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Freeport Holiday Rentals

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Our top choices for Freeport holiday rentals

1. Peace & Simplicity in a Little Red Cabin on the Farm

Peace & Simplicity in a Little Red Cabin on the Farm
Lena
10.0 out of 10, Exceptional, (39 reviews)
"Great place to stay"
United States
Mike G.
The price is NZ$296
includes taxes & fees
24 Sept - 25 Sept
Peace & Simplicity in a Little Red Cabin on the Farm

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

Quite- relaxing country living with pool/hot tub and sauna!
Pecatonica
10.0 out of 10, Exceptional, (18 reviews)
"Great place to stay "
United States
Dulce C.
The price is NZ$525
includes taxes & fees
21 Sept - 22 Sept
Quite- relaxing country living with pool/hot tub and sauna!

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

The Main St Place in charming Mount Carroll IL 1st floor
Mount Carroll
9.8 out of 10, Exceptional, (49 reviews)
"We have stayed here many times and always appreciate the thoughtfulness displayed by the hosts."
United States
Merry E.
The price is NZ$352
includes taxes & fees
21 Sept - 22 Sept
The Main St Place in charming Mount Carroll IL 1st floor

4. Lookout Loft over the Monroe Square

Lookout Loft over the Monroe Square
Monroe
10.0 out of 10, Exceptional, (4 reviews)
"Great property and host! Would stay there again."
United States
Ann S.
The price is NZ$384
includes taxes & fees
22 Sept - 23 Sept
Lookout Loft over the Monroe Square

5. Riverfront cabin on Rock River

Riverfront cabin on Rock River
Rockford
10.0 out of 10, Exceptional, (229 reviews)
"Great place to relax and fishing"
United States
Dmytro D.
The price is NZ$496
includes taxes & fees
27 Sept - 28 Sept
Riverfront cabin on Rock River

6. MJ's Penthouse ,a piece of paradise on Monroe's historic square

MJ's Penthouse ,a piece of paradise on Monroe's historic square
Monroe
10.0 out of 10, Exceptional, (111 reviews)
"The Penthouse is beautiful and the location is unbeatable! We had a wonderful stay and can't wait to come back."
United States
Andie
The price is NZ$471
includes taxes & fees
21 Sept - 22 Sept
MJ's Penthouse ,a piece of paradise on Monroe's historic square

7. Cozy 1-bedroom, fully renovated apartment in downtown Monroe

Cozy 1-bedroom, fully renovated apartment in downtown Monroe
Monroe
The price is NZ$383
includes taxes & fees
21 Oct - 22 Oct
Cozy 1-bedroom, fully renovated apartment in downtown Monroe

8. Lake Cabin | Sauna · River · Game Room

Lake Cabin | Sauna · River · Game Room
Brodhead
9.8 out of 10, Exceptional, (12 reviews)
"We love this property on the Sugar River. Very spacious, rustic but with all the modern amenities. Beautiful view of the water and lots of wildlife in area. "
United States
Lisa and Peter R.
The price is NZ$1,264
includes taxes & fees
18 Oct - 19 Oct
Lake Cabin | Sauna · River · Game Room

9. 8 Acres of Privacy Your Group Escape

8 Acres of Privacy Your Group Escape
Rockford
The price is NZ$573
includes taxes & fees
22 Sept - 23 Sept
8 Acres of Privacy Your Group Escape

10. Insta-worthy Rock River cabin

Insta-worthy Rock River cabin
Byron
10.0 out of 10, Exceptional, (10 reviews)
"Our check in was smooth, and it's a beautiful home with everything we needed for our stay."
United States
Beth G.
The price is NZ$1,347
includes taxes & fees
21 Sept - 22 Sept
Insta-worthy Rock River cabin
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 Freeport Hotel Reviews

Find out more about Freeport

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Freeport holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Freeport. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Freeport. Seeing all the best attractions is bound to make you fall in love with Freeport. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Freeport short-term rentals, that won’t be hard to do.

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?

Riverfront cabin on Rock River: This holiday home rental outside of Freeport is located on a river, and has a patio, a private garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

What can I see and do in Freeport?

Cultural attractions include Winneshiek Playhouse and Stephenson County Historical Museum, 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 Park Hills Golf Course.

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.