Holiday rentals in Freeport

Home away from home, downtown Freeport

Beautiful historic building that’s walking distance to bars, restaurants, weddings venues, music, parks with many activities. Walking/biking distance from the Jane Adam’s trail, we have 2 bikes available for you to use. Dog park is 10 minute’s away Well stocked apartment, kitchen has utensils, pots and pans, microwave, coffee pot, toaster oven, refrigerator and stove. Smart TV and internet. Is a great setup for longer term guests. Ground level, free parking in a private lot at the back door.

Family · Location · Getting around

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.

Location · Family · Layout

Adults-only Red Room retreat with HotTub

Adults-only private getaway on the Rock River with a hot tub, patio, and one-of-a-kind Red Room experience. Perfect for couples wanting privacy, comfort, and something more adventurous than a typical stay. Relax with a scenic river view, enjoy the hot tub, then explore a playful adult-themed space with a St. Andrews Cross, swing, Sybian, and more. Designed for birthdays, anniversaries, date nights, or a private weekend that feels secluded, romantic, unforgettable, and anything but ordinary.

Location · Value · River

Historic Randall Schoolhouse

You'll love this beautifully redone Historic One-room Schoolhouse. Situated on the edge of the Driftless area 5 miles from the Sugar River Trailhead. An easy 30 minutes to Monroe, Beloit & Janesville and just an hour outside Madison. Relax in comfort with all new appliances including a full kitchen, washer/dryer, dishwasher and fireplace. Fenced yard. Just a mile down the road from a working homestead where you can milk a cow, pet a goat, harvest fresh produce and eggs and so much more.

Family · Location · Outdoor spaces

Lower Level Suite in Home-Private Entrance!

⭐️ Large lower level walk out apartment for up to 7 people, ⭐️separate entrance in single family home in a quiet upscale neighborhood. 💡Lighted sidewalk. ⭐️Gas in wall heater supplements heating needs in winter. Sleeps up to 7 guest with 🛌1 king bed (heated mattress pad) in master, common area has 🛌 4 Twin XL beds w/memory foam mattresses and 🛌 1 additional Twin XL bed in bonus room. ⭐️ Free Washer/Dryer in apt. w/3 courtesy soap pods. 👶🏻 Pack n Play 🍼 high chair.

Value · Location · Hospitality

Updated 3BR Home | King Bed & Fenced Yard

There’s something special about a place that instantly feels like home. The Gilded Cottage is a beautifully updated 3-bedroom mid-century retreat in Winnebago, IL. Enjoy comfortable beds, quality linens, inviting gathering spaces, a kids’ play area, fenced backyard, and EV charging. Peaceful yet convenient to Rockford area attractions, wedding venues, parks, and nature preserves, an easy home base for family visits, getaways, and special occasions.

Family · Location · Indoor spaces

The Dairy at the Wegmueller Farm

Welcome! You are about to experience life on an active 4th-generation farm nestled in the rolling hills of Green County. Meet the cows, feed the pigs, befriend a horse, or just enjoy the relaxing and peaceful serenity of rural Wisconsin farm life. Located less than five miles from Monroe, this home away from home is close enough to all that Monroe & the surrounding community has to offer, but still has room to stretch your legs.

Location · Value · Bathroom

Hidden Gem - Rock River

The Eagle’s Nest: A Cozy Family Escape! Unplug and unwind at The Eagle’s Nest, a renovated cabin on stilts nestled on 5 private wooded acres with stunning views of the Rock River and Kyte Creek—just 5 minutes from Oregon, IL! Hike, fish, kayak, or relax by the firepit under the stars. Perfect for families and outdoor lovers, this peaceful retreat offers adventure and tranquility. Book now and escape the city hustle!

Family · Location · Layout

Las Lomas Luxury Home.

Kick back relax and experience the best of two worlds, the luxury and comfort of a 5 star hotel and the warmth and peace of feeling right at home. This stylish space offers a variety of books to read and a wonderful jet tub to enjoy after a long trip or day at work; along with clean and cozy beds. Take advantage of our welcome coffee bar with a nice selection of teas and snacks exclusive for our guest.

Location · Value · TV

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. 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.

Location · Family · Outdoor spaces

Welcome to the "Bat Cave"!

Completely renovated 3 bedroom, 2 bathroom home with walk in basement allowing easy access for ATV and snowmobile enthusiasts. Direct access to the Cheese Country trail and one block from The Vault and Cash's bar and grill! Amenities include washer and dryer, wifi, 3 smart TV's and a unique gathering spot with poker table in the basement.

Location · Value · Checkout

Peaceful Cabin Escape • Stargazing & Nature

🌲 Peaceful country cabin retreat 🌲 Soaking tub for ultimate relaxation 🌲 Cozy loft with twin beds 🌲 Recreation room with bar & lounge 🌲 Quiet rural setting perfect for stargazing 🌲 Queen bedroom on main level 🌲 Fully equipped kitchen 🌲 Grill for outdoor dining 🌲 Fast WiFi & keyless entry 🌲 The perfect place to unplug and unwind

Value · Location · Quiet