Freeport Vacation Rentals

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Vacation Rentals in Freeport

Duplex overlooking Rock River

Byron IL

Located in Byron, this vacation home is on a river, within a 10-minute drive of Stillman's Defeat Memorial Site and Wayside Park.

Kitchen

Washer

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

Monroe WI

$242 nightly

$265 total

Jan 5 - Jan 6, 2026

Total with taxes and fees

With a stay at this vacation home, you'll be centrally located in Monroe, just a 5-minute walk from Monroe Arts Center and 6 minutes by foot from Minhas Craft Brewery.

Kitchen

Washer

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

Monroe WI

$274 nightly

$300 total

Dec 7 - Dec 8

Total with taxes and fees

With a stay at this vacation home in Monroe, you'll be within a 10-minute walk of Monroe Arts Center and Minhas Craft Brewery.

Kitchen

Washer

2 Bedroom Cul De Sac Cottage in Town

Oregon IL

A stay at this vacation home places you in the heart of Oregon, within a 15-minute walk of Village Way Dog Park and Conover Square Mall.

Kitchen

Washer

Riverfront cabin on Rock River

Rockford IL

Located in Rockford, this vacation home is on the waterfront, within a 5-minute drive of Barnstormer Distillery and Wayside Park.

Kitchen

Washer

Whispering Woods Estate - Relax, recharge, connect

Rockton IL

This vacation home is 4.4 mi (7 km) from Village Green Park and 4.5 mi (7.3 km) from Settler's Park.

Kitchen

Washer

KC HOUSE Cozy Country Home. Enjoy the country life!

Rock City IL

With a stay at this vacation home in Rock City, you'll be 10.8 mi (17.3 km) from Sugar River Raceway and 14.8 mi (23.8 km) from Minhas Craft Brewery.

Hot Tub

Kitchen

Winnebago Spacious Home♥ Beautiful Kitchen LG Yard!!

Winnebago Township IL

With a stay at this vacation home in Winnebago, you'll be within a 5-minute drive of Winnebago Public Library and Winnebago Village Hall.

Kitchen

Washer

Family Friendly Modern Farmhouse 42 Private Acres

Elizabeth IL

When you stay at this vacation home in Elizabeth, you'll be on the waterfront and 10 minutes by car from Massbach Ridge Winery.

Kitchen

Washer

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

Mount Carroll IL

With a stay at this vacation home in Mount Carroll, you'll be 10.5 mi (16.9 km) from Bowen Park and 10.9 mi (17.5 km) from Savanna Train Car Museum.

Kitchen

Washer

Apartment in private home, sleeps 7 guest

Freeport IL

A stay at this vacation home places you in the heart of Freeport, a 5-minute drive from Freeport Art Museum and 5 minutes from Winneshiek Playhouse.

Kitchen

Washer

2br updated private entrance upstairs

Rockford IL

Located in Rockford, this vacation home is within a 5-minute drive of Ingersoll Memorial Park and Henrietta Park.

Washer

Dryer

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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.