Photo by Tina Techsavvymum

Freeport Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Oct 1 - Oct 2
Tomorrow
Oct 2 - Oct 3
This weekend
Oct 3 - Oct 5
Next weekend
Oct 10 - Oct 12

Vacation Rentals in Freeport

Apartment in private home, sleeps 7 guest
Exterior

Apartment in private home, sleeps 7 guest

10.0 out of 10, Exceptional, (6)
"Great experience! Hosts are great people. Would stay again if in the area. "
Apartment in private home, sleeps 7 guest
Riverfront cabin on Rock River
Property grounds

Riverfront cabin on Rock River

10.0 out of 10, Exceptional, (197)
"We had a great stay! Nice property with peaceful surroundings and everything you need. Would 100% stay again. "
The price is ￥25,727
￥41,598 total
includes taxes & fees
Oct 22 - Oct 23
Riverfront cabin on Rock River
Whispering Woods Estate - Relax, recharge, connect
Property grounds

Whispering Woods Estate - Relax, recharge, connect

10.0 out of 10, Exceptional, (1)
"This property exceeded our expectations. Communication with owners was perfect. Kitchen was well stocked with all our cooking needs. Bed very comfortable. Enjoyed the deck and grill. Large property for walking our dogs. We recommend this property and hope it is available the next time we are in the area. "
Whispering Woods Estate - Relax, recharge, connect
Peace & Simplicity in a Little Red Cabin on the Farm
Interior

Peace & Simplicity in a Little Red Cabin on the Farm

10.0 out of 10, Exceptional, (8)
The price is ￥17,347
￥21,502 total
includes taxes & fees
Oct 8 - Oct 9
Peace & Simplicity in a Little Red Cabin on the Farm
Quite- relaxing country living with pool/hot tub and sauna!
Outdoor pool

Quite- relaxing country living with pool/hot tub and sauna!

10.0 out of 10, Exceptional, (18)
"We had a great time, nice and relaxing. Had everything we wanted."
The price is ￥27,653
￥46,600 total
includes taxes & fees
Oct 5 - Oct 6
Quite- relaxing country living with pool/hot tub and sauna!
Unique Victorian Cottage Close to Town
Exterior

Unique Victorian Cottage Close to Town

10.0 out of 10, Exceptional, (15)
"So convenient, well furnished. Will recommend to all."
Unique Victorian Cottage Close to Town
2 Bedroom Cul De Sac Cottage in Town
Exterior

2 Bedroom Cul De Sac Cottage in Town

9.8 out of 10, Exceptional, (40)
"Enjoyed our time here- great property! "
2 Bedroom Cul De Sac Cottage in Town
Beautiful two story, downtown home, one block from the Square,
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (34)
"Everything was very clean and welcoming. The decor was cute and cozy. Overall great stay."
The price is ￥23,564
￥42,810 total
includes taxes & fees
Oct 8 - Oct 9
Beautiful two story, downtown home, one block from the Square,
MJ's Penthouse ,a piece of paradise on Monroe's historic square
Interior

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

10.0 out of 10, Exceptional, (97)
"In town for girls getaway. This was our second stay at this location. Everything about the stay was perfect will definitely be back! Myron and Jane are great hosts. 10/10!!"
The price is ￥28,667
￥39,922 total
includes taxes & fees
Oct 30 - Oct 31
MJ's Penthouse ,a piece of paradise on Monroe's historic square
Historic Country Farmhouse for ANY Season!
Property grounds

Historic Country Farmhouse for ANY Season!

10.0 out of 10, Exceptional, (45)
"Great weekend with girls. Host was very attentive. Location was great, close to shopping and wineries."
Historic Country Farmhouse for ANY Season!
Duplex overlooking Rock River
Smart TV

Duplex overlooking Rock River

10.0 out of 10, Exceptional, (31)
"very clean. Love this property. We will be back again!"
Duplex overlooking Rock River
KC HOUSE Cozy Country Home. Enjoy the country life!
Exterior

KC HOUSE Cozy Country Home. Enjoy the country life!

