Holiday houses in Freeport

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Top-rated holiday rentals in Freeport

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Cottage in Rockton

4.95 out of 5 average rating, 188 reviews

Country Farm Cottage

Cozy farmhouse Country Cottage on a historic private farm setting. Safe, quiet, peaceful space to relax. Minutes to golfing, hiking, antiques, canoeing, camping, parks, or use as writers retreat. Rockton has great shopping & dining, 20 min to trendy eateries in Beloit WI. Close to local wedding venues Wineries 25 min away May- Nov: orchards cider & donuts Child friendly Visit our Goats Wifi & Roku TVs No Smoking inside No Pets Farm animals and pets on the farm Host lives on same farmstead

23–30 Mar

$318 NZD per night

Guest favourite

Loft in Monroe

4.99 out of 5 average rating, 121 reviews

Loft 3 - On The Historic Monroe Square

Loft 3 is 40 steps (2 flights of stairs) above the Monroe Square. It's a climb, but the view is totally worth it! Newly remodeled in 2021, and reminiscent of the 1859 character of the building, this space is cute, cozy, and truly one of a kind. Literally a couple steps away from your entryway is Sunrise Donut Cafe, featuring customized donuts and a full menu of excellent coffee items. From there, explore the rest of the Square for food, drinks, and shopping in a quaint Main Street atmosphere.

19–26 Jul

$265 NZD per night

Guest favourite

Home in Freeport

4.98 out of 5 average rating, 138 reviews

Willow Lake Getaway Cozy for 2 - or large families

Beautiful 4 bedroom private lakefront home, cozy enough for 2, large enough for family gatherings for holiday/wk end escape/vacations. Hot tub for cool eves October-April. Extensive private decks with BBQ, outdoor dining & circular daybed with umbrella. 2 docks, 2 SUP boards, paddle boat, 2 kayaks, pingpong table, books and board games. 2 Master Suites with smart tv with private balcony & seating area. fire pit located next to 1st dock. Couples get a 10% discount, message me for details.

20–27 Oct

$595 NZD per night

Guest favourite

Cabin in Savanna

4.96 out of 5 average rating, 194 reviews

Cozy, Secluded Cabin -A Peaceful Getaway Location!

Perfectly located: a half mile from town, but secluded enough to be a private hilltop house retreat. The deck overlooks downtown with a backdrop of the Mississippi River! Enjoy the outdoors hiking at the Palisades State Park with miles of trails just a short drive away, kayak or fish one of the many rivers or lakes, stroll through downtown for antique and gift shopping, or visit a nearby winery. After a day of adventures, relax in the spa tub or enjoy a glass of wine on the private deck.

21–28 Feb

$203 NZD per night

Guest favourite

Farm stay in Cherry Valley

4.97 out of 5 average rating, 273 reviews

Bed and Breakfast with Horse Hotel at VRR

Victory Reigns Ranch Horse Hotel and Bed and Breakfast boasts a beautiful ranch setting close to Deer Run Forest Preserve, Oak Ridge Forest Preserve and other equestrian trails. *Come with or without your horse. We also have an RV hookup if needed along with spacious trailer and RV parking. *If interested in horse boarding during your stay a 12 x 12 barn stall is $35 per night. Private pasture turn out available for $25 per horse per night. Trailer hook up is $35 per night per trailer.

24–31 Aug

$184 NZD per night

Guest favourite

Tiny home in Darlington

4.98 out of 5 average rating, 590 reviews

Arbor Crest Cottage- Peaceful farm stay getaway.

Thank you for checking out Arbor Crest Cottage! Jeremiah and I would be happy to host you. We are entering our 5th year of hosting and have been enjoying the experience. Our farmette is conveniently located 2 miles from town, set off the road, and through the woods. The cottage is located on the edge of our woodland area. We invite you to explore our property and enjoy the animals. The west end of our land over looks town and is a great place to watch the sunset and the goats graze.

28 Sep – 5 Oct

$188 NZD per night

Guest favourite

Chalet in Elizabeth

4.91 out of 5 average rating, 289 reviews

Galena Country Getaway

Brick walkway leads to the cedar deck with Adirondack chairs overlooking the large backyard. Enjoy dinner out on the deck and roast marshmallows over a bonfire at the firepit. The dark sky provides excellent stargazing. Kitchen features full-sized refrigerator, cooking utensils and a variety of spices. Spacious bathroom with a waterfall-style shower. Carpeted loft includes a sleep number queen sized bed and two twin beds. Close to Historic Galena & Apple Canyon State Park

30 Sep – 7 Oct

$242 NZD per night

Guest favourite

Cottage in Lena

4.95 out of 5 average rating, 157 reviews

Escape to The Countryside @ Kerlin Schoolhouse!

Welcome to Kerlin Schoolhouse! This Stone Cottage was built in 1870 and was originally a one-room schoolhouse! Kerlin Schoolhouse is located in a quiet, private, peaceful setting in the beautiful countryside. Featuring beautiful views with amazing sunrises, sunsets, windmills, and starry nights! Surrounded by corn fields on all 4 sides. The home features an open concept with loft bedroom & loft-style staircase. Featuring a fireplace, firepit & grill (seasonal), and more.

19–26 Jun

$242 NZD per night

Guest favourite

Tiny home in Thomson

4.86 out of 5 average rating, 349 reviews

Cozy Cabin on the Mississippi River

This cabin is located on the serene backwaters of the Mississippi. It is the perfect destination for a weekend getaway, or ideal spot to rent for fishing tournament‘s or duck hunting. This cabin is situated next to pool 13, and there is plenty of space for multiple vehicles and boats to park. Only half a mile away from the loading dock and close by to an Illinois State Park, our cabin allows Guests to enjoy nature in a relaxed setting.

6–13 Jul

$131 NZD per night

Guest favourite

Barn in Freeport

4.97 out of 5 average rating, 509 reviews

Cute Little Country Guest House

An old barn/machine shed transformed into a great little rustic retreat (which we affectionately call "Westhaven")! A great secluded place to get away from the day-to-day grind. Hiking trails on the premises and possible kayaks. About 5 miles from civilization (town). Come unwind! FRIENDLY DOGS WELCOME (we speak fluent WOOF! :-) ) (Please NO cats!) This is not just a place to stay, but an experience to remember.

12–19 Jan

$191 NZD per night

Guest favourite

Bungalow in Freeport

5.0 out of 5 average rating, 50 reviews

Quaint Bungalow in Central Location

Quaint 2-bedroom bungalow in central Freeport. Wooden floors, large living room with a Smart TV with very fast WiFi, spacious closets, kitchen with quartz counter top fit for a chef. Perfect spot for those in town several days as well as longer (discount for longer stays). We provide coffee and hot cocoa pods for the Keurig and tea. There is a Twin Air Mattress available that can be used in the Living Room area.

13–20 May

$209 NZD per night

Guest favourite

Cabin in Oregon

4.96 out of 5 average rating, 166 reviews

Hidden Gem - Rock River

Escape it all at the Eagles Nest, a cozy, newly renovated cabin on stilts. Located 5 minutes outside of Oregon, Il, the cabin is nestled on 5 acres of of woods with panoramic views of the Rock River and Kyte Creek. Whether you are here to fish, hike, kayak or just escape the city life, you will find the Eagles Nest is the perfect spot for your getaway.

25 Apr – 2 May

$475 NZD per night