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Freeport Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Freeport vacation rentals

A red cabin with a porch, surrounded by trees.

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, (40 reviews)
"Great place to stay"
United States
Mike G.
The price is CA $199
CA $241 total
includes taxes & fees
Oct 28 - Oct 29
Peace & Simplicity in a Little Red Cabin on the Farm
A wooden deck with potted plants, a hot tub, and a swimming pool.

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, (19 reviews)
"Great place to stay "
United States
Dulce C.
The price is CA $247
CA $424 total
includes taxes & fees
Oct 4 - Oct 5
Quite- relaxing country living with pool/hot tub and sauna!
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, (49 reviews)
"We have stayed here many times and always appreciate the thoughtfulness displayed by the hosts."
United States
Merry E.
The price is CA $183
CA $286 total
includes taxes & fees
Oct 3 - Oct 4
The Main St Place in charming Mount Carroll IL 1st floor
A spacious kitchen with wooden cabinets, a central island, and a dining area with a table and chairs.

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 CA $180
CA $356 total
includes taxes & fees
Oct 12 - Oct 13
Lookout Loft over the Monroe Square
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.

5. 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 CA $278
CA $390 total
includes taxes & fees
Oct 4 - Oct 5
MJ's Penthouse ,a piece of paradise on Monroe's historic square
A hammock in a grassy area with a lake and trees in the background.

6. Riverfront cabin on Rock River

Riverfront cabin on Rock River
Rockford
10.0 out of 10, Exceptional, (230 reviews)
"Great place to relax and fishing"
United States
Dmytro D.
The price is CA $249
CA $406 total
includes taxes & fees
Oct 11 - Oct 12
Riverfront cabin on Rock River
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.

7. Lake Cabin | Sauna · River · Game Room

Lake Cabin | Sauna · River · Game Room
Brodhead
9.8 out of 10, Exceptional, (13 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 CA $288
CA $1,041 total
includes taxes & fees
Oct 14 - Oct 15
Lake Cabin | Sauna · River · Game Room
A wooden deck with two blue Adirondack chairs and a small table, surrounded by a wooden railing with a view of a green landscape.

8. 8 Acres of Privacy Your Group Escape

8 Acres of Privacy Your Group Escape
Rockford
The price is CA $355
CA $562 total
includes taxes & fees
Oct 6 - Oct 7
8 Acres of Privacy Your Group Escape
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.
The price is CA $715
CA $1,125 total
includes taxes & fees
Oct 5 - Oct 6
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

Eugene Hotel

Eugene Hotel

10/10 Excellent
"The hotel has been nicely remodeled. Very friendly and quaint. The bed and pillows were soft,but comfortable."
Buffey 2-night trip
Posted 2 days ago
Eugene Hotel

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, cottages, cabins, villas... 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Freeport vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Freeport vacation rentals we have selected for you start as low as CA $241 per night. Entering your travel dates in the search wizard 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. 

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.