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Vacation rentals in Annawan

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Top-rated vacation rentals in Annawan

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
A historic brick building is showcased, featuring ornate arched windows and a decorative façade. The structure includes a ground-level entrance with signage, while bicycles and outdoor seating are visible nearby. Traffic signals and a crosswalk are evident in the foreground.
Apartment in Galesburg
4.92 out of 5 average rating, 606 reviews

Downtown apt. 8

I bedroom apartment in historic downtown building. 2 blocks from Knox College; 3 blocks from Amtrak Station. Several good restaurants and bars nearby; downtown Y a block away. 12' ceilings, hardwood floors, full kitchen and bathroom, coin laundry down the hall. Heat from radiators. Window AC units in summer. TV in bedroom. (For some reason, the listing says 4 beds; that is incorrect.) The apt. is on the 2nd floor: 26 steps. (No elevator.) Parking in lot across the street. Host lives nearby.

Top guest favorite
A small, modern tiny house is nestled among lush green trees. A path lined with wood chips leads to the entrance, where large windows allow for natural light and views of the surrounding forest. A deck extends from the house into the wooded environment.
Tiny home in Princeton
5 out of 5 average rating, 132 reviews

Dana's Retreat-glamping/camping @ a WildlifeRescue

Reconnect with nature at this unforgettable escape. Located at 2nd Hand Ranch & Rescue, this tiny house in the timber was built to share the beauty of nature with folks that want to camp.... but not really camp. This 12x12 house is off grid with a cute outhouse nestled in the timber behind the wildlife rescue. Relax and unplug for the weekend and know 100% of the fee goes to the animal rescue. We bring your supplies up via Gator as you hike the trail up. PLEASE NOTE: NO RUNNING WATER/SHOWERS

Top guest favorite
Home in Hudson
4.98 out of 5 average rating, 142 reviews

Timber Time in Hudson Hideaway

Looking for a break from the busyness of life, to relax and enjoy nature? Step back in time in this tranquil and rustic home. In a remote location and surrounded by timber, this property is perfect to unwind, enjoy a sunset, and view the stars in a wide-open sky. The large yard allows for all kinds of activities and the circle drive provides easy RV, trailer, and boat access. Located next to Evergreen Lake/Comlara Park, the hiking and biking trails, boat ramp, and beach are just minutes away.

Top guest favorite
The charming exterior features a white home with wooden shutters, a welcoming front door, and a small set of steps leading to the entrance. A grassy area surrounds the house, complemented by a gravel pathway that provides access.
Home in Le Claire
4.96 out of 5 average rating, 435 reviews

Aire Leclaire 2-bedroom home

Your family will be close to everything when you stay at Aire Leclaire! Within walking distance from downtown and 2 blocks from American Pickers. This modern 2 bedroom, 1 bath home is a block away from the tugfest parade route. A barnyard turned farmhouse in the 1940’s, this home completely remodeled with the modern farm charm it has today. In town for a day or several, enjoy outdoor amenities, a lighted deck, outdoor couch, and table. Inside, a modern LED fireplace mixed with rustic beauty.

Top guest favorite
A modern cabin is set on a landscaped lot with a gravel path leading to the entrance. The structure features a mix of dark siding and wood accents, surrounded by open fields and distant tree lines, offering a serene rural setting.
Cabin in Princeton
4.96 out of 5 average rating, 162 reviews

Private & Modern. Near river and wildlife refuge!

Experience the outdoors in comfort from this modern cabin, situated next to the 2200 acre Princeton Wildlife Management Area, and the nearby Mississippi River. It is ranked as the most “Wish Listed” Iowa listing of 2025 on Airbnb. Are you into hiking, biking, fishing, hunting, boating, or other water, winter, and summer sports? This cabin can support it all! Sit back and relax on the large deck while enjoying a coffee & the local wildlife, flora, & fauna of the Mississippi Valley Region.

Top guest favorite
The Mill House, a historic green building with yellow trim, features two stories and a stone foundation. The year '1881' is displayed prominently on the facade. A balcony with decorative hanging plants is visible, along with landscaping that includes a signpost and a grassy area.
Apartment in Le Claire
4.93 out of 5 average rating, 304 reviews

Old Mill House - (two bedroom) - on the river!

Historic Leclaire, Iowa is full of quaint shops, antiques, and variety of restaurants. Walking distance (only 175 steps to the Green Tree Brewery), Mississippi River Distillery, Wide River Winery, and the History Channel's ..the American Pickers. Check out our OTHER listing - the "Captain's Quarters" - in the same historic building on the top floor 1 bedroom with king bed! Voted in 2019 River Travel Magazine as one of the top 5 "Most Romantic Getaways" along the Mississippi River.

