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Smoking friendly vacation rentals in Illinois

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Top-rated smoking friendly rentals in Illinois

Guests agree: these smoking friendly rentals are highly rated for location, cleanliness, and more.

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Top guest favorite

A doorway is viewed from inside, featuring a decorative welcome mat. The door opens to a private wooden deck, which is partially visible. Natural light filters in through the glass, highlighting the contrasting textures of the mat and the wooden deck.

Apartment in Savanna

4.95 out of 5 average rating, 131 reviews

RiverView Lux: 420 Damage Control, private deck

420 Friendly, this newly remodeled spacious apartment is conveniently located on the Mississippi River side of Main St in the heart of downtown Savanna. You have all the access with none of the noise. Stunning river views from your own private deck. Whether you are looking for a romantic weekend, outdoor adventures or scenic curvy roads to ride we have you covered. Comfy couches, King sized bed, clawfoot tub everything you need to enhance your comfort while you stay with us at Damage Control.

Top guest favorite

An inviting outdoor space is illuminated by string lights, creating a cozy atmosphere. A large dining table is surrounded by comfortable chairs, with colorful cushions adding a pop of color. Lush foliage and a fenced yard provide a private setting for relaxation.

Apartment in McHenry

5 out of 5 average rating, 128 reviews

Walk to downtown McHenry. Heart of the Fox River

NO PETS Entire 2nd. floor. 1 block away from downtown, Fox River Riverwalk & Pokémon Gym. Full stocked kitchen, books, games, toys & extra amenities to make your stay beyond relaxing. 4:20 allowed in backyard & not in view of under the age of 21. Private smoking area in front too. Minutes away from 2 State Parks, 1 with free boat/kayak launch. Several marinas, boat rental, golf courses & huge variety of entertainment. Look at Bettye's Guidebook for more information & nearby entertainment.

A serene landscape featuring a solitary tree reflected in calm water. The setting sun casts gentle hues of pink and purple across the sky, while the moon is visible, adding to the tranquil ambiance of the Illinois River.

Home in Pittsfield

4.85 out of 5 average rating, 239 reviews

Florence Guest House

ONE DAY ADVANCE NOTICE BOOKING! This 1,200 sq. ft. PRIVATE BOOK is a 175 year old building that Abe Lincoln stayed in. Central A/C, Forced air heat, Two decks (one overlooking the Illinois River), burn pit, outside grill, fully equipped kitchen, screened in porch, ample parking, access to the Illinois River/ boat ramp near, tie up on Our Private Lots! NOTE: RECENTLY HAD Guests' wanting to "JUST GET AWAY" for A Time!!! PRIVATE TIME ALONE, Guaranteed!!! NEW KEURIG; BRING YOUR K-CUPS!!!***

A modern kitchen countertop displays a sleek air fryer beside a stainless steel toaster. The appliances are set against a backdrop of white tile and dark cabinetry, with gold accents on the hardware adding a touch of elegance.

Home in Chicago

4.96 out of 5 average rating, 174 reviews

Chicago River House -BBQ Oasis now open!

Close to must see Chicago restaurants and nightlife, yet nestled in nature! This 1937 Print Shop is seated between the Chicago River & Forest Preserves, with trails & river walks, 3 miles to the beach, near Lake Shore Drive & 90/94, nearby Lincoln Square , Andersonville, and seasonal waterfalls, brunch nearby. This 2-bed, 2-bath home one level. 5star Chef's kitchen 9’ x 15’ HD projector, comfy beds, double shower head shower room, near nature. Relax on our private patio and glowing furniture

Top guest favorite

Two deer, one adult and one fawn, are seen standing in a grassy area beside a wooden fence. The lush greenery surrounding them emphasizes their natural habitat, while the soft sunlight highlights the gentle features of the deer.

