Holiday houses in Oregon

5 out of 5 average rating, 45 reviews

Home in Oregon

Unique Victorian Cottage Close to Town

This 1875 Victorian cottage offers a blend of history and comfort. Lovingly decorated, this home provides a peaceful escape filled with vintage charm. It was even used as a filming location for a Hulu show! Relax on the porch, explore nearby nature, or unwind with movies, books, and games. Downtown restaurants, brewery, shops, and scenic views are a short walk away. Ideal for couples, solo travelers, small groups, and business travelers. Nearby: Woods, Etnyre, the Byron plant, and KSB Hospital.

4.89 out of 5 average rating, 327 reviews

Home in La Moille

Cozy & Quiet Living at the Cookie Cottage

Welcome to the Cookie Cottage! This is the perfect place to disappear from the busy world for a bit. This home is so special to me and I am happy to be able to share it with you. Located in the small town of La Moille, IL - population 700. It's a 2 bedroom with so much vintage charm. Updated in all the best ways with all new beds, bedding, 43 inch Smart TV, Ring Camera, wifi thermostat and 2 Echo Dots. Surrounding towns offer entertainment, restaurants and more with just a short drive. NO CATS

4.97 out of 5 average rating, 154 reviews

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.

Farm stay in Cherry Valley

4.97 out of 5 average rating, 364 reviews

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.

4.97 out of 5 average rating, 61 reviews

Guest suite in Oregon

Cozy 2-BR home-apartment in a park-like setting.

This charming home-apartment provides all of the comforts of a modern home in a cozy setting. It includes refinished oak floors, new appliances, and other stylish finishes. Your private entrance opens to a kitchen with all of the amenities, including a new stainless gas range. Bedrooms are tastefully decorated and quite comfortable. Includes wifi with television and movie subscription services. Dine outdoors with your private picnic table, firepit, & grill in a beautiful, wooded setting.

4.98 out of 5 average rating, 751 reviews

Tiny home in Darlington

Arbor Crest Cottage

Thank you for checking out Arbor Crest Cottage! Jeremiah and I would be happy to host you. We are entering our 5th year of hosting and have been enjoying the experience. The farmette is conveniently located 2 miles from town, set off the road, and through the woods. The cottage is located on the edge of our woodland area. We invite you to explore our property and enjoy the animals. The west end of our land over looks town and is a great place to watch the sunset and the goats graze.

4.94 out of 5 average rating, 64 reviews

Cottage in Oregon

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!

Cottage in Franklin Grove

4.94 out of 5 average rating, 177 reviews

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!

4.96 out of 5 average rating, 181 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. $35/night/person/pet after first 2 people. Message Tim about accomodating big groups and events.

4.96 out of 5 average rating, 214 reviews

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!

4.97 out of 5 average rating, 554 reviews

Barn in Freeport

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 and possible kayaks. 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.

5 out of 5 average rating, 21 reviews

Home in Oregon

7-11 3rd Street

Enjoy your stay at 7-11 3rd Street in Oregon, IL ! Tucked at the edge of Oregon, close to Mix Park and Alfano's restaurant. Mix Park has a playground, shelter and Pickle Ball Courts. Pickle Ball paddles are provided in the mud room for your use. After a day at the park, enjoy our spacious deck! Choose from two comfy bedrooms to relax or a warm fire in the fireplace to wind down. No pets allowed.

Holiday rentals for every style

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Cabins

Kick off your hiking boots at these rustic lodgings

Hotels

Stylish accommodation and amenities

Unique stays

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Popular amenities for Oregon holiday rentals

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Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Oregon

5 out of 5 average rating, 39 reviews

Cabin in Beloit

A-Frame River Wellness Retreat: Sauna & Hot Tub

JoeRating, 5 stars1 week ago

The cabin was spacious, clean, and lovely. So many incredible amenities, particularly the hot tub. Lovely and quiet surroundings leading down to the river. Just awesome.

4.92 out of 5 average rating, 36 reviews

Cabin in Pearl City

Getaway cabin w/loft & firepit @The Rustic Retreat

DanielaRating, 5 stars2 weeks ago

We loved our stay! The cabin was affordable, clean & even better in person. My kids had a great time & as a not-so outdoorsy family, it gave us the perfect balance of comfort & nature. Highly recommend!

5 out of 5 average rating, 19 reviews

Apartment in Freeport

Walk everywhere in downtown Freeport.

LukeRating, 5 stars6 days ago

A fantastic price for a convenient location! The inside is spacious with all the amenities you could need. The outside can look a bit uninviting, but the room itself, as well as Judy, were fantastic!

4.84 out of 5 average rating, 103 reviews

Summer Cabin Family Getaway: Pine Creek Escape

NicoleRating, 5 stars2 months ago

I really enjoyed my stay! Everything was great, I will definitely be booking again.

Home in Dixon

4.73 out of 5 average rating, 136 reviews

Cozy Cottage Oasis in Charming Grand Detour

ChrisRating, 5 stars2 weeks ago

Great place to stay close to family and the dog activities we were in town for. We have stayed many times and always find the place clean and welcoming.

Apartment in Rochelle

4.84 out of 5 average rating, 235 reviews

Urban Elegance, Small Town Charm Suite #1

LisaRating, 5 stars2 weeks ago

Such a great little spot downtown, close to restaurants and shopping, and incredibly easy access.

4.88 out of 5 average rating, 86 reviews

Apartment in Sterling

Downtown Red Door Secret

CoreyRating, 5 stars1 week ago

Brian was a great host. On Friday night there was some pretty loud music till about 2 am- but in the morning the owner of the bar apologized and explained they were doing a fund raiser to benefit a local family. The location is right downtown and close to everything. Air Play Coffee and Bakery next door is nice. The Precinct Pub less than a block has a decent menu and quaint pub. The year around Farmers Market is 3 blocks. Overall- Brian’s Red Door Air BnB was perfect for us.