Vacation rentals in Crestwood

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Top-rated vacation rentals in Crestwood

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Guest favorite

An updated bathroom features modern fixtures and a walk-in shower enclosed in glass. A vanity with a lighted mirror is accompanied by neatly arranged towels. Decorative floor tiles add a touch of style, while natural light filters through a frosted window.

Apartment in Worth

4.75 out of 5 average rating, 12 reviews

Charming 1-Bedroom in Worth, IL

Welcome to your cozy retreat in Worth, IL! This newly remodeled one-bedroom apartment is perfect for a comfortable and convenient stay. Inside, you’ll find a spacious bedroom with a queen bed, fully equipped kitchen with brand-new stainless-steel appliances, an updated bathroom with modern fixtures, and two Smart TVs and highspeed Wi-Fi. Conveniently situated in the South Suburbs of Chicago near shops, parks, and dining, you’ll also have easy access to major highways and public transportation.

Guest favorite

A renovated coach house is presented with a light yellow exterior, featuring a welcoming entrance flanked by two windows. Lush greenery frames the yard, while a vibrant flower bed and a basketball hoop enhance the outdoor space. A paved pathway leads to the entrance.

Home in Chicago

4.86 out of 5 average rating, 139 reviews

Boho Chic Coach House 30Min to downtown W/ Parking

Whether your looking to stay near family or be close to Downtown. This place has it ALL! This coach house is located in Mt greenwood which is one of the safest neighborhoods in the City of Chicago. It is home to many police, firefighters and teachers. Downtown is a quick 30 minute drive and there are also many bars and restaurants in walking distance. The home has been totally renovated and stocked with all the essentials. All you need to do now is pack your bags and enjoy your vacation.

Guest favorite

A charming train station exhibits a classic architectural design, featuring a red-tiled roof over an arched entrance. Stone walls and large windows create an inviting facade. Benches are positioned along the platform, while train tracks extend in the foreground under a softly lit sky.

Home in Oak Forest

4.97 out of 5 average rating, 33 reviews

The Oasis, 3BR/2BA Zen Hideaway

Welcome to The Oasis, a blend of modern elegance and boho charm in a serene neighborhood. This 3BR, 2BA retreat offers an open-concept living space with white walls, black railings, and light wood floors. Enjoy cozy living, a modern chic look throughout the house, kitchen with stainless steel appliances and equipment. Modern bathrooms provide a relaxing experience. Conveniently near attractions and dining, The Oasis is your perfect escape. Book now to enjoy comfort and style.

Top guest favorite

A sleek keypad entry system is mounted on the doorframe, featuring numerals and a circular keyhole. The brushed metal finish adds a modern touch, while the textured gray wall provides a subtle backdrop.

Guest suite in Orland Park

4.98 out of 5 average rating, 98 reviews

Private Guest Suite 2 Cozy Rooms

Private guest suite with separate entrance. Sitting room, kitchenette, bedroom w/queen bed, private bath, plus twin sofa bed in sitting room. Great alternative to hotel for business trip or visiting the area. Conveniently located in southwest suburbs of Chicago, 40 minutes from downtown by car (non rush hour) or Metra lines a few miles from the house. Set near a golf course and forest preserve, nearby to multiple restaurant and shopping districts less than 10 minutes away.

Guest favorite

A street view in a quiet neighborhood depicts a wide avenue lined with storefronts, including cafes and shops. A sidewalk runs alongside the road, offering a clear path for pedestrians. Trees cast shadows on the pavement under a bright, blue sky with scattered clouds.

Home in Blue Island

4.82 out of 5 average rating, 200 reviews

Warm and comfortable inviting Suburban home !

160 year old land mark community, Framed cedar bevel siding 2 story home, front porch , 10 ft high ceilings, kitchen canned lighting home. 6 feet fence In closed yard, whole house water filtration system , Quite neighborhood with sidewalks . 19 miles to downtown Chicago , Metra train station and bus route, in walking distance . driving to the city of Chicago 5 minutes to major expressways . Host is willing to be available for any and all information 24/7.