Guesthouse in Jerseyville

4.97 out of 5 average rating, 139 reviews

Cozy cabin on farm near Jerseyville and Grafton IL

No cleaning fees! Relax in this cozy cabin on a 30 acre farm w/beautiful views & peaceful surroundings. Near shopping, wineries, nightlife, hunting & fishing. Abundant wildlife & farm animals-horses, cows, chickens, goats, sheep, geese. Two bedrooms (one in a spacious loft) with a queen sofa sleeper in the living room. Full kitchen w/dish washer. Fireplace & cathedral ceilings in living room. Full bath w/shower. Covered front porch. Screen porch off living area w/outdoor seating. Fire pit.

A spacious backyard features a wooden deck with a pink picnic table and two blue chairs. Flower beds and a fire pit are visible among the greenery. A grill and a small stone area are also included, surrounded by a privacy fence.

Guest suite in Chicago

4.9 out of 5 average rating, 110 reviews

1 bed apartment + futon room bridgeport

Located at the geographic center of Chicago! Plenty of free street parking. Very safe and ~10 min walk to the 35th Orange line and 3 blocks from the Archer bus, both go directly downtown within minutes. Brand new lower level construction unit. Comfortable spacious rooms to relax in. Closet in both rooms for your use while here. The apartment has a separate entrance, bathroom, kitchen, dining space. Enjoy your own private space in Chicago with a back patio, grill, and laundry.

A sheltered pavilion provides a view of a serene lake, framed by lush green trees. Several picnic tables are arranged on the grassy area, and a kayak is seen gliding across the water in the distance. The space appears inviting for outdoor gatherings.

Apartment in Lake Zurich

4.94 out of 5 average rating, 144 reviews

Take A Pebble Apartments Apt#4 (1 Bedroom)

Come stay at Take a Pebble apartments located in downtown Lake Zurich, Illinois. Only a 2 minute walk to our lake. Breakfast, Fast Food, Fine Italian/Pizza Restaurant & a few Bars all in our downtown area. Parking is at a public lot just 90 seconds from the entrance. Below your room is Offbeat Music & LP Records. Take a few records back home with you or better yet a Drum Set!!! Take A Pebble Properties was named after a song by the great band Emerson Lake & Palmer.

A cozy sitting area features a plush sofa adorned with a colorful blanket, surrounded by large windows that provide views of the forest. A ceiling fan hangs above, while a chair and lamp complete the inviting space.

Place to stay in Cobden

4.94 out of 5 average rating, 312 reviews

Eva’s Roost - Retreat Cabin

Eva’s Roost is located at Center For Lost Arts near Cobden, Illinois. Uniquely crafted rustic, zen-style cottage, designed to be close to the earth & nature. Extensive, curtainless windows facing the forest & pond allow for private views: sunrise, moonrise, forest & wildlife. Yoga mat, guitar & some art supplies. Personal outdoor space with firepit & comfy adirondack chairs. Entrance to wandering trails right outside your back door. Perfect place to retreat and renew.

Top guest favorite

Guest suite in Chicago

4.95 out of 5 average rating, 164 reviews

Cozy Home Living, Dogs, Kids, Free Parking, 420 OK

Private entrance apartment on the 2nd floor of this historic bungalow. Free street parking! Medicinal & recreational smokers permitted... outdoor ONLY. This comfortably cozy quiet get-away is nestled in NW Portage Park in a family neighborhood. Dog and kids park nearby. Fenced yard for Fido. Backyard patio w/ BBQ grill. High-speed internet. Front porch swing Easy access to buses & Jefferson Park Transit train station to Downtown & Museum Campus NO PARTIES

An outdoor deck showcases a round table surrounded by four chairs with cushions. An additional chair is positioned nearby. A patterned rug lies beneath the table, providing a cozy area for relaxation. Distant green grass and trees can be seen in the background.

Home in Carthage

4.93 out of 5 average rating, 138 reviews

Nice 2 bedroom home w/attached garage & deck.

Nearby attractions in Carthage include historic Carthage Jail & Kibbe Museum, historical Carthage courthouse, public swimming pool & golf course, several public parks & library, shopping, restaurants, and the Legacy Theater. Many recreational activities & special events year round. Located just minutes from the interstate. 16 miles from Nauvoo, IL. 15 miles from Keokuk, IA. 27 miles from Macomb, IL. 43 miles from Quincy, IL. 59 miles from Hannibal, MO.

