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Freeport Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Freeport vacation 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, (19 reviews)
"Great place to stay "
United States
Dulce C.
$312 nightly
The price is $331
Oct 15 - Oct 16
Total with taxes and fees
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, (112 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
$248 nightly
The price is $272
Oct 18 - Oct 19
Total with taxes and fees
MJ's Penthouse ,a piece of paradise on Monroe's historic square
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.

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, (50 reviews)
"We have stayed here many times and always appreciate the thoughtfulness displayed by the hosts."
United States
Merry E.
$193 nightly
The price is $205
Oct 15 - Oct 16
Total with taxes and fees
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.

4. Lake Cabin | Sauna · River · Game Room

Lake Cabin | Sauna · River · Game Room
Brodhead
9.8 out of 10, Exceptional, (14 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.
$686 nightly
The price is $724
Oct 15 - Oct 16
Total with taxes and fees
Lake Cabin | Sauna · River · Game Room
A red cabin with a porch, surrounded by trees.

5. 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, (42 reviews)
"Great place to stay"
United States
Mike G.
$160 nightly
The price is $170
Oct 19 - Oct 20
Total with taxes and fees
Peace & Simplicity in a Little Red Cabin on the Farm
A spacious kitchen with wooden cabinets, a central island, and a dining area with a table and chairs.

6. 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.
$234 nightly
The price is $256
Nov 9 - Nov 10
Total with taxes and fees
Lookout Loft over the Monroe Square
A wooden deck with two blue Adirondack chairs and a small table, surrounded by a wooden railing with a view of a green landscape.

7. 8 Acres of Privacy Your Group Escape

8 Acres of Privacy Your Group Escape
Rockford
$336 nightly
The price is $375
Nov 3 - Nov 4
Total with taxes and fees
8 Acres of Privacy Your Group Escape
A hammock in a grassy area with a lake and trees in the background.

8. Riverfront cabin on Rock River

Riverfront cabin on Rock River
Rockford
10.0 out of 10, Exceptional, (231 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.
$297 nightly
The price is $315
Oct 15 - Oct 16
Total with taxes and fees
Riverfront cabin on Rock River
A spacious living room with a large window, a dining area with a wooden table, and a kitchen with a marble countertop.

9. 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.
$740 nightly
The price is $785
Oct 15 - Oct 16
Total with taxes and fees
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

Paddle Wheel Inn

Paddle Wheel Inn

10/10 Excellent
"Spacious clean room, loved the sliding glass door out to our own patio, beautiful view of the river and Chief Blackhawk statue. The only thing needed is a non slip bath mat the bottom of the tub is very slippery. The staff were friendly and helpful. Would definitely come stay again."
Colleen 2-night trip
Posted 14 hours ago
Paddle Wheel Inn

Find out more about Freeport

Everything you need to know about Freeport 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 Freeport 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 Freeport vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Freeport vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Freeport. 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 Freeport 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 $170 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 Freeport rentals

At Expedia, we put the best Freeport 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 Freeport 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 Freeport 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 Freeport. 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 Freeport?

Yes, we give you a choice of vacation rentals in Freeport close to Little Cubs Field, or you can select a secluded option if you're looking for extra privacy while you relax. 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 vacation rentals that Freeport has to offer?

Riverfront cabin on Rock River: Visitors like this Freeport vacation home rental. It is located on a river and has a patio, a private yard, and a barbecue grill 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 vacation rentals like in Freeport?

Vacation rentals are privately owned properties you can stay in for a short or long stay in Freeport. Vacation rentals offer extras such as patios, hot tubs, and fire pits so you'll have a home away from home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of privacy away from shared hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive option for a small group gathering.