Holiday rentals with outdoor seating in Ogle County

4.9 out of 5 average rating, 41 reviews

Cozy 2-bedroom home in convenient Oregon location

Sitting in the Rock River Valley, Oregon, Illinois is a charming town with much to offer visitors. Three state parks full of hiking trails are nearby. Rent canoes or kayaks to float down the scenic Rock River. Walking distance from our home is Park West with a trail, tennis courts, play area, splash pad and a sledding hill. Downtown Oregon's restaurants, bars and stores are a short drive or a pleasant walk. For business travelers, the Byron plant, Woods, Etnyre and KSB Hospital are short drives.

5 out of 5 average rating, 14 reviews

Home in Byron

Insta-worthy Rock River cabin

Take it easy at this unique and tranquil river cabin featuring one of the best outdoor spaces of any home on the Rock River. This outdoor area has plenty of space underneath the second-floor main composite deck to entertain guests or enjoy family meals. It is complimented by a contemporary stone patio with a fire pit, surrounded by 8 Adirondack chairs. Short drive to historic Oregon or the lively town of Byron. This home is tastefully decorated, updated & modern. Perfect for remote workers.

5 out of 5 average rating, 86 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, Slippers, Robes, Firewood and a special gift with each reservation.

4.92 out of 5 average rating, 78 reviews

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.

5 out of 5 average rating, 45 reviews

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.

4.97 out of 5 average rating, 154 reviews

Cabin in Oregon

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.

4.97 out of 5 average rating, 72 reviews

Home in Rochelle

Little Blue Charmer 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! Quiet neighborhood! Budget Friendly for Families! 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!

4.97 out of 5 average rating, 63 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.

4.94 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!

4.94 out of 5 average rating, 16 reviews

Gorgeous Sprawling Acreage w/ Stunning Views

Soak up the sprawling valley views from the wrap around front porch in this beautifully redesigned farmhouse. From the moment you arrive, the calm, peaceful location will melt away stress. Sit by the fire pit, enjoy miles of private walking trails on the property, or just sit on the porch and take it all in. Just a few miles from everything including grocery stores, restaurants, shopping, golf, wedding venues, bison, entertainment and more. Ample parking for trailers.

4.98 out of 5 average rating, 40 reviews

Guesthouse in Byron

Duplex Overlooking Rock River

This home has been remodeled with new flooring, appliances and fresh paint. It overlooks the Rock River with gorgeous views and a walking/bike trail. It has a central location to Prairieview Golf Course, Motosports Park, Harry Cow Brewery, Uptown Lanes, Cave Inn, and various other bars and restaurants - many within walking distance. There is WiFi with streaming capabilities. Each bedroom has black out curtains and a tv. There is also a new washer and dryer.

4.96 out of 5 average rating, 182 reviews

Cabin 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. $35/night/person/pet after first 2 people. Message Tim about accomodating big groups and events.

Holiday rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodation and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Ogle County outdoor seating rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with Outdoor Seating

4.75 out of 5 average rating, 4 reviews

Eagles Den

StaceyRating, 5 stars1 day ago

We had an amazing time at the Eagle’s Den. It was a perfect getaway from the hustle and bustle of the big city. Check-in was super easy and Bren responded quickly to all questions we had! We would definitely stay here again!

Superhost

GregRating, 5 stars12 months ago

Quiet country living yet close to town & hospitals

Melissa was a great host! She communicated great and was very prompt on any communications or questions! Her save was clean and quiet and met all of our expectations! I would recommend her house and her as a host to anyone! We enjoyed our stay!

Superhost

5 out of 5 average rating, 5 reviews

Newly updated Rockford house!

DawnRating, 5 stars1 month ago

The house was very nice, clean and good location for a little more room needed. I enjoyed our time and had plenty of room for my husband and myself. Julie the host was super responsive and helpful. The book that was provided was extremely useful and instructions clear. I would definitely recommend and stay here again.

4.84 out of 5 average rating, 32 reviews

2 Bedroom Cul de Sac Cottage in quiet area of town

AndreaRating, 5 stars1 week ago

Very nice location and place to stay. While our time was short, we enjoyed the space.

4.54 out of 5 average rating, 26 reviews

RiverView Cottage

SusanRating, 5 stars1 week ago

Great price, great views, nice neighborhood, excellent quick host response to check-in questions!

Home in Dixon

4.73 out of 5 average rating, 137 reviews

Cozy Cottage Oasis in Charming Grand Detour

RhondaRating, 5 stars2 weeks ago

This air bnb suited our purposes perfectly. It was just the right amount of space and the bed was comfortable. We enjoyed having a fire with our young granddaughters and we loved the location. Such a beautiful place to take a long walk enjoying nature.

4.97 out of 5 average rating, 65 reviews

Comfy 3-bedroom home backed by a forest preserve

DeenaRating, 5 stars5 months ago

Everything was great! Patrice's home was exactly what we were looking for. Our only regret is that it was December and we were not able to use the wonderful outdoor space. Thank you for opening your home to us!