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Freeport Vacation Rentals

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Vacation Rentals in Freeport

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

10.0 out of 10, Exceptional, (199)
"We had a great stay! Nice property with peaceful surroundings and everything you need. Would 100% stay again. "
$269 nightly
The price is $285
Oct 12 - Oct 13
Total with taxes and fees
Riverfront cabin on Rock River

Whispering Woods Estate - Relax, recharge, connect

8.0 out of 10, Very Good, (2)
"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

10.0 out of 10, Exceptional, (8)
$138 nightly
The price is $146
Oct 13 - Oct 14
Total with taxes and fees
Peace & Simplicity in a Little Red Cabin on the Farm

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."
$301 nightly
The price is $319
Oct 9 - Oct 10
Total with taxes and fees
Quite- relaxing country living with pool/hot tub and sauna!

Unique Victorian Cottage Close to Town

10.0 out of 10, Exceptional, (15)
"This was the perfect choice for us. The proximity of the house was great; could walk to many things. The house was charming and inviting. Would love to book this again in the future. "
Unique Victorian Cottage Close to Town

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,

10.0 out of 10, Exceptional, (34)
"Everything was very clean and welcoming. The decor was cute and cozy. Overall great stay."
$279 nightly
The price is $306
Nov 4 - Nov 5
Total with taxes and fees
Beautiful two story, downtown home, one block from the Square,

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

10.0 out of 10, Exceptional, (97)
"My husband and I stayed here and were so happy we did this home was beautiful and really something special. I highly recommend the stay here! "
$248 nightly
The price is $272
Oct 12 - Oct 13
Total with taxes and fees
MJ's Penthouse ,a piece of paradise on Monroe's historic square

Historic Country Farmhouse for ANY Season!

10.0 out of 10, Exceptional, (46)
"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

10.0 out of 10, Exceptional, (32)
"very clean. Love this property. We will be back again!"
Duplex overlooking Rock River

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

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."
$647 nightly
The price is $682
Oct 13 - Oct 14
Total with taxes and fees
Avail. Octoberfest Sep 25th-28th-Lake Cabin w/King

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.

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!

3.0 star property
Wisconsin Farmhouse Stay: Utv, Boat, Snowmobile!

Private Studio whole unit

Private Studio whole unit

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

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

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
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

Find out more about Freeport

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 $146 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.

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.