Holiday rentals in Essex

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Top-rated holiday rentals in Essex

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Top guest favourite
The cabin is nestled among tall trees, featuring warm lighting that highlights the rustic wooden structure. A spacious deck extends from the cabin, with a hammock positioned between trees, inviting relaxation amidst nature. Smoke gently rises from the chimney, suggesting a cozy atmosphere inside.
Cabin in Oregon
4.96 out of 5 average rating, 197 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. $33/night per person or pet after first 2 people. Message Tim about accomodating larger groups and events. Closed for winter November through March.

Superhost
A comfortable living area features a spacious sofa with neutral-toned cushions. A glass coffee table sits atop a decorative rug, and wooden shelves display books. Natural light enters through window treatments, complemented by patterned curtains and a floor lamp.
Cottage in Wilmington
4.92 out of 5 average rating, 170 reviews

Get Your Kicks in Our Cozy Cottage Near Route 66

Enjoy the comforts of home when you have to be away. Our fully furnished cottage is located 4 miles from Rt 53 / Historic Rt 66 & just blocks from the Kankakee River. Just 5 minutes to "downtown" Wilmington featuring restaurants, a wine bar, a local brewery, and multiple antique stores. ✧ Easy access to everything that Joliet has to offer just 20 miles away, including the Autobahn and Route 66 Raceway / Chicagoland Speedway. ✧ 7 miles to easily access I55 for a quick ride into Chicago.

Superhost
A fully equipped kitchen features wooden cabinetry and a black refrigerator. Appliances include a gas stove, microwave, and toaster oven. The countertop is complemented by a dishwasher. A small dining area with a wooden table and place settings is visible nearby.
Flat in Bourbonnais
4.87 out of 5 average rating, 415 reviews

Lyle and Taylor present-Spacious Private Apt -

Beautiful spacious apartment perfect for long term work assignments or travelers who want all the comforts of home. Sleeps up to 5; King, Queen + sofa Amenities abound: ~FREE WiFi ~2 smart TVs w/HBO, SHOWTIME, Cinemax, 144 cable channels, Netflix ready (with your account) ~Full kitchen with fridge/gas stove/dishwasher/microwave/toaster oven/Keurig ~FREE washer & dryer with basic supplies ~Bathroom w/shower/tub combo ~Non-smoking ~Complimentary weekly cleaning/linen laundry for extended stays

Guest favourite
A welcoming porch area features a green and beige exterior with a door leading into the loft. Decorative pumpkins and flowers are arranged on hay bales, complemented by a rustic chair. Surrounding trees provide a natural backdrop.
Flat in Chebanse
4.94 out of 5 average rating, 717 reviews

Cathy's Little Farm Loft

Cathy's Little Farm loft is a 500 sq ft apartment inside a storage barn on a wooded country acre. Fully appointed two story space offers peace and quiet. It is located close to I57, Walmart, Community College, Airport, Fair Grounds, National Guard Training Center, 15 minutes from Olivet, 60 miles south of Chicago. King size bed and twin size sofa sleeper upstairs, full size sleeper sofa in living room. Well equipped full size kitchen and laundry. Large lawn, gardens, and chickens to enjoy.

Guest favourite
Flat in Kankakee
4.94 out of 5 average rating, 189 reviews

King Bed • Luxury Boho Studio • City Chic Haven

✤City Chic Haven✤ is a luxury studio in downtown Kankakee, steps from the train station, taverns, and walkable attractions. Enjoy a cozy king bed, fast Wi-Fi, free coffee/tea bar, stocked kitchen, & 55” smart TV for a relaxing or work friendly stay. ✶ Across the street from the Kankakee train station ✶ Walkable to local cafes, axe throwing & taverns ✶ 0.3 Miles to St. Mary's Hospital ✶ 1.3 Miles to Riverside Medical Center ✶ 2.9 Miles to Olivet Nazarene University ✶ 55 Miles to Midway Airport

Guest favourite
Home in Mazon
4.93 out of 5 average rating, 14 reviews

Cozy Little Small-Town Home

This charming two-bedroom home provides a comfortable, convenient stay for families or traveling professionals. The home has two bedrooms, each with comfortable queen mattresses and quality linens. The fully equipped kitchen, in-unit washer and dryer, and smartlocks make for a seamless stay. Close to Dresden (18 miles), Braidwood (12 miles) and LaSalle (14 miles), the home is central for any outage and flexible leasing is available to outage workers and traveling healthcare professionals.