Cabin in Oregon

4.96 out of 5 average rating, 182 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.

A bright living room is illuminated by natural light from large windows. A white sofa is paired with two orange chairs, complemented by vibrant cushions. A coffee table with a striped design sits centrally, surrounded by decorative plants and artwork on the walls.

Apartment in Chicago

4.95 out of 5 average rating, 700 reviews

Best in Chicago, private, amazing garden space

We offer the highest standards of cleanliness. Excellent workspace with fast wifi and beautiful outdoor deck and garden space to relax. The most popular Airbnb in Illinois (Buzzfeed, Aug. 2017). After 12 years hosting we still enjoy making our space a special place…as one reviewer commented, "The pictures don't really do justice to how beautiful the apartment is. I will miss having my morning coffee while overlooking the tranquil garden."

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Popular amenities for Illinois smoking friendly rentals

Free parking on premises

Air conditioning

Smoking friendly apartment rentals

A spacious living room features a gray sectional sofa and a round area rug, complementing a stylish coffee table at the center. Natural light filters through sheer curtains, while a piece of abstract wall art adds a pop of color. A potted plant adds a touch of greenery.

Apartment in Thornton

4.86 out of 5 average rating, 22 reviews

Your quiet south suburban oasis

A charming house stands amid a lush garden, featuring a variety of plants and shrubbery. Straw and natural materials create beds for growing vegetables. Sunlight filters through the trees, illuminating the scene, while the structure showcases a welcoming porch and a pitched roof.

Apartment in Chicago

4.84 out of 5 average rating, 133 reviews

Studio Apartment in Nature Sancturary

A spacious living area features a sectional sofa with patterned cushions, a coffee table adorned with magazines, and a foosball table nearby. The kitchen space is visible, showcasing modern appliances and stylish cabinets, while a feature wall adds a unique touch to the room.

Apartment in Chicago

4.79 out of 5 average rating, 33 reviews

Hypebeast Experience

A cozy living space features a mix of seating options, including a brown leather armchair, two fabric sofas, and an ottoman. A round coffee table sits in the center, while a floor lamp provides soft illumination. Nearby, a mounted television is visible through a window.

Apartment in Downers Grove

4.74 out of 5 average rating, 73 reviews

Pet friendly private studio apartment in a home

A bright living area features large windows dressed with sheer curtains, allowing natural light to fill the space. A modern coffee table is centered on a polished hardwood floor. Comfortable seating includes a gray sofa and two armchairs, complemented by a TV mounted on the wall above a white fireplace.

Apartment in Chicago

4.95 out of 5 average rating, 111 reviews

420 at Cheltenham 4BR

An outdoor lounge area features a rectangular table with a central firepit, surrounded by comfortable seating with purple cushions. The backdrop showcases the Chicago skyline against a clear blue sky, adding a scenic view to this rooftop retreat.

Apartment in Chicago

4.83 out of 5 average rating, 54 reviews

Price Drop Now Through July 4th Weekend!

The spacious bedroom features a large queen size bed with a striped blanket. A mounted TV is positioned on the wall, displaying various streaming options. Light-colored wooden floors enhance the room's brightness, while an additional room with a bed is visible through open double doors.

Apartment in Rockford

5 out of 5 average rating, 5 reviews

Charming 2 bedroom Apartment

A comfortable living area features a spacious gray sectional sofa adorned with decorative pillows. A small coffee table sits atop a colorful area rug, and artwork is displayed on the wall. Natural light enhances the calm atmosphere of the space.

Apartment in Calumet City

4.9 out of 5 average rating, 30 reviews

Welcome to True Blue.

Smoking friendly house rentals

The exterior of the home is showcased, featuring a light-colored facade complemented by neatly trimmed shrubs. Stairs lead up to a welcoming entrance, while a well-kept lawn and mature trees provide shade. The roofline is distinctive, adding character to the overall appearance.

Home in Oak Park

4.94 out of 5 average rating, 17 reviews

Spacious Designer Oasis: Game Room - Yard - Garage

A charming cottage exterior is presented, featuring gray siding and a neatly maintained yard. The building shows multiple large windows that enhance natural light. A stone pathway leads to the entrance, while a detached garage is visible alongside the grassy area.

