Freeport Holiday Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Freeport holiday rentals

A wooden deck with potted plants, a hot tub, and a swimming pool.

1. 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, (20 reviews)
"Great place to stay "
United States
Dulce C.
The price is HK$1,552
HK$2,351 total
includes taxes & fees
10 Nov - 11 Nov
Quite- relaxing country living with pool/hot tub and sauna!
A spacious living area with a wooden dining table, a sofa, and a hanging chair. There are large windows providing natural light and a view of the outside.

2. 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, (115 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 HK$1,529
HK$2,035 total
includes taxes & fees
10 Nov - 11 Nov
MJ's Penthouse ,a piece of paradise on Monroe's historic square
A spacious kitchen with wooden cabinets, a central island, and a dining area with a table and chairs.

3. 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 HK$1,354
HK$2,290 total
includes taxes & fees
10 Dec - 11 Dec
Lookout Loft over the Monroe Square
A red cabin with a porch, surrounded by trees.

4. 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, (46 reviews)
"Great place to stay"
United States
Mike G.
The price is HK$1,098
HK$1,263 total
includes taxes & fees
15 Nov - 16 Nov
Peace & Simplicity in a Little Red Cabin on the Farm
A kitchen with teal cabinets, a white countertop, and wooden flooring. There are hanging lights, a coffee maker, and various kitchen items on the shelves.

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

The Main St Place in charming Mount Carroll IL 1st floor
Mount Carroll
10.0 out of 10, Exceptional, (53 reviews)
"Great property, excellent hosts and charming decor. Quiet street and walking distance to shops and dining. This was our second stay there and we will definitely return!"
United States
Barbara B.
The price is HK$1,011
HK$1,512 total
includes taxes & fees
11 Nov - 12 Nov
The Main St Place in charming Mount Carroll IL 1st floor
A large, two-story log cabin with a stone chimney, a front porch with outdoor seating, and a snow-covered yard leading to a fire pit.

6. Lake Cabin | Sauna · River · Game Room

Lake Cabin | Sauna · River · Game Room
Brodhead
9.8 out of 10, Exceptional, (15 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 HK$1,806
HK$5,786 total
includes taxes & fees
18 Nov - 19 Nov
Lake Cabin | Sauna · River · Game Room
A hammock in a grassy area with a lake and trees in the background.

7. Cabin by the Rock River

Cabin by the Rock River
Rockford
10.0 out of 10, Exceptional, (233 reviews)
"Very Nice, Host was very helpful in all aspects. Great fishing and very relaxing Place was very clean and well organized and furnished. Would definitely stay here again."
United States
Dan L.
The price is HK$1,568
HK$2,351 total
includes taxes & fees
10 Nov - 11 Nov
Cabin by the Rock River
A castle-like structure with multiple towers and a central archway, surrounded by a paved area and trees.

8. Quiet Charm Near Recreation Park

Quiet Charm Near Recreation Park
Monroe
The price is HK$882
HK$1,927 total
includes taxes & fees
22 Nov - 23 Nov
Quiet Charm Near Recreation Park
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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Find out more about Freeport

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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 Lincoln-Douglas Debate Square and Oscar Taylor Home.

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.