Holiday rentals in Shorewood

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Top-rated holiday rentals in Shorewood

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Guest favourite
A spacious dining area features a dark wooden table accompanied by matching chairs and a bench. A vibrant orchid in a blue pot adds a touch of color. In the background, a living space is visible, offering comfortable seating and bright natural light.
Flat in Cathedral Area
4.96 out of 5 average rating, 190 reviews

*The Historic Hideaway*/King Bed/Remodeled/Wi-Fi

Our Spacious apartment is located on Plainfield Road, minutes away from 1-80 & 1-55. Near: Rialto Theatre, Haley Mansion, Jacob Henry Mansion, Joliet Union Station, College of St. Francis, Joliet Junior College, Slammers Minor League Baseball and St. Joe's Hospital. Minutes away from: Chicagoland Speedway, Hollywood Casino, Lewis University and Silver Cross Hospital. 30 minutes SW of Chicago. 3 bedroom (1 King, 2 Queens. 1 queen sleeper sofa) Rooms are tastefully decorated with unique artwork.

Guest favourite
The exterior of a single-story home is framed by lush green grass and dark mulch landscaping. A welcoming pathway leads to the front door, adorned with a seasonal wreath. A large tree provides shade, and a white fence marks the boundary of the yard.
Home in Naperville
4.87 out of 5 average rating, 162 reviews

Dog Friendly Cozy North Naperville 3 BED/2 BA Home

Welcome to the Naperville Nest! Rare North Naperville opportunity to find a home suited for the whole family! Pets are more than welcome to enjoy the 1/2 acre fully fenced in yard. This is a a fully updated home minutes from Downtown Naperville, I-88 and many more exciting destinations in the Western Suburbs. You will feel at home whether you're inside or outside...each bedroom has it's own TV and the outdoor living includes natural gas firepit & grill/dining table...this home has it all!

Guest favourite
A cozy bedroom features a comfortable bed with a quilted cover and decorative pillows. A colorful textile art piece depicting Route 66 is displayed on the wall. A side table with a lamp adds to the charm, complemented by a vintage photograph hanging above.
Home in Lockport
4.96 out of 5 average rating, 162 reviews

Lockports Famous Hideaway ~ 2bdrm Guest House Flat

A history buff’s dream filled with antiques & artifacts relating to Chicago, Joliet, Lockport, the I & M Canal & "Route 66"! *Note: Pricing is based on "Double Occupancy". Extra charges per person apply after 2 guests. Can accommodate up to 6 guests. Family & Business Friendly. The entire upstairs 1,500 sq ft vintage 2-bedroom house apartment is all your own space. The flat is NOT shared with other guests/host. Private-entrance/self-check-in. Have a 'historic' stay at the "Hideaway"!

Guest favourite
A spacious bedroom features a king-size bed adorned with a colorful quilt and accent pillows. A wall mural of large ferns creates a vibrant backdrop. A full-size futon is positioned alongside, with a lamp and window allowing natural light to brighten the area.
Home in Joliet
4.92 out of 5 average rating, 226 reviews

The Garden House - Murals and more

Our garden-themed house🌿 located on busy Plainfield Road is minutes away from 1-80 & 1-55. Near: Rialto Theatre, Haley Mansion, Jacob Henry Mansion, Joliet Union Station, College of St. Francis, Joliet Junior College, Slammers Minor League Baseball & St. Joe's Hospital. Minutes from: Chicagoland Speedway, Hollywood Casino, Lewis University & Silver Cross Hospital. 30 min. SW of Chicago. 🏡Entire house: 2 Bdr (2 Bd & 1 Futon), Bathroom (new shower), Living Room, Kitchen, Front Deck

Guest favourite
A spacious living area features a corner sectional sofa with soft cushioning and a cozy throw. Large windows provide natural light and city views. A simple coffee table sits in front, with light-colored carpet underfoot, enhancing the comfortable atmosphere.
Flat in Aurora
4.98 out of 5 average rating, 227 reviews

Penthouse In The Historic Hobbs

Experience luxury and historic charm at the Penthouse in the Historic Hobbs. Built in 1892, and restored in 2023, this new one bedroom corner unit offers a panoramic view of the Aurora skyline. Cook a delicious meal in the fully stocked kitchen. Dine at the bespoke table in the window bay under the iconic onion dome. Relax on the cozy sofa and enjoy a movie on the big screen TV. Rest in the plush king-sized bed. This urban retreat is near coffee, shopping, art and entertainment.

