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Freeport Vacation Rentals

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Check prices for these dates

Tonight
Dec 26 - Dec 27
Tomorrow
Dec 27 - Dec 28
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Freeport vacation rentals

Interior
The Rustic Retreat: Elegant cabin with WiFi & AC in an enchanting location!

The Rustic Retreat: Elegant cabin with WiFi & AC in an enchanting location!

The Rustic Retreat: Elegant cabin with WiFi & AC in an enchanting location!
2.5 star property
Pearl City
10.0 out of 10, Exceptional, (3)
"Out of half a dozen or so cabin rentals, this one is the absolute best. It's clean, uncluttered, quiet, and huge! Water was hot, heater worked really well (it was a very cold week) and the kitchen worked well. Beds were comfy too. I can't say enough good things about this place!"
United States
Andrew R.
The price is ￥14,126
￥49,359 total
includes taxes & fees
Jan 12 - Jan 13, 2026
The Rustic Retreat: Elegant cabin with WiFi & AC in an enchanting location!
Interior
Peace & Simplicity in a Little Red Cabin on the Farm

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, (12)
"Quiet, clean and absolutely lovely cabin! "
United States
Holley B.
The price is ￥21,832
￥26,443 total
includes taxes & fees
Jan 9 - Jan 10, 2026
Peace & Simplicity in a Little Red Cabin on the Farm
Property grounds
Riverfront cabin on Rock River

Riverfront cabin on Rock River

Riverfront cabin on Rock River
Rockford
10.0 out of 10, Exceptional, (206)
" Good beds, well-equipped, great river views!"
United States
Stephen C.
The price is ￥27,290
￥44,456 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Riverfront cabin on Rock River
Living area
Lookout Loft over the Monroe Square

Lookout Loft over the Monroe Square

Lookout Loft over the Monroe Square
2.0 star property
Monroe
The price is ￥15,641
￥33,350 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Lookout Loft over the Monroe Square
Fridge, microwave, oven, stovetop
Beautiful two story, downtown home, one block from the Square,

Beautiful two story, downtown home, one block from the Square,

Beautiful two story, downtown home, one block from the Square,
Monroe
10.0 out of 10, Exceptional, (35)
"The property was wonderful and the hosts were great/accommodating. Wonderfully decorated, charming and location was perfect (as we were looking to be near the square for bars, restaurants and shopping).Highly recommend!"
United States
Frank B.
The price is ￥24,140
￥44,362 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Beautiful two story, downtown home, one block from the Square,
Interior
MJ's Penthouse ,a piece of paradise on Monroe's historic square

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, (102)
"Such a fun place to stay! We loved it!"
United States
Karen J.
The price is ￥30,408
￥41,322 total
includes taxes & fees
Jan 4 - Jan 5, 2026
MJ's Penthouse ,a piece of paradise on Monroe's historic square
Outdoor pool
Quite- relaxing country living with pool/hot tub and sauna!

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)
"Great place to stay "
United States
Dulce C.
The price is ￥29,667
￥50,140 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Quite- relaxing country living with pool/hot tub and sauna!
Smart TV
Insta-worthy Rock River cabin

Insta-worthy Rock River cabin

Insta-worthy Rock River cabin
Byron
10.0 out of 10, Exceptional, (7)
"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 ￥31,478
￥54,042 total
includes taxes & fees
Jan 4 - Jan 5, 2026
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
"Clean room, friendly staff "
Larry 2-night trip
Posted 6 days ago
Paddle Wheel Inn

Find out more about Freeport

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Look no further and take a look at our great range of rental properties in Freeport!

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?

Apartment in private home, sleeps 7 guest: Visitors give good reviews to this Freeport vacation home rental, which is located in the city center 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 the selection of games in this rental home to help you unwind.

What can I see and do in Freeport?

Cultural attractions include Stephenson County Historical Museum and Freeport Art 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 Silver Creek Museum.

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.