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Vacation rentals in Oregon

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Top-rated vacation rentals in Oregon

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Home in La Moille

4.89 out of 5 average rating, 300 reviews

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

Home in Dixon

4.96 out of 5 average rating, 123 reviews

Grandma's House, Cozy home in the heart of Dixon!

Escape your busy life and unwind at Grandma's home of hospitality in the quiet and quaint historic town of Dixon, IL! Fishing and boat enthusiasts can take a short 3-block stroll to behold the breathtaking views of the Rock River dam and waterfront. Located only 0.8 miles away is our adorable downtown where you can explore quality retail shops, a charming bookstore, bakeries, a fine art gallery, wine shop, multiple fine dining restaurants. Grandmas House can not be booked for parties/events.

Loft in Monroe

4.99 out of 5 average rating, 151 reviews

Loft 3 - On The Historic Monroe Square

Loft 3 is 40 steps (2 flights of stairs) above the Monroe Square. It's a climb, but the view is totally worth it! Newly remodeled in 2021, and reminiscent of the 1859 character of the building, this space is cute, cozy, and truly one of a kind. Literally a couple steps away from your entryway is Sunrise Donut Cafe, featuring customized donuts and a full menu of excellent coffee items. From there, explore the rest of the Square for food, drinks, and shopping in a quaint Main Street atmosphere.

Cabin in Oregon

4.97 out of 5 average rating, 149 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.

Cabin in Fontana-on-Geneva Lake

4.92 out of 5 average rating, 120 reviews

Exquisite Modern A-frame all WithInnReach

An amazing space that truly caters to the guest experience. We've built this art piece to have our guests immerse themselves in all the amenities, from heated floors to in-ceiling speakers - all whilst losing yourself in the wood burning fireplace. At WithInnReach the attention to detail was paramount - with an emphasis of what we enjoy...amazing food through a well balanced kitchen, beautiful sound through Klipsch speakers and relaxation with floor to ceiling showers...enjoy to the fullest.

Loft in Morrison

4.97 out of 5 average rating, 249 reviews

The Boyd

Completely restored 1892 apartment in the heart of Morrison's national historic district offers Victorian elegance with many modern conveniences. Amenities include a full kitchen, washer/dryer, luxurious queen bed, Roku Smart TV, and high speed wi-fi. The 800 sq ft apartment includes original Doug Fir flooring, 10 ft high ceilings, pocket doors, claw-foot tub, custom cabinets and cherry island. Perched above an art gallery, this is the perfect clean and quiet retreat for work or leisure.

Home in Freeport

4.98 out of 5 average rating, 165 reviews

Willow Lake Getaway Cozy for 2 - or large families

Beautiful 4 bedroom private lakefront home, cozy enough for 2, large enough for family gatherings for holiday/wk end escape/vacations. Hot tub for cool eves October-April. Extensive private decks with BBQ, outdoor dining & circular daybed with umbrella. 2 docks, 2 SUP boards, paddle boat, 2 kayaks, pingpong table, books and board games. 2 Master Suites with smart tv with private balcony & seating area. fire pit located next to 1st dock. Couples get a 10% discount, message me for details.

Farm stay in Cherry Valley

4.97 out of 5 average rating, 330 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.

Place to stay in Brodhead

4.98 out of 5 average rating, 124 reviews

Historic Randall Schoolhouse

You'll love this beautifully redone Historic One-room Schoolhouse. Situated on the edge of the Driftless area 5 miles from the Sugar River Trailhead. An easy 30 minutes to Monroe, Beloit & Janesville and just an hour outside Madison. Relax in comfort with all new appliances including a full kitchen, washer/dryer, dishwasher and fireplace. Fenced yard. Just a mile down the road from a working homestead where you can milk a cow, pet a goat, harvest fresh produce and eggs and so much more.

Cabin in Dixon

4.93 out of 5 average rating, 163 reviews

MASSIVE 5 BED WATERFRONT COZY CABIN GETAWAY!

ROCK ISLAND RESORT!! RIVERFRONT PARADISE CLOSE TO HOME!! ON 12 ACRES OF LAND!!! 4200sqft 2 Story Cabin w/open floorpan 5 Bedroom 3.5 Bath Sleeps 26 Wifi 50in Flat Screen in each room (Dish TV) AMENITIES: -Trampoline -2 Power Wheels (kids) -Soccer Field -Regulation Volleyball Net -Fire Pits -Wrap around deck -Gas Grill -4 kayaks / Three 16ft 3 person canoes -Air Hockey -Pool Table -Foosball Table -Full size ping pong table -Mini Arcade -Fishing Poles PRICELESS RIVERFRONT VIEWS

Cottage in Franklin Grove

4.94 out of 5 average rating, 164 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!

Rental unit in Rockford

4.94 out of 5 average rating, 515 reviews

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.

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Oregon vacation rentals

Free parking on premises

Air conditioning

Stay near Oregon's top sights

Lowden State Park10 locals recommend

White Pelican Canoe & Kayak Rental -- Oregon, IL8 locals recommend

Hazel's Cafe, Coffee & Chocolates7 locals recommend

The Village Bakery5 locals recommend

SuperValu5 locals recommend

Conover Square Mall5 locals recommend

Other great vacation rentals in Oregon

Home in Rochelle

4.98 out of 5 average rating, 46 reviews

Julie's House on Main

Home in Rockford

5 out of 5 average rating, 62 reviews

NEW! Adults Only Riverfront home with "Red Room"

Cottage in Byron

4.95 out of 5 average rating, 62 reviews

2 bedroom cottage with loft. River Frontage...

Cabin in Brodhead

4.89 out of 5 average rating, 71 reviews

Cozy Cabin on Decatur Lake

Rental unit in Sterling

4.89 out of 5 average rating, 55 reviews

Downtown Red Door Secret

Home in Oregon

4.92 out of 5 average rating, 13 reviews

Gorgeous Sprawling Acreage w/ Stunning Views

Cabin in Oregon

4.85 out of 5 average rating, 81 reviews

Cozy Log Cabin in the Woods: Pine Creek Escape

Guesthouse in Byron

4.97 out of 5 average rating, 38 reviews

Duplex Overlooking Rock River

Quick stats about vacation rentals in Oregon

Total rentals
10 properties
Nightly prices starting at
$70 before taxes and fees
Total number of reviews
480 reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
10 properties include access to wifi

Frequently Asked Questions

Are there family-friendly vacation rentals in Oregon?
Oregon has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in house rentals in Oregon?
Experience the best of Oregon with our house rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Oregon have a kitchen?
Absolutely! We offer over 10 house rentals with a kitchen in Oregon. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Oregon have wifi?
Absolutely! We offer over 10 house rentals with wifi in Oregon. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Oregon?
Yes! Work meets play with ease at over 10 vacation rentals in Oregon featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Oregon have free parking?
Absolutely! We offer over 10 house rentals with free parking in Oregon. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore