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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 hot tub is positioned on a private deck, featuring bubbling water and a clear view of the Mississippi River in the background. A wooden railing surrounds the area, complemented by blue drapes. Lush greenery is visible along the riverbank.

Apartment in Savanna

4.95 out of 5 average rating, 133 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.

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, 183 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.

Top guest favorite

A two-story house is presented with a welcoming blue front door and bright flower pots lining the entrance. The property is surrounded by neatly maintained grass and pathways, with trees and shrubs adding greenery to the inviting façade.

Apartment in McHenry

5 out of 5 average rating, 130 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 private outdoor patio is surrounded by wooden fencing, featuring a glowing sofa and two chairs placed on a patterned rug. A small table holds a plant, while greenery adds a natural touch to the tranquil setting, under a colorful sky at dusk.

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

A cozy cabin is nestled among tall trees, featuring a welcoming front porch and a green door. The surrounding lawn is well-kept, with open fields visible in the distance, creating a peaceful and serene setting.

Guesthouse in Jerseyville

4.97 out of 5 average rating, 141 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 modern kitchen features light-colored cabinets and granite countertops. A black stove and microwave complement the space. A small dining table with metal stools is positioned nearby. Natural light filters through a window adorned with plants, adding freshness to the area.

Guest suite in Chicago

4.89 out of 5 average rating, 112 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 bright hallway features large windows allowing natural light to fill the space. Decorative elements include a vintage gramophone positioned next to a wooden side table, framed artwork on the walls, and a few chairs placed along the corridor, adding character to the area.

Apartment in Lake Zurich

4.94 out of 5 average rating, 145 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 rustic cottage is nestled among tall trees, showcasing a natural setting during autumn. Colorful fall foliage blends with the greenery, while fallen leaves cover the ground. The warm tones of the cottage complement the serene landscape.

Place to stay in Cobden

4.94 out of 5 average rating, 313 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.

The historic brick building, featuring a green roof, is surrounded by open grassy areas. Several flags are displayed in front, symbolizing heritage. Multiple sets of stairs lead to various entrances, highlighting the structure's two-story design and outdoor spaces for guests to enjoy.

Home in Pittsfield

4.85 out of 5 average rating, 240 reviews

Florence Guest House

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 OWN K-CUPS!!!***

Top guest favorite

A brick bungalow features a welcoming front porch adorned with a US flag. The porch includes a railing and seating area, while flower pots add greenery. Stairs lead up to the front door, which is detailed with a decorative screen.

Guest suite in Chicago

4.95 out of 5 average rating, 167 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

A single-story residence features a light exterior with a symmetrical layout. A covered entryway leads to large windows that allow natural light. A driveway extends toward a spacious two-car garage, surrounded by well-maintained grass and landscaped plants.

Home in Carthage

4.93 out of 5 average rating, 140 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.

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, 702 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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Convenient locations with everyday essentials

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

4.87 out of 5 average rating, 23 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, 134 reviews

Studio Apartment in Nature Sancturary

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

4.72 out of 5 average rating, 76 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

4.96 out of 5 average rating, 112 reviews

420 at Cheltenham 4BR

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

4.89 out of 5 average rating, 9 reviews

Charming 2 bedroom Apartment

Apartment in Chicago

4.77 out of 5 average rating, 144 reviews

Stylish 1BR South Loop Near McCormick & Wintrust

A living area features a comfortable sofa adorned with patterned cushions. A glass coffee table sits in the center, accompanied by a decorative vase. Natural light filters through the double-hung windows with wooden blinds, complementing the warm wooden floors.

Apartment in Bellwood

4.89 out of 5 average rating, 27 reviews

Bellwood Getaway

A comfortable living area features a blue sectional sofa opposite a modern green chair. A wooden coffee table is centered on a patterned area rug, while two vibrant wall art pieces bring color to the space. Light enters through a tall window, enhancing the atmosphere.

Apartment in Chicago

New place to stay

Stylish 420-3BR Getaway Near McCormick&Grant Park

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, 18 reviews

Spacious Designer Oasis: Game Room - Yard - Garage

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

4.9 out of 5 average rating, 58 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, 39 reviews

Blackberry Hill—Welcome Hunters, Hikers, Bikers

A private dock extends into the calm waters of the lake, surrounded by lush greenery and autumn foliage. The tranquil scene offers a peaceful view, with gentle reflections on the water. Nearby homes can be seen in the distance, enhancing the secluded atmosphere.

Home in Antioch

4.67 out of 5 average rating, 3 reviews

Monthly Rental Petite Lake 4/4 Lakehouse Retreat

A historic home is showcased with a faded blue exterior and a prominent black star on the front. The entrance is framed by a white pergola, and a decorative gate leads to a garden adorned with red, white, and blue bunting, capturing an inviting atmosphere.

Home in Waukegan

4.91 out of 5 average rating, 11 reviews

Historical Hideaway Near Naval Base

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

4.88 out of 5 average rating, 16 reviews

Rejuvenate: 4BR, fenced yard

A modern kitchen is characterized by white cabinetry and elegant granite countertops. Stainless steel appliances, including a refrigerator and stove, are featured. An island provides additional workspace, while a small plant adds a touch of greenery against the dark blue wall.

4.83 out of 5 average rating, 6 reviews

Breeze country home

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.

4.88 out of 5 average rating, 16 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, 310 reviews

Private BR in Condo close to Chicago Dwtwn!

A serene bedroom is illuminated by soft purple lighting. A spacious bed with a polka dot blanket is centered in the room. Floor-to-ceiling glass doors reveal a view of a vibrant city skyline at night, with city lights twinkling in the background.

Condo in Chicago

4.24 out of 5 average rating, 17 reviews

voco: Balcony & City View

A spacious living area features a large sectional sofa draped with a cozy throw. Soft lighting is provided by recessed ceiling lights. A stylish desk and chair are positioned nearby, complementing a picturesque wall-mounted television that serves as a focal point in the room.

Condo in Chicago

4.44 out of 5 average rating, 16 reviews

Urban Oasis: South Shore Chicago

Top guest favorite

A well-lit hallway is adorned with framed artwork and a stylish console table. At the end of the hallway, a cozy seating area with a round dining table and four chairs is visible, illuminated by natural light from large windows.

Condo in Chicago

5 out of 5 average rating, 59 reviews

Where you want to BE! Stylish, Comfy, Luxe

Private room in Chicago

4.86 out of 5 average rating, 84 reviews

Beautiful condo close to the beach

A spacious living area features a large sectional sofa arranged around a coffee table. A dining table is positioned nearby, complemented by four chairs. Natural light enters through multiple windows, illuminating the hardwood floors. A ceiling fan and decorative artwork enhance the casual setting.

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, 274 reviews

Private BR in Chicago - Dwntwn & Fulton Mkt close

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