Top guest favourite
A serene bedroom is highlighted by a large tufted bed with decorative pillows and a warm throw. Natural light filters through elegant curtains at the windows. A stylish chandelier and a decorative mirror above a contemporary dresser enhance the chic ambiance, complemented by soft wall colors and textured accents.
Flat in Fairbury
5 out of 5 average rating, 428 reviews

Chic Retreat Small Town Charm, City Sophistication

The ultimate escape, at Wells on Main Guesthouse & Gatherings where small-town charm meets big-city sophistication. Whether it’s a romantic getaway, girls’ weekend, or just time to recharge, our elegant retreat has you covered. Couples can cozy up in dreamy spaces and create lasting memories. Gather your best friends for laughter, wine, and chic relaxation in a stylish setting. With local charm and upscale comfort, every moment feels magical. Book a week long stay and receive 40% off ❤️

Top guest favourite
Guest suite in Kankakee
4.95 out of 5 average rating, 42 reviews

Private Riverfront Oasis Guest Studio

Welcome to your private river front retreat! This spacious, fully equipped, private studio guest suite is tucked away on the beautiful Kankakee River (with a view!). Located less than 5 miles from I-57, this hidden gem offers convenience of location as well as peaceful beauty. Relax on the porch, take a dip in the river or chill in the hot tub to pass the time. The guest suite is attached to the main house but boasts its own private keypad entry and a completely private stay.

Top guest favourite
Flat in Wilmington
4.9 out of 5 average rating, 109 reviews

Ground Floor Downtown Wilmington Studio Route 66

Located in downtown Wilmington, IL, Studio 66 is within walking distance to restaurants, bars, and the scenic Kankakee River. Whether you’re traveling Route 66, visiting family, or here for work, this spacious studio offers a convenient place to stay right off the historic “Mother Road.” Need an extra bed? We have an optional 31" x 75" rollaway cot (ideal for a child/single adult). It is kept locked away to maximize space for couples; see 'Other things to note' to request access.

Top guest favourite
The barn-style property is shown with a two-story deck leading to the entrance. The red exterior contrasts with white railings and a gray metal roof, surrounded by lush greenery. A paved area in front provides ample space, while cornfields are visible in the background.
Barn in Rensselaer
4.99 out of 5 average rating, 364 reviews

The Loft at Virgie

You don't have to be born in a barn to vacation in one. Trade in the city for millions of stars in the night sky! As you enter thru the French doors you will be greeted by an open concept room decorated with a barn/industrial motif. Knotty pine car-siding and galvanized steel, wood floors along with a reclining leather couch and love seat fill the room A full kitchen with granite counter tops await you. There is plenty of natural lighting for the evenings.

Guest favourite
An inviting living room is presented with a comfortable sofa and an armchair, accented by decorative elements on the walls. A wooden TV stand holds a television, while natural light enters through a front door and large windows, enhancing the cozy atmosphere.
Home in Wilmington
4.92 out of 5 average rating, 108 reviews

Cheerful 2 bedroom home near Rt. 66

Soak up the hometown charm with a relaxing and tranquil stay in historic Wilmington near the Kankakee River. You won't be living in a van down on the river during this stay. You'll enjoy a warm, cozy home that's near shopping, flavorful restaurants and picturesque sunsets on the Kankakee River. This two bedroom home can accommodate up to six people. The kitchen and living room feature an open concept for more intimate or a night with close friends.

Top guest favourite
Home in Morris
4.97 out of 5 average rating, 29 reviews

Charming Canal-Port Cottage-Come &Relax in nature

Escape to our **Cozy Canal Port Cottage**, where nature meets relaxation. Nestled on the historic I&M Canal and minutes from downtown Morris, this charming 2-bedroom retreat offers peace, comfort, and wildlife views. Enjoy a fully equipped kitchen, grilling area, comfy beds, and a serene setting near Starved Rock and Buffalo Rock. Perfect for couples or small families to unwind, explore, and recharge. We can not wait for you to stay with us.

Popular amenities for Essex holiday rentals

  1. Airbnb
  2. United States
  3. Illinois
  4. Kankakee County
  5. Essex