Top guest favorite

Yurt in Homewood

4.97 out of 5 average rating, 109 reviews

Glamping Yurt&RV-Game Room-Pool-Sauna-Hotub Court

Glamping Experience to the NEXT LEVEL! Opened April - Nov. Contact during off season. Mini Resort Includes: RV w/bathroom - 2 beds & sofa sleeper 20' Safari Yurt - 4 beds w/sofa sleeper Game Room w/bathroom 1 bed & sofa sleeper Gazebo w/2 twin beds Outdoor wooden Barrel-Sauna 27' above ground Pool 6-7 Person outdoor hot-tub Fresh Eggs seasonally Mini Golf lanes Basketball, Volleyball, Pickleball court Breakfast included is 1 dozen fresh eggs!

Guest favorite

An inviting entrance features a dark door flanked by large windows, framed by a small patio. Snow lightly dusts the surrounding plants and seating, which includes two chairs and a table. Potted flowers add a touch of color to the winter scene.

Tiny home in Burr Ridge

4.9 out of 5 average rating, 377 reviews

Less is more! Pet friendly Tiny Home near Chicago!

Less is more--see for yourself how big 250 square feet can really feel! For those who would love to try tiny living and a minimalist lifestyle, this is the perfect getaway. This tiny house has everything you will need to fall in love with tiny living! There is a fenced yard, grass area for furry friends, free parking and is close to hiking trails, restaurants, shops, breweries, bars, and Chicago! Check us out on Insta: @LessIsMore_TinyHome

Top guest favorite

A stylish hanging chair is mounted on a sleek, white metal stand. The chair features a woven rattan design with a soft, light-colored cushion. Natural light enters through the adjacent window, highlighting the chair's unique structure against a soft, pastel wall.

Apartment in Blue Island

4.94 out of 5 average rating, 298 reviews

Charming Unique 2 Bdrm Apartment in Victorian Home

My place is close to the excitement and culture of the beautiful city of Chicago. It is a short walk to Metra trains with a 25 minute ride downtown. You’ll love my place because of the diverse, comfortable, quiet, tree lined neighborhood where you can relax and feel secure. It is close to expressways, golf courses and a local park with walking path. The apartment is not available to guests without previous positive reviews.

Guest favorite

An outdoor patio is illuminated by soft lighting under a protective shelter. Comfortable seating arrangements include folding chairs and metal benches. In the center, a fire pit is surrounded by stones, with flames providing warmth and a calming ambiance during the evening.

Home in Chicago Ridge

4.92 out of 5 average rating, 139 reviews

Quiet cul-de-sac with huge fenced in backyard

3 bedroom, 2 bath ranch home on a quiet cul-de-sac. Big fenced in backyard for the kids, dog, & adults to play during the day, then relax by the fire at night. Walking distance (50 ft.) to the bar/restaurant with private entrance. 15 miles (25 mins) from downtown Chicago. And for you couples, come back home from your busy day, sit back and relax in the 8 jet jacuzzi whirlpool tub that will comfortably fit both of you.

Top guest favorite

The kitchen area features modern appliances, including a stainless-steel refrigerator and oven. A kitchen island offers additional prep space, while a dining table set for four provides a welcoming spot for meals. Light-colored cabinets complement the dark tile flooring, creating a functional cooking space.

Apartment in Hickory Hills

4.96 out of 5 average rating, 45 reviews

Cozy Guest Suite. Private Entry+ Turo Rental

3600 sqf single family home with a Guest Apartment and private entry on the ground level. Your family will be close to everything when you stay at this centrally-located place. Centrally located off of I294, I55, I57 and I80. Easy to and from travel. In Need of a rental we have 2018 Jeep Grand Cherokee High Altitude at the house and listed Turo.

Superhost

The living room features two blue armchairs positioned next to a wooden coffee table with decorative items. A mounted flat-screen television is visible above a modern shelf, while an area rug in vibrant colors complements the wooden floor.

Apartment in Morgan Park

4.83 out of 5 average rating, 89 reviews

2 bedroom lovely spacious Suite

This stylish place to stay is perfect for any event. 420 friendly. Come and let us pamper you. Come and enjoy are tree lined community in the historical Beverly community. This Suite has all the latest amenities and beautifully furnished. Make some memories at this unique and family-friendly place.

Guest favorite

A boxed game titled 'Jumbling Tower' features a stack of wooden blocks in various configurations. The packaging displays a vibrant blue background with a visually engaging design, while the blocks are shown in a natural wood finish, suggesting a classic game suitable for multiple players.