Home in Wonder Lake

4.9 out of 5 average rating, 10 reviews

Just Off The Lake Comfort

A charming three-story house features a distinctive metal roof and is surrounded by trees. A large porch extends along the front, providing shaded areas. Access to the serene lake is visible nearby, contributing to the peaceful setting.

Home in Creal Springs

4.89 out of 5 average rating, 56 reviews

Lake of Egypt Paradise Lodge

A spacious master bedroom features a large bed adorned with a gray quilt. Natural light filters through the sheer curtains on two windows, illuminating the warm wooden floor. Nightstands are positioned beside the bed, and a bench is situated against the wall.

Home in Shawneetown

4.95 out of 5 average rating, 38 reviews

Blackberry Hill—Welcome Hunters, Hikers, Bikers

An aerial view captures a spacious lakeside property surrounded by lush trees. A private slip dock extends over the calm water, accommodating boat access. The elegant home features large windows, blending with the natural landscape, creating a serene lakeside setting.

Home in Creal Springs

5 out of 5 average rating, 9 reviews

Waterfront- Egypt Shores Luxury Retreat

A spacious living area features a modern television mounted on a light-colored wall, flanked by a comfortable sofa set. A neutral coffee table sits centrally, while soft natural light enhances the inviting atmosphere through large windows. A dining area is visible in the background.

Home in Romeoville

4.93 out of 5 average rating, 15 reviews

Rejuvenate: 4BR, fenced yard

The indoor pool area features a large swimming pool with clear blue water, surrounded by wooden beams and glass panels that create a bright atmosphere. A hot tub is located nearby, and seating is arranged along the pool's edge, providing a relaxing space for guests.

4.9 out of 5 average rating, 51 reviews

Pearl Street Pool House

A covered porch features a round table surrounded by chairs and two spacious Adirondack chairs. Soft lighting is provided by string lights and a lantern that rests on the table, creating a cozy setting against the backdrop of a twilight sky.

4.85 out of 5 average rating, 13 reviews

Shawnee Forest Vacation Lodge

Smoking friendly condo rentals

A spacious living area features a modern sectional sofa in warm tones, positioned around a circular coffee table. Large windows allow natural light to fill the room, showcasing a view of the outdoors. A neutral area rug anchors the seating arrangement, enhancing the home’s contemporary design.

Private room in Chicago

4.88 out of 5 average rating, 307 reviews

Private BR in Condo close to Chicago Dwtwn!

Top guest favorite

Condo in Chicago

5 out of 5 average rating, 59 reviews

Where you want to BE! Stylish, Comfy, Luxe

A well-lit hallway features smooth wooden flooring and a neutral area rug. Framed art pieces adorn the walls, while a stylish console table holds decorative items. Potted plants and a modern chair create a welcoming atmosphere at the far end of the corridor.

Condo in Chicago

4.57 out of 5 average rating, 14 reviews

Urban Oasis: South Shore Chicago

A long hallway is lined with chalkboard-painted walls, showcasing colorful drawings and notes. Light is provided by ceiling fans and bright fixtures, leading towards an entryway with a glimpse of furniture and natural light coming from an open door.

Private room in Chicago

4.86 out of 5 average rating, 84 reviews

Beautiful condo close to the beach

A private balcony is presented with cozy seating and potted plants along the railing. A view of the surrounding area is visible, framed by brick columns and a decorative rug underfoot. The sky displays soft, diffused clouds that enhance the peaceful atmosphere.

Condo in Chicago

4.96 out of 5 average rating, 52 reviews

Beautiful Condo in North Kenwood with Parking

A spacious living area features a leather sectional couch arranged around a round coffee table. Large windows allow natural light to fill the room, highlighting the hardwood floors and elegant chandeliers above. A plush area rug contrasts with the dark wood, creating a cozy atmosphere.

Private room in Chicago

4.89 out of 5 average rating, 271 reviews

Private BR in Chicago - Dwntwn & Fulton Mkt close

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