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Freeport Holiday Rentals

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Holiday Rentals in Freeport

Entire lower level in a private home with walkout fenced yard.

9.4 out of 10, Exceptional, (8)
"Quiet location."
Entire lower level in a private home with walkout fenced yard.

Apartment in private home, sleeps 7 guest

10.0 out of 10, Exceptional, (4)
"Warm and spacious. Great hosts. We had a party of 5 and were very comfortable. There is a warm feel to the decor and everything was top notch!"
Apartment in private home, sleeps 7 guest

Riverfront cabin on Rock River

10.0 out of 10, Exceptional, (172)
"The access to the river was what drew us to stay I would have liked to be able to get the kayak in the water ( weather didnā€™t cooperate). "
Riverfront cabin on Rock River

KC HOUSE Cozy Country Home. Enjoy the country life!

10.0 out of 10, Exceptional, (8)
"The house and property are amazing. There are three levels of comfortable and beautiful living space, perfect for our large group. We had everything we needed. The host was super nice and accommodating.We had such a wonderfully relaxing stay. "
KC HOUSE Cozy Country Home. Enjoy the country life!

MJ's Penthouse ( a piece of paradise on Monroe's historic square)<br>

10.0 out of 10, Exceptional, (82)
"Cannot speak highly enough about this property. A hidden gem in Monroe! Such a relaxing and well designed place. Stayed for 2 nights this time and looking forward to my next visit."
The price is AU$413
includes taxes & fees
24 Nov - 25 Nov
MJ's Penthouse ( a piece of paradise on Monroe's historic square)<br>

Quite- relaxing country living with pool/hot tub and sauna!

10.0 out of 10, Exceptional, (16)
"we enjoyed our stay at this property. The hosts were attentive while still respecting our privacy and obviously wanted to be sure we had a good experience. The space was as described and the pool was terrific. We enjoyed being in a smaller town where we could see stars at night but close enough to Rockford with plenty of things to do. "
Quite- relaxing country living with pool/hot tub and sauna!

2br updated private entrance upstairs

The price is AU$266
includes taxes & fees
24 Nov - 25 Nov
2br updated private entrance upstairs

Pet-Friendly Mount Carroll Home w/ Fenced-In Yard!

8.4 out of 10, Very good, (5)
"Met our needs, "
Pet-Friendly Mount Carroll Home w/ Fenced-In Yard!

Unique Victorian Cottage Close to Town

10.0 out of 10, Exceptional, (13)
"This property is very nice. All the comforts of home. Very clean and love all the memorabilia it has. Highly recommend . "
Unique Victorian Cottage Close to Town

Historic Country Farmhouse for ANY Season!

10.0 out of 10, Exceptional, (40)
"Susan was amazing. The property was beautiful, super clean and had every needed and wanted. It was super relaxing!comfortable and roomy. "
Historic Country Farmhouse for ANY Season!

Family Friendly Modern Farmhouse 42 Private Acres

10.0 out of 10, Exceptional, (7)
"This was the most relaxing, beautiful VRBO we have ever stayed at. The land was gorgeous, sunrise and sunsets will bring tears to your eyes and refresh your soul. The owners Matt and Amanda make you feel like family and have thought of every single one of your needs, including, but not limited too, the best tp. We can't wait to return!! "
Family Friendly Modern Farmhouse 42 Private Acres

Duplex overlooking Rock River

10.0 out of 10, Exceptional, (21)
"We loved the view of Rock River. Being able to walk to many options for dining was great. Would definitely stay here again on future visits to Byron. Extremely clean!"
Duplex overlooking Rock River

2 Bedroom Cul De Sac Cottage in Town

10.0 out of 10, Exceptional, (28)
"clean and just what I needed."
2 Bedroom Cul De Sac Cottage in Town

Beautiful downtown home, one block from the Square,

10.0 out of 10, Exceptional, (23)
"Excellent house downtown Monroe. Awesome owners, who are great communicators."
Beautiful downtown home, one block from the Square,

The Main St Place in charming Mount Carroll IL 1st floor

9.8 out of 10, Exceptional, (30)
"Clean and convenient. Responsive hosts."
The Main St Place in charming Mount Carroll IL 1st floor

Waterfront Sugar River Cabin w/ Dock & Game Room!

9.6 out of 10, Exceptional, (5)
"This Cabin is the perfect weekend getaway; secluded but only a short drive from Madison. "
Waterfront Sugar River Cabin w/ Dock & Game Room!

Private Studio whole unit

Private Studio whole unit

A Breath of fresh Country Air with hot tub.

A Breath of fresh Country Air with hot tub.

Winnebago Spacious Homeā™„ Beautiful Kitchen LG Yard!!

10.0 out of 10, Exceptional, (19)
"House was great! Plenty of room with a beautiful kitchen. The deck was spacious with plenty of chairs but it could use a little TLC."
Winnebago Spacious Homeā™„ Beautiful Kitchen LG Yard!!

The Main St Place in charming Mount Carroll IL 2nd floor

10.0 out of 10, Exceptional, (3)
"The town is charming, historic, beautiful as is the house. We met a kind and generous neighbor."
The Main St Place in charming Mount Carroll IL 2nd floor
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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Other types of properties in Freeport you may be interested in

Country Inn & Suites by Radisson, Freeport, IL

2.5 star property
9.0 out of 10, Wonderful, (737)
"Only issue was pool closure on Saturday i understand the pump shut down so closing down at some point necessary but seeing as no was in the pool until early saturday evening allowing a few hours of swimmimg would not be a health alert "
The price is AU$176
includes taxes & fees
19 Dec - 20 Dec
Country Inn & Suites by Radisson, Freeport, IL

Baymont by Wyndham Freeport

2.5 star property
8.0 out of 10, Very good, (597)
"Great value. Nice breakfast. Secure. Helpful with our needs. Comfortable beds. Room condition was very good."
The price is AU$132
includes taxes & fees
22 Dec - 23 Dec
Baymont by Wyndham Freeport

Super 8 by Wyndham Freeport

2.0 star property
6.6 out of 10, (294)
"The Jacuzzi "
The price is AU$119
includes taxes & fees
1 Dec - 2 Dec
Super 8 by Wyndham Freeport
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Can I find holiday rentals in Freeport?

Yes, there are holiday rentals in Freeport close to Little Cubs Field, or you can select a more secluded option if you're looking for a relaxing stay. Freeport is known for its wineries and riverfront. Make sure you have time to check out the forests while you're in the area.

What are some of the best holiday rentals that Freeport has to offer?

Apartment in private home, sleeps 7 guest: This highly rated holiday home rental in Freeport is located in the city centre, and has a fireplace, a garden and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in Freeport?

Choose from 3 Expedia holiday rentals in Freeport for a memorable holiday.

What can I see and do in Freeport?

Cultural attractions include Freeport Art Museum and Winneshiek Playhouse, whereas Krape Park and Jane Addams Recreation Trail are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Little Cubs Field and Krape Park Carousel.

What are holiday rentals like in Freeport?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Freeport. Holiday rentals offer extras such as kitchens and laundry facilities so you'll have a home away from home. If you're concerned about a clean environment, a holiday rental can provide a sense of seclusion away from shared hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for family trips.