Holiday houses in Oregon

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.

Skip & Reed's River Retreat

Wonderful riverfront home located just south of Castle Rock on the Rock River in Oregon, IL. Enjoy beautiful views of the river while enjoying the heated pool (open May 15th through Oct 10th). Enjoy fishing off the lower yard. Must love cats as there are friendly outdoor cats! The Oregon area has plenty to do including exploring the nearby state parks, climbing Castle Rock, visiting John Deere's home, antiquing, tubing and boating down the river & enjoying the quaint area shops & restaurants.

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.

Splash of Swedish in an Exposed Basement Apartment

Nestled in a family friendly neighborhood, this lower unit with private entrance, offers a quiet stay with friendly neighbors. Fast Wi-Fi and Television with a Peacock subscription are provided. Located near highway 20 offers easy access to the airport and highways 39 and 90. The home is 4 min away from Atwood Park, providing miles of scenic hiking and a rescued bird aviary. A 13 min drive gets you to downtown Rockford with numerous shops, museums, restaurants and views of the Rock River.

Bed and Breakfast with Horse Hotel at VRR

Victory Reigns Ranch Horse Hotel and Bed and Breakfast boasts a beautiful ranch setting close to Deer Run Forest Preserve, Oak Ridge Forest Preserve and other equestrian trails. *Come with or without your horse. We also have an RV hookup if needed along with spacious trailer and RV parking. *If interested in horse boarding during your stay a 12 x 12 barn stall is $35 per night. Private pasture turn out available for $25 per horse per night. Trailer hook up is $35 per night per trailer.

Look at the reviews! Julie's House on Main

Super Clean, Quiet and Cozy! Pet friendly... 🐾 🐕 ❤ 🐶 (Applicant + Fee required) 90 mi to Chicago! 2 hrs to the Dells! 5 min west of Hwy 39/51 15 min to NIU 45 min to Rockford Walking and bike trail nearby! Beautiful home! Super clean! Monday-Sat check: 3 PM Sunday Check-In: 5 PM Our eight-jet power shower will relax those tired muscles after a full day of activity. A soak in our modern free-standing tub will sooth and your worries away. A well stocked kitchen awaits you!

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.

Spacious Hillside Home Overlooking Private Woods

Guesthouse available for added fee and sleeps 2 with an extra bathroom. Separate access code needed. Please denote in reservation if you'd like to add! We created this space with the hope of sharing it as a place of retreat and refocus. The house sits on 6 acres of private woodland for you to enjoy. Whether walking through the trees, sitting by campfire at the top of the sandstone overlook, or watching the birds and deer, we hope you’ll reconnect with nature and enjoy your time!

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!

Upscale Urban Retreat 1 bedroom, ground Floor

Charming and beautiful ground floor; wood floors and original woodwork. Secure keypad entry. Owner on adjoining premises. Minutes to Indoor Sports Factory, downtown nightlife, restaurants, shops, Japanese Gardens, Rockford Art Museum, Nicholas Conservatory and Sinnissippi Gardens.. 5 blocks to river and rec path. Centrally located quiet Edgewater Neighborhood District. Ideal for business travelers, couples, solo adventurers and more. High speed internet.

Urban Elegance, Small Town Charm Suite #1

Lovely, quaint, and full of urban elegance yet all set in a charming small town setting. Amenities of a luxury boutique hotel, yet the low price of a standard room. Complete with WiFi, The kitchen does not have a stove but does host a small fridge, microwave, toaster oven, coffee maker, dishes. Separate living room with Record Player & Vintage Albums. Luxury Bed in a relaxing space. Workspace so you can conduct your business.

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!