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 · Parking

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.

Family · Value · Check-in

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 · Value · Accuracy

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 · Outdoor spaces

The Fishbowl

Welcome to this cozy one bedroom, one- bath retreat just steps from downtown Monroe and the historical square. Perfect for couples, small families, or business travelers, this space blends comfort, style, and convenience. The living room includes a spacious sectional sofa, providing extra sleeping space for children or additional guest while still offering plenty room to relax. The main bedroom is complete with a king size bed, fireplace, large screen TV, and a dedicated workspace.

Location · Value · TV

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 · Family · Outdoor spaces

MJ's Penthouse ( A piece of paradise in Monroe)

A beautiful 2000 square foot second floor Penthouse that offers an excellent view of the historic court house and square. Our location gives you walking distance to all places on the square including the 2nd oldest brewery in the country, boutiques, hair and nail salons, home decor , antique shops, clothing and apparel, specialty treats, restaurants and bars. We have free parking out front on the square and also a private elevator for our guests special needs.

Location · Value · Cleanliness

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 · Amenities

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 · Grill

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.

Family · Value · Hospitality

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 · Solo travel

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

Location · Value · Wifi