Holiday houses in Freeport

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Top-rated holiday rentals in Freeport

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Guest favourite

Cabin in Oregon

4.95 out of 5 average rating, 151 reviews

GOOSE ISLAND CABIN -Secluded Riverside Eco-Retreat

Nestled along the banks of the Rock River under tall oaks, ye ol cabin was built by early settlers in 1907. Legit rustic charm. Secluded yet only 10 mins from the fun town of Oregon. 100 acres of private property, bordering Lowden-Miller State Forest. Includes use of canoes/kayaks, large riverfront yard, grills, hammocks, deck, porch and firewood. Pets allowed by adding them to total guest count. $35/night/person/pet after first 2 people. Message Tim about accomodating big groups and events.

Guest favourite

Loft in Monroe

4.99 out of 5 average rating, 124 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.

Guest favourite

Cabin in Oregon

4.97 out of 5 average rating, 135 reviews

The Corner Cabin

The cabin has a view of the peaceful Rock River. Very relaxing & cozy. Minutes from Castle Rock State Park. Enjoy canoeing, fishing, & hiking trails. Reconnect with nature, play a board game, barbecue, watch the birds & engage in outdoor activities. Enjoy exploring the quaint small towns, antiquing, & local restaurants. Go from city life to country life, just “90” minutes from Chicago. This is a great place to relax & unwind. Due to location & your carrier you must be patient with our WiFi.

Guest favourite

Home in Freeport

4.98 out of 5 average rating, 141 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.

Guest favourite

Cabin in Savanna

4.97 out of 5 average rating, 205 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.

Guest favourite

Farm stay in Cherry Valley

4.97 out of 5 average rating, 283 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.

Guest favourite

Farm stay in Argyle

4.98 out of 5 average rating, 255 reviews

Rustic Barn Loft at Oak Springs Farm

Unplug in our gorgeous barn loft above our working barn. Sleep to the sound of crickets and frogs in the pond, then wake up and pet the sheep, goats, rabbits, cats, ducks & chickens. Open floor plan, cathedral ceiling, farm decor, fire pole, sliding barn doors. Full kitchen, jetted tub, rain shower, laundry. Stone patio, fire pit. 2 bedrooms, sleeper sofa, air mattresses. Juice, coffee, and fresh eggs provided when the hens are laying. NO A/C. ABSOLUTELY NO PETS Facebook oakspringsfarmwi

Guest favourite

Guesthouse in Mineral Point

4.94 out of 5 average rating, 189 reviews

Lumber Yard Cottage, a cozy retreat

The Lumber Yard Cottage is a cozy hidden retreat tucked away from the road. Within walking distance of all Mineral Point has to offer. Great restaurants on all sides of this property and wonderful shops are just up the road. The Cheese Trail and railroad museum are across the street. Enjoy the back porch with the wraparound stone wall or the lovely front porch and watch the world slowly drift by. There is a queen size bed, jacuzzi tub, gas fireplace, ac unit, full kitchenette, and wi-fi.

Guest favourite

Chalet in Elizabeth

4.91 out of 5 average rating, 294 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

Guest favourite

Cottage in Lena

4.95 out of 5 average rating, 157 reviews

Countryside Getaway at 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.

Guest favourite

Tiny home in Darlington

4.98 out of 5 average rating, 255 reviews

The Bower- Peaceful farm stay getaway.

Thank you for checking out The Bower at Arbor Crest Acres! We would be happy to host you! This is our 5th year hosting and our 2nd tiny cottage. Our farmette is conveniently located 2 miles from town, set off the road, and through the woods. The Bower is just inside our property on the edge of the woods. 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.

Guest favourite

Tiny home in Thomson

4.86 out of 5 average rating, 355 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.