Guest favorite
A solar-paneled cottage is positioned on a grassy expanse, accompanied by rustic barns in the background. The deck extends from the home, providing a viewing area of the surrounding landscape under a clear blue sky.
Cottage in Princeton
4.93 out of 5 average rating, 164 reviews

Cheerful eco-cottage at Edgewood Farm

Take in old growth oaks, native habitat, Bureau Creek, and rustic barns on 400 acre Edgewood Farm. Nestled in the Bureau Valley, the Eco-Cottage is a solar panel powered fully furnished two bedroom home with modern amenities. Enjoy peaceful morning coffee on the front porch overlooking restored wetlands, prairie, and hardwoods. Walk the miles of farm paths before dining outside under starry skies. Just minutes from Princeton's Amtrak station, antique malls, coffee shops, and bakeries.

Top guest favorite
A spacious living area features mid-century green armchairs, complemented by a stylish coffee table. Light floods in through large windows, accentuating the historic wooden details. The sleeping area is partially visible, showcasing a comfortable bed set against a neutral wall.
Loft in El Paso
4.94 out of 5 average rating, 601 reviews

The Courthouse Loft-History, hot tub, and coffee!

The Courthouse Loft resides in the historic courthouse used in the mid 1900s on the second floor of The City House. The original railing and gate of courtroom divides the 825 soft studio style layout. Loft has a separated bath and laundry and a patio with hot tub! Mid century and historic style will wrap you in comfort and luxury during your stay. We are above a coffee shop, so pop downstairs for breakfast and your morning brew! Oh, and never a cleaning fee!

Top guest favorite
A cozy cottage is set against the backdrop of the Mighty Mississippi River. It features a welcoming red door and a spacious porch furnished with chairs and a table. Well-maintained landscaping includes a lawn, flower pots, and a swing, enhancing the outdoor experience.
Cottage in Port Byron
5 out of 5 average rating, 148 reviews

River Current's Cottage

River Current's Cottage is a hidden gem tucked on the banks of the Mighty Mississippi River. This cozy cottage has magnificent views of the river, no matter what time of year you chose to stay the views & cottage will offer you endless relaxation and enjoyment. With wonderful options for dining just minutes away in Port Byron or driving a few more minutes to LeClaire, IA you can truly make this a relaxing getaway.

Top guest favorite
A driveway leads to a garage with two doors, bordered by manicured grass. A swing hangs from a tree nearby, with open fields visible in the background under a partly cloudy sky.
Home in Roanoke
4.97 out of 5 average rating, 108 reviews

Sage Inn

Charming property conveniently situated between Peoria and Bloomington, IL metro areas. A stone's throw to Roanoke Park and Pool (open seasonally from Memorial Day to Labor Day) including a renowned disc golf course. Amenities include: access to WiFi, full kitchen, Smart TV, Washer/Dryer, Electric Fireplace, Futon in the living room folds out into a queen bed for additional sleeping arrangements.

Top guest favorite
A cozy studio-style space is displayed, featuring a spacious bed with a patterned blanket. A kitchenette with modern appliances is visible, alongside a small dining table and stools. Large windows allow natural light, and a sliding barn door adds a touch of charm.
Guesthouse in Chillicothe
4.96 out of 5 average rating, 225 reviews

River Beach Guest House

Welcome to River Beach Guest House! Where modern meets relaxation! Completely renovated and private 1 bedroom getaway with beach access where you can enjoy beautiful river sunrises and sunsets and eagle watching! Just a 6 minute drive to downtown Chillicothe, 60 minutes to Starved Rock State Park, 18 minutes to beautiful Grandview Drive in Peoria Heights, or just 23 minutes to downtown Peoria.

Top guest favorite
The exterior of a gray, farmhouse-style home is shown, featuring a sloped roof and dark shutters on its windows. Neatly trimmed bushes and grass surround the house, while a wooden fence provides a backdrop in the distance, enhancing the peaceful outdoor setting.
Home in Kewanee
4.98 out of 5 average rating, 193 reviews

Little House in Kewanee

Lovely Farmhouse Style 2 bedroom home located across from park. Newly decorated with fully equipped country style kitchen. The master bedroom has adjustable queen size bed while second bedroom has 2 twin beds. The house is great for a family, two couples or a girls weekend to Historic Bishop Hill or destinations Psycho Silo, Goods Furniture or Horse shoes at Blackhawk College East.

Popular amenities for Annawan vacation rentals

  1. Airbnb
  2. United States
  3. Illinois
  4. Henry County
  5. Annawan