Holiday houses in Ashton

"The Coop" on the Farm ! Peaceful & Cozy

💥Please Read Description!💥 No pets 10 min. Hwy 30 90 min. O'Hara 30 min. Dekalb 45 min. Rockford 30 min Oregon The Coop is nestled in a country setting with amenities and a personal chef. 😁 Guest will enjoy modern, country accommodations. Real country brings the thrill of the occasional insect or the sounds and aromas of cutsie critters on occassion. "The Coop" offers a pump-style sink, and a self contained, camp-style lavatory within. Hot Shower is located within the Main House.

Perfect Relaxing Home on Rock River!

Come relax & explore the best of Illinois at our family-friendly RIVERFRONT RETREAT! Stunning 4 bed, 2 bath river escape on acre lot & river frontage/access. Main floor is spacious & cozy updated eat in kitchen, full bathroom, living room & dining room. Enjoy large deck with BBQ, river views, and backyard fire pit. 4 beautiful bedrooms and 2nd full bath upstairs. Location is perfect minutes from everything! Whether you are here to hike, canoe, fish or escape the city life, we have what you need.

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.

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

The Corner Cabin

The cabin has a view of the peaceful Rock River. Very relaxing & cozy. Minutes from Castle Rock State Park. Enjoy canoeing, fishing, & hiking trails. Reconnect with nature, play a board game, barbecue, watch the birds & engage in outdoor activities. Enjoy exploring the quaint small towns, antiquing, & local restaurants. Go from city life to country life, just “90” minutes from Chicago. This is a great place to relax & unwind. Due to location & your carrier you must be patient with our WiFi.

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.

Cozy Cottage Oasis in Charming Grand Detour

This rustic 3 bedroom country house hosts a relaxing getaway & friendly gatherings. Settled on 2 acres in a quaint, historic village, there are no street lights and unfiltered views of the stars. Get away from the crowds, relax & enjoy ample outdoor space, including a fire-pit and charcoal grill. Hike, canoe, and explore the nearby rolling hills, forests & river valleys. Close to John Deere, Lowden and Castle Rock State Park, and Nachusa Grasslands. 10 min drive to Dixon and Oregon IL.

Hidden Gem of Sycamore

Keep it simple at this peaceful and centrally-located place. Located just 3 blocks/5 minute from downtown. Walking distance to Blumen Gardens and The Regale Center. Apartment is above garage in the historic district of Sycamore. Private laundry room is available to guests and free of charge. If you’re coming for the car show in July we are just 1 block from where the car display starts. Sycamore Steam Show is approximately 7miles/15 minutes. City park is 1 block from apartment.

LHOTP (Lil House On The Prairie)

Lil House On The Prairie (LHOTP) is aptly named because it’s located on the edge of Nachusa Grassland’s 1,000 acre south Bison pasture. The 100+ herd of free ranging Bison can often be viewed right along the boundary fence to the west! This recently remodeled two bedroom cottage can sleep six with two queen size beds and with a pull out sofa bed. LHOTP offers a quiet, convenient, and comfortable place to base your adventures from. Behaved dogs & responsible owners welcome!

Historic Cottage Walk to Downtown & Trails

Step into a restored 1875 Victorian cottage just a short walk from downtown Oregon, IL. Thoughtfully decorated to create a warm, inviting escape with vintage charm. Relax on the porch, explore nearby nature, or enjoy local restaurants, a brewery, shops, and scenic views. Ideal for couples, solo travelers, small groups, and those visiting for work or longer stays near Woods, Etnyre, the Byron plant, and KSB Hospital. Also used as a filming location for multiple productions.

Enjoy a visit to Mini Mansion

Walking distance to downtown Sterling but settled in a quiet residential block this unique 1 bedroom apartment has everything for a quick stay to a long work visit. All in one washer dryer, Electric Range, Full Size Fridge and plenty of cabinet space compliment the Kitchen. Spacious Living Room with Daybed for an extra guest or seating and vintage pocket doors separating the bedroom outfitted with King Bed are just a few of the unique features of this ground floor unit.

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!