kitchen, Security cameras around the perimeter outside.

Guest favourite
The home’s entrance is illuminated by soft outdoor lights, highlighting a covered porch with two comfortable chairs. Steps lead up to the front door, surrounded by light snow on the ground, creating a serene evening ambiance.
Home in Robinson
4.95 out of 5 average rating, 107 reviews

The Relax Inn. Freshly remodeled 3 bed 2 bath home

This stylish freshly remodeled house is perfect for the weekend getaway or a long-term stay. The home offers plenty of room for the whole family as well as pets. There is a nicely shaded back yard with a swing set, playhouse and gas grill. The house provides all the necessary amenities and a few extras for a comfortable stay. The house is located close to the Robinson Refinery and offers plenty of parking. This property is designed for comfort for traveling workers and their families.

Guest favourite
An open dining area features a wooden table surrounded by black chairs. A lighted ceiling fan adds to the space, while a clock is mounted on the wall. The kitchen is visible, equipped with a white refrigerator and cabinetry, and a large window allows natural light to filter in.
Home in Olney
4.93 out of 5 average rating, 14 reviews

The Adams Street Suite

This quiet, cozy home is tucked into a peaceful neighborhood—perfect for relaxing after a long day of travel, work, or adventure. The Adam’s Street Suite offers a comfortable feel with thoughtful touches throughout, including a coffee bar to jumpstart your mornings. Whether you’re visiting for a night or a longer stay, you’ll find everything you need to feel at ease. Clean, stylish, and designed for comfort—this is the perfect spot to rest, recharge, and enjoy your stay.

Guest favourite
The exterior of a charming tiny home is depicted, featuring a light-colored facade with a welcoming front porch. Two chairs are positioned on the porch, and twinkling string lights above enhance the outdoor space. Surrounding trees provide a natural backdrop.
Tiny home in Olney
4.95 out of 5 average rating, 87 reviews

The Burkhaus

Welcome to The Burkhaus, your perfect getaway in our charming small town. This renovated tiny home offers a unique, intimate retreat. Nestled in our friendly community, you'll find a cozy loft bed with bamboo sheets and a memory foam mattress, ensuring a restful night's sleep. Relax on the porch, ideal for morning coffee or unwinding under twinkling patio lights. The Burkhaus isn't just a place to stay—it's a place to feel at home and experience genuine small-town charm.

Guest favourite
A welcoming entryway features two white plastic chairs positioned by a small, wooden shelf. A potted plant sits atop the shelf, while a doormat with the word 'Welcome' greets guests. The floor is adorned with a blue and white chevron pattern, enhancing the airy space.
Flat in Vincennes
4.8 out of 5 average rating, 46 reviews

1 Bedroom Apartment Unit 1

Private one bedroom one bathroom with large kitchen! Close to everything. Located 1 block from the library. 0.5 miles from Vincennes University. 0.9 miles to Good Sam. A hotel room with a full kitchen AND it’s cheaper. Fully equipped kitchen provides coffee pot, filters, paper towels, etc for easy use. Willing to accommodate pets for an additional fee of $25 for cleaning and count them as a guest ($10 per day). *Backyard is currently unavailable.

Guest favourite
A modern bathroom features a wooden vanity with a smooth countertop and multiple faucets. A large mirror reflects the space, while beige and grey tiles complement the decor. The shower area showcases a tiled wall with decorative accents, providing a clean and functional atmosphere.
Guest suite in Fairfield
4.83 out of 5 average rating, 235 reviews

Day of Rest

This place is in a private, residential neighborhood but only a few blocks from businesses, shopping and restaurants. There are two small parks for children to play at, nearby. There is plenty of parking for multiple vehicles or a commercial truck/trailer. Bright outdoor LED lighting provides a safe atmosphere. This property is attached to a small venue. The venue has a full kitchen area that can be rented for an additional fee.

Top guest favourite
The cabin's exterior is gently nestled among lush greenery, showcasing wood siding and a welcoming red front door. A paved pathway leads through manicured landscaping, with trees providing shade in the vicinity. The serene lake is visible behind the cabin, enhancing the natural setting.
Cabin in West Salem
4.99 out of 5 average rating, 142 reviews

Lake Cabin in the Woods

🌲Escape to peace and nature at Lake Cabin in the Woods! Unwind in your private hot tub, enjoy the shared pool, and soak up year-round tranquility surrounded by trees and wildlife. Located between I-70 and I-64, about 60 miles from Effingham, IL and Evansville, IN, our cozy cabin offers the perfect blend of seclusion and convenience—ideal for relaxing, recharging, and reconnecting with nature.

Top guest favourite
An open living space displays a rustic design with exposed wooden walls and a metal ceiling. A comfortable recliner is positioned near a modern kitchen featuring stainless steel appliances. A vintage-style coffee table and accent pieces enhance the lively atmosphere of the room.
Home in Olney
4.97 out of 5 average rating, 105 reviews

Chateau Monroe - Rustic feel / modern convenience

This 2 bedroom 1.5 bath home got a major facelift in 2020. It is located in a quiet neighborhood and has all the conveniences you could want. Hi-speed internet, washer & dryer, dishwasher, tankless water heater with endless hot water. 58" TV, even a record player. There are 2 bedrooms with a queen bed in each room. There is also a sectional that suits fine for a child or teen to crash on.

Guest favourite
A single-story white house is depicted, featuring a central door framed by two windows on either side. A mailbox is located beside the door, and a grassy area extends to the right. Leafless trees stand in the background, complementing the residential setting.
Flat in Robinson
4.98 out of 5 average rating, 40 reviews

Cozy retreat apartment

Kick back and relax in this calm, stylish, newly remodeled 1 bedroom/1 bath apartment. Located in the heart of Robinson, several blocks from the city park; you will love the peace and quiet of a relaxed neighborhood while enjoying easy access to the many restaurants and shops Robinson has to offer!

Top guest favourite
The guesthouse exterior is framed by lush greenery and colorful flower beds, featuring a rustic wooden facade. Large windows allow natural light into the interiors. A stone pathway leads to the entrance, enhancing the inviting atmosphere of the property surrounded by mature trees.
Cabin in Robinson
4.98 out of 5 average rating, 141 reviews

Rustic Guest House Cabin in a Secluded Setting

Let this guesthouse be your home away from home! Guests will enjoy the rustic feel of the private guesthouse located on 1 acre of land and surrounded by mature trees. Nearby in Robinson there are historic sites, hiking & lakes, golf, wineries and much more!

Popular amenities for Bridgeport holiday rentals

  1. Airbnb
  2. United States
  3. Illinois
  4. Lawrence County
  5. Bridgeport