Vacation rentals in Freeport

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Top-rated vacation rentals in Freeport

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Guest favorite
The cabin is nestled among tall trees, featuring warm lighting that highlights the rustic wooden structure. A spacious deck extends from the cabin, with a hammock positioned between trees, inviting relaxation amidst nature. Smoke gently rises from the chimney, suggesting a cozy atmosphere inside.
Cabin in Oregon
4.96 out of 5 average rating, 193 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. $33/night per person or pet after first 2 people. Message Tim about accomodating larger groups and events. Closed for winter November through March.

Top guest favorite
A kitchen area features wooden cabinets and a dark refrigerator, with a gas stove and white tiled backsplash visible. A wooden island with seating offers a gathering spot. The room leads to a bright sleeping area, where light floods in through large windows.
Loft in Morrison
4.98 out of 5 average rating, 307 reviews

The Tailor

Beautifully restored 1892 apartment in the heart of Morrison's national historic district offers Victorian elegance with many modern conveniences. Amenities include a full kitchen, washer/dryer, luxurious queen bed, Roku Smart TV, and high speed wi-fi. The 800 sq ft apartment includes original Doug Fir flooring, 10 ft high ceilings, pocket doors, claw-foot tub, custom cabinets and cherry island. Perched above an art gallery, this is the perfect clean and quiet retreat for work or leisure.

Top guest favorite
A wooden swing hangs from a tree in a lush green field, gently swaying in the breeze. In the background, the log home is set atop a hill, showcasing its wrap-around deck and panoramic views of the surrounding landscape under a clear blue sky.
Guesthouse in Stockton
4.98 out of 5 average rating, 397 reviews

HighviewCountry Escape-log home-family farm w/view

Whether you want a staycation or just a weekend away, we have the place for you! Quiet secluded setting, with spectacular view, on one of the highest hilltops in Illinois! Morning sunrises are exceptional. Evening sunsets are breathtaking. Starry nights are amazing. Something in every season! Not far from Galena and other small towns that offer charm, restaurants and shopping. Our rental is fully independent and has everything that you need for your getaway. Please see all photos.

Guest favorite
Home in Freeport
4.99 out of 5 average rating, 205 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.

Top guest favorite
A hot tub is positioned on a deck overlooking a scenic river view. The water's surface reflects soft light, creating a serene ambiance. A lattice privacy screen is visible in the background, framing the peaceful outdoor setting.
Home in Rockford
5 out of 5 average rating, 139 reviews

Adults Only "Red Room" Home with Hot Tub

Unique adult themed home with a BDSM / "Red Room" experience. It's a great way for couples to turn their fantasies into reality and explore with each other. Includes St Andrews Cross, Swing, and Sybian! Relax on the patio or in the hot tub with a scenic view of the Rock River. Once you arrive you will not want to leave so we try to provide you with everything you may need for your stay! Frozen pizzas, Bottled Water, Coffee, Robes, Firewood and a special gift with each reservation.

Top guest favorite
A comfortable seating area features two black reclining sofas positioned around a glass coffee table. A lamp beside the sofa provides soft lighting, while a world map artwork adds a touch of decor to the neutral-toned walls.
Apartment in Byron
4.98 out of 5 average rating, 101 reviews

Location-dining, golf, brewery, parks. We have it

The Loft is an upstairs apartment just a few blocks from downtown Byron, IL and near many local attractions and recreational places/activities. Completely renovated and updated. Clean, bright, and well appointed. This unit has two bedrooms - 1 with a king bed and 1 with a queen bed. There is 1 bathroom with a shower only. There is a washer and dryer in the unit. Please note this unit is on the second floor - with an inside and outside staircase. This property has central heat and air.

Guest favorite
A tiny house cabin is nestled among greenery, featuring a green front door and a small air conditioning unit. Adjacent is an outdoor grilling area with a BBQ grill, a fire pit, and a well-maintained port-a-john, surrounded by pebbled ground and scattered trees.
Tiny home in Savanna
4.97 out of 5 average rating, 130 reviews

"Tiny House" Cabin at Spring Lake Campground

The excitement of camping with all the comforts! Outdoor grilling area with picnic table, queen size bed in the loft, 2 recliners & TV/dvd on main level, AC/heat, sink, microwave & mini fridge. Kitchen service for 2, basic cooking essentials & bedding. Well kept private port-a-john outside cabin and outdoor shower is close by (no bathroom inside cabin) Bring bikes to ride the “Great River Trail”. Camp store & kayak/canoe rentals (through Oct 1st) on site! No pets No smoking please.

Top guest favorite
A charming brick building, enveloped by lush greenery, features a welcoming entrance with a secure door. Large windows framed by ivy provide warmth to the facade. Flower beds with colorful plants offer a touch of vibrancy along the pathway leading to the front door.
Apartment in Edgewater
4.96 out of 5 average rating, 189 reviews

Upscale Urban Retreat 1 Bedroom Apt. 2nd floor

Charm Art Style. Hardwood floors, original woodwork. Secure keypad entry. Spacious cozy apartment with full kitchen and dining room. Owner on adjoining premises. Street parking. Minutes to Sports Factory, downtown nightlife, Japanese Gardens, Rockford Art Museum, Nicholas Conservatory & Sinnissippi Gardens. 5 blocks to river and rec path. Quiet Edgewater Neighborhood District. Ideal for business travelers, couples, solo adventurers and more. Not suitable for children under 6.

Top guest favorite
The exterior of a single-family home is showcased, featuring a two-car garage with turquoise doors. Lush green grass surrounds the driveway, and colorful flowering plants are positioned near the entryway. A clear blue sky serves as the backdrop.
Guest suite in Freeport
5 out of 5 average rating, 108 reviews

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.

Guest favorite
A cozy cabin interior features warm wooden paneling and soft lighting. A brick fireplace adds comfort, while a spacious bed is dressed in a patterned quilt. A inviting sofa and round area rugs enhance the welcoming atmosphere of the living space.
Cabin in Brodhead
4.86 out of 5 average rating, 157 reviews

Cozy Cabin on Decatur Lake

Relax in this cozy cabin on the lake. Fish, hike or even swim (after a short canoe/kayak paddle); just like being Up-North without the drive! Use our canoe or kayaks or bring your own. Cook indoors or out. Near Sugar River Trailhead, Headgates Park and Three Waters Reserve. A few miles away from tubing on the Sugar River. An hour from Madison and 30 minutes from Beloit, Monroe or Janesville. Previously listed by Betty and under her same great management!

Guest favorite
A spacious outdoor deck is featured, surrounded by lush greenery. Several chairs and a table are positioned for seating, with large windows of the cabin visible in the background, allowing natural light to illuminate the interior.
Tiny home in Thomson
4.87 out of 5 average rating, 501 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.

Top guest favorite
Farm stay in Monroe
5 out of 5 average rating, 163 reviews

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.

Popular amenities for Freeport vacation rentals

  1. Airbnb
  2. United States
  3. Illinois
  4. Stephenson County
  5. Freeport