Top guest favourite
A charming cottage exterior is framed by lush green trees and manicured shrubs. The white siding and dark shutters provide a classic contrast. A welcoming front door is situated at the center, with a path leading to a single-car garage on the right.
Home in Morris
4.92 out of 5 average rating, 48 reviews

Chapin Cottage

Chapin Cottage is a peaceful two-bedroom single-family home centrally located on the east side of Morris. Extremely walkable to all Morris has to offer, it is only six blocks from hiking and biking on the historic I&M canal, and boating, fishing, and kayaking on the Illinois River. Head west six blocks and enjoy shopping, delicious and unique dining, and fun festivals and Cruise Nights in beautiful downtown Morris. Let this peaceful cottage be your home away from home here in Morris.

Guest favourite
A spacious living room features a large sectional sofa and two blue upholstered chairs, arranged around a black coffee table on a light area rug. A flat-screen TV is mounted on the wall, flanked by shelves with decorative items. Natural light enters through large windows with sheer curtains.
Home in Oswego
4.91 out of 5 average rating, 148 reviews

Cozy 4-bedroom ranch - minutes from everything

Relax and have fun with the whole family at this peaceful place to stay. It is located within walking distance from US Route 34 in the middle of shopping centers such as Meijer, Jewels, Target, Walmart, great restaurants, bars, entertainment, hair and nail salons, gas stations, etc. There are 5 beds (1 king and 4 queens plus a queen-size air mattress and a twin pull-out bed) and 3 couches waiting for their guests. The house is cleaned and sanitized before every reservation.

Superhost
The exterior of the home features a brick facade with a steeply pitched roof and well-maintained landscaping. A set of steps leads to the front door, flanked by neatly trimmed bushes and a variety of greenery. Large trees offer shade in the front yard.
Home in Joliet
4.74 out of 5 average rating, 19 reviews

Cozy Cottage with Home Theatre in Joliet

Unique home because the top is totally how we bought the home everything is original from 1920's. Now the basement we renovated hence it feels like completely two different spaces. In this listing you are getting two full kitchens, 2 living rooms, 3 bedrooms and 2 bathrooms. Since this is a 1920s home there is no central air conditioning. Upstairs, there are windows units in the bedrooms that keep those rooms very cool. Downstairs, there are wall units.

Top guest favourite
A bright kitchen is furnished with white cabinetry and a light-colored countertop. Modern appliances, including a microwave and an oven, are positioned for convenience. Natural light enters through the window, complemented by decorative elements on the wall and counter for a welcoming touch.
Home in Ottawa
4.94 out of 5 average rating, 189 reviews

"You're invited" Suitcase Required

The whole group will enjoy easy access to everything from this centrally located place. Head to our many state parks, take a boat ride down the Illinois River, be adventurous and skydive at Skydive Chicago and the list goes on. This two-bedroom 1 bath house welcomes you with all the amenities to feel right at home. Sleeps 3 adults comfortably. (1-Queen Bed and 1 full size bed) It has a fully stocked kitchen. washer/dryer and outdoor seating/dining.

Guest favourite
The living area features a comfortable seating arrangement with a sofa and two armchairs. A round coffee table sits in the center on a patterned area rug. Soft lighting enhances the neutral wall tones, while a decorative plant adds a touch of greenery.
Flat in Warrenville
4.93 out of 5 average rating, 100 reviews

“The remote retreat”

We have a cozy one bedroom apartment that is available on the top floor of the home and has its own independent and separate entrance! Comes with free parking on premises; recently renovated; neighborhood is safe and quiet. Shopping center with grocery store, laundry mat and restaurant is available within walking distance! We are only 5 minutes from the expressway I-88 and 10 minutes from Naperville and the outlet mall in Aurora!

Guest favourite
Guest suite in Joliet
4.96 out of 5 average rating, 50 reviews

Home Sweet Home

Quiet, Fully Finished Basement Apartment—Ideal for Business Travel - 2 bedrooms with full-size beds & 32" smart TVs - Living room with 55" smart TV (Hulu/Netflix) - Full kitchen for meal prep or extended stays - Bathroom with soaker tub & shower - Private back patio & front porch - No guests under 16 - Quiet hours & respectful use of shared spaces - Home uses well/septic—do not flush hygiene products

Top guest favourite
A tranquil lake scene is depicted, featuring autumnal trees reflecting vibrant hues of yellow, orange, and red in still water. The grassy shoreline enhances the serene environment, while neighboring greenery contributes to the picturesque landscape.
Guest suite in Naperville
4.96 out of 5 average rating, 501 reviews

Cozy Lakeview Studio with Private Access

Enjoy luxury and comfort in this cozy lakefront studio with a private entrance, attached to a home where the friendly hosts reside. The studio offers a plush queen bed, a kitchenette with a mini fridge, microwave, induction cooktop, and a full bathroom. Located in one of Naperville’s safest neighborhoods, it’s just moments from cafes, restaurants, markets, and a biking trail, with easy access to I-88.

Popular amenities for Shorewood holiday rentals

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  2. United States
  3. Illinois
  4. Will County
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