Freeport Vacation Rentals

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Vacation Rentals in Freeport

Apartment in private home, sleeps 7 guest

Freeport
10.0 out of 10, Exceptional, (6)
"Great experience! Hosts are great people. Would stay again if in the area. "
United States
Steve L.
Apartment in private home, sleeps 7 guest

Peace & Simplicity in a Little Red Cabin on the Farm

Lena
10.0 out of 10, Exceptional, (11)
"Quiet, clean and absolutely lovely cabin! "
United States
Holley B.
$160 nightly
The price is $170
Nov 30 - Dec 1
Total with taxes and fees
Peace & Simplicity in a Little Red Cabin on the Farm

Duplex overlooking Rock River

Byron
10.0 out of 10, Exceptional, (34)
"Had a wonderful stay.... the Host was most accommodating and helpful during our stay. Would definitely stay here again. "
United States
Patricia (Patty) M.
Duplex overlooking Rock River

Riverfront cabin on Rock River

Rockford
10.0 out of 10, Exceptional, (206)
"This place was a wonderful place to stay! Very relaxing!"
United States
Ross T.
$269 nightly
The price is $285
Nov 25 - Nov 26
Total with taxes and fees
Riverfront cabin on Rock River

A-Frame Cabin Retreat

2.0 star property
Stockton
A-Frame Cabin Retreat

2 Bedroom Cul De Sac Cottage in Town

Oregon
9.8 out of 10, Exceptional, (42)
"Cozy, clean home convenient location."
United States
Laura G.
2 Bedroom Cul De Sac Cottage in Town

Whispering Woods Estate - Relax, recharge, connect

Rockton
8.8 out of 10, Excellent, (3)
"This was a phenomenal house, couldnt have been any better!"
United States
Cameron S.
Whispering Woods Estate - Relax, recharge, connect

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

Pecatonica
10.0 out of 10, Exceptional, (18)
"Everything was as promised! Smooth and easy check in. Very clean and inviting. Outdoor amenities were in good shape, working and absolutely amazing! "
United States
Gail W.
Quite- relaxing country living with pool/hot tub and sauna!

Avail. Christmas! Lake Cabin w/King, Sauna

Brodhead
10.0 out of 10, Exceptional, (5)
"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."
United States
Jenelle K.
$650 nightly
The price is $686
Nov 24 - Nov 25
Total with taxes and fees
Avail. Christmas! Lake Cabin w/King, Sauna

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

Monroe
10.0 out of 10, Exceptional, (102)
"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! "
United States
Katie B.
$240 nightly
The price is $263
Nov 23 - Nov 24
Total with taxes and fees
MJ's Penthouse ,a piece of paradise on Monroe's historic square

KC HOUSE Cozy Country Home. Enjoy the country life!

Rock City
10.0 out of 10, Exceptional, (17)
"Beautifully maintained, stocked with any little thing you need. Clean, relaxing and suited our group perfectly for a weekend away. "
United States
Patricia M.
KC HOUSE Cozy Country Home. Enjoy the country life!

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

Monroe
10.0 out of 10, Exceptional, (35)
"Everything was very clean and welcoming. The decor was cute and cozy. Overall great stay."
United States
Jeff Z.
$260 nightly
The price is $284
Dec 4 - Dec 5
Total with taxes and fees
Beautiful two story, downtown home, one block from the Square,

Unique Victorian Cottage Close to Town

Oregon
10.0 out of 10, Exceptional, (18)
"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. "
United States
Rob K.
Unique Victorian Cottage Close to Town

Relax. Recharge. Reconnect.

2.0 star property
Winnebago
10.0 out of 10, Exceptional, (8)
"The appliances were all new and worked perfectly.The kitchen was very well stocked.The beds were comfortable.The furniture was new and comfortable.The place was spotless.The hostess was very quickly responsive to any of our questions."
United States
William D.
Relax. Recharge. Reconnect.

Winnebago Spacious Home♥ Beautiful Kitchen LG Yard!!

Winnebago Township
10.0 out of 10, Exceptional, (19)
"Our family had a great time staying in this home. It fit our whole family perfectly and was very clean and nice. Communication was great - an overall very nice experience."
United States
Hayley N.
Winnebago Spacious Home♥ Beautiful Kitchen LG Yard!!

Family Friendly Modern Farmhouse 42 Private Acres

Elizabeth
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."
United States
Colleen C.
Family Friendly Modern Farmhouse 42 Private Acres

Cozy 2-bedroom RV in charming Apple River with AC

Apple River
10.0 out of 10, Exceptional, (1)
"Pretty and quiet area with a clean camper."
United States
jackie l.
Cozy 2-bedroom RV in charming Apple River with AC

Wisconsin Farmhouse Stay: Utv, Boat, Snowmobile!

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

2br updated private entrance upstairs

Rockford
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."
United States
Paul R.
2br updated private entrance upstairs

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.
$286 nightly
The price is $316
Dec 14 - Dec 15
Total with taxes and fees
The Rustic Retreat: Elegant cabin with WiFi & AC in an enchanting location!
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

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 $170 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 Stephenson County Historical Museum 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 Famous Fossil Winery.

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.