10.0 out of 10, Exceptional, (16)
"More than we expected! We were so comfortable and loved every minute being there. We will definitely be back! "
KC HOUSE Cozy Country Home. Enjoy the country life!
Avail. Octoberfest Sep 25th-28th-Lake Cabin w/King
Fridge, microwave, oven, stovetop

Avail. Octoberfest Sep 25th-28th-Lake Cabin w/King

10.0 out of 10, Exceptional, (4)
"This is a beautiful home and area with a lot of fun activities. Love kayaking, playing pool, and sitting on the deck with the lake view."
The price is ￥27,498
￥100,952 total
includes taxes & fees
Oct 13 - Oct 14
Avail. Octoberfest Sep 25th-28th-Lake Cabin w/King
The Rustic Retreat: Elegant cabin with WiFi & AC in an enchanting location!
Interior

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

2.5 star property
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!"
The Rustic Retreat: Elegant cabin with WiFi & AC in an enchanting location!
Relax. Recharge. Reconnect.
Outdoor dining

Relax. Recharge. Reconnect.

2.0 star property
10.0 out of 10, Exceptional, (7)
"We were in town for a volleyball tournament and could not have been happier with our stay here! We felt very safe and welcome and the home owner was very responsive and accommodating. Property is clean and really has that homey feel with lots of natural light and comfortable beds. The shower head is amazing and felt like a massage! This is also in a cute little town with a bar/restaurant just blocks away that has excellent food. We will definitely stay here any time we are in the area. Very...
Relax. Recharge. Reconnect.
Wisconsin Farmhouse Stay: Utv, Boat, Snowmobile!
House (3 Bedrooms) | Interior

Wisconsin Farmhouse Stay: Utv, Boat, Snowmobile!

3.0 star property
Wisconsin Farmhouse Stay: Utv, Boat, Snowmobile!
The Main St Place in charming Mount Carroll IL 1st floor
Exterior

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

9.8 out of 10, Exceptional, (36)
"We had a nice quiet stay. Loved it very much"
The Main St Place in charming Mount Carroll IL 1st floor
Family Friendly Modern Farmhouse 42 Private Acres
Fridge, microwave, oven, stovetop

Family Friendly Modern Farmhouse 42 Private Acres

10.0 out of 10, Exceptional, (8)
"We had a great time relaxing on the spacious screened in porch and cooking out. We and our pupper loved exploring the trails on property."
Family Friendly Modern Farmhouse 42 Private Acres
2br updated private entrance upstairs
Interior

2br updated private entrance upstairs

7.4 out of 10, Good, (3)
"The property was very clean and cozy. It was near all the things we wanted to do during the week. We were very pleased with our stay and would most likely would want to return someday."
2br updated private entrance upstairs
The Main St Place in charming Mount Carroll IL 2nd floor
Smart TV

The Main St Place in charming Mount Carroll IL 2nd floor

10.0 out of 10, Exceptional, (3)
"This property is exactly as pictured! It’s clean and within walking distance of, pretty much, anywhere in Mount Carroll. The owners were quick with communication. I have family in the area, and this will definitely be my first choice for future stays."
The Main St Place in charming Mount Carroll IL 2nd floor
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Freeport Hotel Reviews

Paddle Wheel Inn

Paddle Wheel Inn

10/10 Excellent
"Check in was really easy and convenient. You can tell the property is a little older, but our room was massive. We had a gorgeous view of the river right outside our room. I wish we could've gone on a trip on the local paddle boat, but they have scheduled trip days and hours that didn't correspond with our trip. The sauna was nice and got plenty hot, makes for a specialty that you don't usually find in hotels. 10/10 would stay again. Lovely town too, and great antique stores for any downtime. "
Trebor 2-night trip
Posted 15 hours ago
Paddle Wheel Inn

Find out more about Freeport

Find out more about Freeport

Search for holiday rentals in Freeport on Expedia! You can easily find your home rentals, villas, holiday apartments in Freeport using one of the methods below:

  • View our selection of featured holiday rentals in Freeport
  • Use the map to find apartments and other holiday homes in the Freeport neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Freeport while they last

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 Oscar Taylor Home and Winneshiek Playhouse, 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 Park Hills Golf Course.

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.