Vacation rentals in Oregon

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Top-rated vacation rentals in Oregon

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Guest favourite

Home in Oregon

4.91 out of 5 average rating, 33 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.

May 15 – 22

$165 CAD per night

Guest favourite

Home in La Moille

4.88 out of 5 average rating, 264 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

Dec. 16 – 23

$118 CAD per night

Guest favourite

Cottage in Rockton

4.95 out of 5 average rating, 188 reviews

Country Farm Cottage

Cozy farmhouse Country Cottage on a historic private farm setting. Safe, quiet, peaceful space to relax. Minutes to golfing, hiking, antiques, canoeing, camping, parks, or use as writers retreat. Rockton has great shopping & dining, 20 min to trendy eateries in Beloit WI. Close to local wedding venues Wineries 25 min away May- Nov: orchards cider & donuts Child friendly Visit our Goats Wifi & Roku TVs No Smoking inside No Pets Farm animals and pets on the farm Host lives on same farmstead

Dec. 26 – Jan. 2

$258 CAD per night

Guest favourite

Cabin in Oregon

4.95 out of 5 average rating, 144 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. Pets allowed by adding them to total guest count. $35/night/person/pet after first 2 people. Message Tim about accomodating big groups and events.

Jan. 9 – 16

$352 CAD per night

Guest favourite

Cabin in Oregon

4.97 out of 5 average rating, 131 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.

Feb. 9 – 16

$177 CAD per night

Guest favourite

Farm stay in Cherry Valley

4.97 out of 5 average rating, 273 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.

Aug. 25 – Sep. 1

$150 CAD per night

Guest favourite

Cabin in Dixon

4.94 out of 5 average rating, 125 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

Mar. 13 – 20

$1,092 CAD per night

Guest favourite

Cottage in Franklin Grove

4.94 out of 5 average rating, 140 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!

Mar. 21 – 28

$187 CAD per night

Guest favourite

Cottage in Lena

4.95 out of 5 average rating, 157 reviews

Escape to The Countryside @ Kerlin Schoolhouse!

Welcome to Kerlin Schoolhouse! This Stone Cottage was built in 1870 and was originally a one-room schoolhouse! Kerlin Schoolhouse is located in a quiet, private, peaceful setting in the beautiful countryside. Featuring beautiful views with amazing sunrises, sunsets, windmills, and starry nights! Surrounded by corn fields on all 4 sides. The home features an open concept with loft bedroom & loft-style staircase. Featuring a fireplace, firepit & grill (seasonal), and more.

Jun. 20 – 27

$192 CAD per night

Guest favourite

Home in Oregon

5.0 out of 5 average rating, 32 reviews

Charming Victorian Cottage Near the Rock River

Welcome to Cariad Cottage! Built in 1875 and decorated with treasured antiques, the cottage has all the old-world charm of small-town rural life but with modern amenities and a fully equipped kitchen. Located on a quiet tree-lined street, it’s a short walk into town with multiple restaurants, shops, and a grocery store. A perfect stay includes firing up the grill, having drinks in the screened-in porch, and enjoying the countless recreational opportunities in the area.

Oct. 29 – Nov. 5

$207 CAD per night

Guest favourite

Apartment in Rockford

4.94 out of 5 average rating, 451 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.

Aug. 26 – Sep. 2

$153 CAD per night

Guest favourite

Barn in Freeport

4.97 out of 5 average rating, 509 reviews

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.

Sep. 10 – 17

$155 CAD per night

Vacation rentals for every style

Get the amount of space that is right for you.

Popular amenities for Oregon vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Oregon's top sights

SuperValu5 locals recommend

The Village Bakery5 locals recommend

Conover Square Mall5 locals recommend

Hector's Cocina4 locals recommend

Hazel's Cafe, Coffee & Chocolates7 locals recommend

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

Other great vacation rentals in Oregon

Guest favourite

Guest suite in Oregon

4.97 out of 5 average rating, 33 reviews

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

Nov. 1 – 8

$183 CAD per night

Guest favourite

Home in Oregon

4.97 out of 5 average rating, 36 reviews

Beautiful Home on the Rock River!

Aug. 31 – Sep. 7

$335 CAD per night

Guest favourite

Cottage in Byron

4.94 out of 5 average rating, 49 reviews

2 bedroom cottage with loft. River Frontage...

Feb. 19 – 26

$196 CAD per night

Guest favourite

Cottage in Byron

4.89 out of 5 average rating, 76 reviews

Rock River Views! 2 Bedroom Cabin

Sep. 17 – 24

$217 CAD per night

Guest favourite

Home in Oregon

4.9 out of 5 average rating, 10 reviews

Rock River Getaway!

May 12 – 19

$721 CAD per night

Superhost

Home in Byron

4.9 out of 5 average rating, 10 reviews

Corner house with hot tub hosted by Lucy

Jul. 29 – Aug. 5

$215 CAD per night

Guest favourite

Home in Oregon

4.89 out of 5 average rating, 18 reviews

Cait’s Cottage

Oct. 9 – 16

$154 CAD per night

Superhost

Cabin in Byron

4.87 out of 5 average rating, 39 reviews

2 BR Spacious Comfy Happy Home on the Rock River

Nov. 30 – Dec. 7

$231 CAD per night

Show all

Quick stats about vacation rentals in Oregon

Total rentals
10 properties
Local attractions
Alfano's Pizzeria & Italian Restaurant, SuperValu, and Oregon Park East
Popular amenities
Kitchen, Wifi, and Pool
Wifi availability
10 properties include access to wifi
Total number of reviews
360 reviews
Nightly prices starting at
$124 CAD before taxes and fees

Vacation rentals in Oregon

Top-rated vacation rentals in Oregon

Home in Oregon

Home in La Moille

Cottage in Rockton

Cabin in Oregon

Cabin in Oregon

Farm stay in Cherry Valley

Cabin in Dixon

Cottage in Franklin Grove

Cottage in Lena

Home in Oregon

Apartment in Rockford

Barn in Freeport

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Oregon vacation rentals

Stay near Oregon's top sights

Other great vacation rentals in Oregon

Guest suite in Oregon

Home in Oregon

Cottage in Byron

Cottage in Byron

Home in Oregon

Home in Byron

Home in Oregon

Cabin in Byron

Quick stats about vacation rentals in Oregon

Total rentals

Local attractions

Popular amenities

Wifi availability

Total number of reviews

Nightly prices starting at

Destinations to explore