Vacation rentals in Freeport

Charming 1930s "Kinsey Farms" Cottage

Your family will be close to everything when you stay at this centrally-located place. Easy highway access and less than 10 minutes from downtown - all the fun Rockford has to offer! Located on a quiet, dead end street. Walk to the playground at Ken-Rock park! Several stores/restaurants nearby. One hour drive to Chicago O'Hare airport, and only 3 miles from Rockford Intl Airport. Lots of recreation in the area including Rock Cut State Park, Anderson Japanese Gardens, and Klehm Arboretum. LGBTQ+!

Doe Meadow, a tiny house farm stay

Doe Meadow is my newest custom designed tiny house nestled along the drive to my family farm. Sharing my little slice of heaven with guests is something I have found great joy in. Rural tourism is my passion, & all the farm animals are anxiously awaiting your visit- treats in tow- of course! I wanted to create something unique, a place to make memories, & somewhere you'll want to come back to. Settle in the hammock, listen to the peaceful wind chimes, watch the goats & mini cows graze, unwind.

Hot Tub+ Firepit+ "Tiny"house+ Views+ Near Galena

Tucked away in the countryside of Galena, our charming A-frame cabin is the perfect escape for those seeking peace, nature, and a touch of nostalgia. This intimate retreat blends mid-century modern charm with cozy modern comforts, creating an unforgettable getaway. Whether you’re sipping coffee on the deck at sunrise, soaking in the brand-new hot tub under a canopy of stars, or unwinding by the fire with a vinyl record spinning in the background, every moment here is designed for relaxation.

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.

Adults-only Red Room retreat with hot tub

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.

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.

Walk everywhere in downtown Freeport.

Downtown Freeport, walking distance to movies, bars, restaurants. Some of the summer activities include concert on the square once a month, market every Saturday. The largest car show with 1000 old cars, the air show. If you like to walk or ride a bike there’s Jane Adam’s trail. Krape park is beautiful with many trails on the river where you can rent kayaks. The kitchen is apartment sized but boasts a counter top induction cook top, oven, microwave, Keurig,and refrigerator.

3BR Home Brand New Kitchen and Bath

There’s something special about finding a place that instantly feels like home. The Gilded Cottage is a beautifully updated three-bedroom mid-century retreat in Winnebago, Illinois. It is bright, peaceful, and designed for easy stays. Enjoy quality linens, inviting gathering spaces, and a dedicated kids’ play area. Close to Rockford attractions, wedding venues, and nature preserves, it’s a calm, comfortable home base for any visit.

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.

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.

Howardsville Schoolhouse

This lovingly restored schoolhouse blends history with modern comfort. Set in a peaceful rural location, it features an open living area, fully equipped kitchen with seating for 12, and cozy sitting area with fireplace and play area. Enjoy a spa-like bath with clawfoot tub, king bedroom, and laundry. A perfect mix of new, refurbished, and antique details create a unique, inviting retreat.

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