Holiday rentals in Ogle County

5 out of 5 average rating, 13 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.

4.92 out of 5 average rating, 76 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, 44 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

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, 60 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.

4.97 out of 5 average rating, 76 reviews

Flat in Byron

Location-dining, golf, brewery, parks. We have it

The Loft is an upstairs apartment just a few blocks from downtown Byron, IL and near many local attractions and recreational places/activities. Completely renovated and updated. Clean, bright, and well appointed. This unit has two bedrooms - 1 with a king bed and 1 with a queen bed. There is 1 bathroom with a shower only. There is a washer and dryer in the unit. Please note this unit is on the second floor - with an inside and outside staircase. This property has central heat and air.

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!

4.96 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.

5 out of 5 average rating, 9 reviews

Guest house in Rockford

Shelby’s garden cottage.

Shelby’s cottage has been part of Bluffs on the bend farm for over 65 years. It has undergone a complete overhaul and update with all the modern conveniences while retaining a country cottage charm. It is the perfect getaway for a couple. The location is next to the historic ( originated in 1924 ) Kilbuck Bluffs Forest Preserve. While being nestled in the country it is centrally located to restaurants , bars and shopping.

4.96 out of 5 average rating, 213 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!

5 out of 5 average rating, 21 reviews

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.

4.92 out of 5 average rating, 74 reviews

Dam River House

Enjoy a secluded, cozy stay nestled right on the Rock River. Located conveniently in town, close to amenities within walking distance to downtown food & shops. Explore the outdoors with river access for fishing & kayaking/canoeing/tubing. Relax & unwind in the hottub overlooking the best river front views in town!

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Popular amenities for Ogle County holiday rentals

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Other great holiday rentals in Ogle County

Cabin in Byron

4.86 out of 5 average rating, 22 reviews

Restore Retreat on Rock River

LeviRating, 5 stars1 month ago

This place is excellent for a weekend getaway. I want to bring my organization here for our retreat in the future. Great place to get away for a bit and reset. The cabin feel is great and plenty of great communal spaces to be with friends or family. The kitchen area was accessible and great to use for our breakfast. Highly recommend the local golf course too.

Cottage in Oregon

4.65 out of 5 average rating, 40 reviews

Quiet Comfortable Cozy Cottage

DrukijloRating, 5 stars11 months ago

Super friendly ! Wonderfully responsive and very kind. We checked in last minute and they were so kind and accommodating! It was a very quiet and peaceful with a really cute and clean kitchen. Would definitely recommend as you are close to the river and it’s such a cute and friendly town !

Flat in Rochelle

4.75 out of 5 average rating, 16 reviews

Stay in our sweet studio

KoreyRating, 5 stars2 months ago

Nice place and great hosts.

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.

5 out of 5 average rating, 15 reviews

Home in Rochelle

Family-Friendly Home in Rochelle

ChristinaRating, 5 starstoday

Carol was so helpful and kind during our stay! I booked to be close to church for the day of our wedding so that the bridal party can get ready. Carol had snacks, face masks, and head wraps for us, it’s the little details that made her such a wonderful host! The place was beautiful and really felt I was at home, enough space to get ready! 10/10

4.86 out of 5 average rating, 69 reviews

Home in Davis Junction

Junction Guest House No PET FEE

KellyRating, 5 stars4 weeks ago

Enjoyed my stay at this comfortable and quiet farmhouse. It was a great place to stay while I was in the area for a dog training event. Telah even let me borrow a dog crate so I had to pack and lug around less equipment. Telah was also very responsive with any questions I had. Will definitely stay here again when in the area.

5 out of 5 average rating, 5 reviews

Guest house in Rockford

Cozy RiverView Home

LindsayRating, 5 stars2 weeks ago

Small but well appointed, will definitely rebook if we are back in the area