Home in Oak Forest

4.92 out of 5 average rating, 102 reviews

Cheerful three bedroom, 2 full bath in Oak Forest

Beautifully updated 3 bdrm 2 ba home in Oak Forest! Upgraded kitchen cabinets with stainless steel appliances with a large eat-in kitchen. 2 full baths, plenty of room for entertaining in family rooms. A vending machine conveniently located downstairs. Majestic private backyard.

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Other great vacation rentals in Crestwood

A countertop features a Keurig coffee maker in a sleek design, positioned next to a container holding various kitchen utensils. A small bowl made of stone sits nearby, showcasing a neutral color palette against the light marble surface.

Apartment in Frankfort

5 out of 5 average rating, 3 reviews

Studio 2B at The Kreger House

JorgeRating, 5 stars1 week ago

Really enjoyed my stay here. The place was clean, comfortable, and in a great location—super convenient for getting around. The host was great—very clear with instructions, super responsive, and genuinely helpful throughout the whole stay. Would definitely book again.

A modern kitchen features wooden cabinetry and a central island with a stovetop and stainless steel range hood. Dark dining chairs surround a table in the adjacent dining area, which is illuminated by a contemporary light fixture. Gray and white backsplash tiles add texture to the space.

Home in Markham

4.87 out of 5 average rating, 31 reviews

“La Cabaña” Entire 2 bd near Chicago

EricRating, 5 stars1 month ago

Nice place in a good location that fit our needs

An outdoor seating area is set up with six cushioned chairs arranged around a central glass table. A patterned area rug adds color, while a fire pit is positioned nearby, creating a cozy ambiance for gatherings.

Home in Calumet Park

4.76 out of 5 average rating, 90 reviews

My quaint little escape

FredrickaRating, 5 stars1 day ago

Thank you Ms.Tracy for allowing me & family to stay at your beautiful home. I love & enjoying the home very cozy & relaxing & beautiful.

Guest favorite

A modern kitchen features a large central island with a marble countertop and bar seating. Stainless steel appliances, including a refrigerator and oven, are positioned alongside ample gray cabinetry. A pendant light fixture hangs above the island, and natural light enters through a skylight.

Home in Orland Hills

4.95 out of 5 average rating, 20 reviews

Orland hill’s rental

VictoriaRating, 5 stars3 weeks ago

We really enjoyed our stay here! There was plenty of space for 6 adults and a child with many places to hang out. The neighborhood was nice and the house was very clean. It was great to spend time in the backyard with the nice weather we had.

Guest favorite

A black car is parked on a gravel driveway beside a blue house. The scene includes a set of stairs leading to the house's entrance, with large windows visible. Lush trees and landscaping surround the property, suggesting a suburban environment.

Private room in Richton Park

4.85 out of 5 average rating, 241 reviews

Urbal retreat

RobertRating, 5 stars1 week ago

The host was great, we loved the cozy room and amenities. The shower was very clean and nice. Great spot for if you’re just passing through.

Guest favorite

A bowl of salad features succulent grilled shrimp atop a bed of greens. Slices of avocado and crispy tortilla strips add texture. The dish is presented in a white bowl with a blue rim, placed on a rustic wooden table beside a blue and white striped cloth and fork.

Hotel room in Rosemont

4.92 out of 5 average rating, 273 reviews

Relaxing Standard Room l Free Airport Shuttle

AlexeiRating, 5 stars2 weeks ago

easy check-in, super clean, friendly staff. parking is easy and affordable. will definitely be staying again!

Guest favorite

A bright living area features large bay windows adorned with sheer drapes, allowing natural light to fill the space. A glass coffee table is centered on an area rug, complemented by a sofa and elegant dining set that comfortably seats six. Decorative accents enhance the surroundings.

Private room in Blue Island

4.9 out of 5 average rating, 231 reviews

Chicago commuter room

MargaretRating, 5 stars5 days ago

I throughly enjoyed my stay at Karen’s house. She knew Chicago very well and was helpful in guiding us to where we needed to go. Her home was very comfortable and we really felt at home.

Guest favorite

A modern interior space features a striking geometric black accent wall, complemented by a green wall. A large mirror reflects the room, and a small potted plant adds a touch of greenery. A wooden sliding door leads to another area, with a workspace visible beyond.

Home in Homewood

5 out of 5 average rating, 10 reviews

Charming 2BR with Fireplace

StaceyRating, 5 starstoday

This house has everything you want or need. It was warm and inviting. We enjoyed it so much we didn't want to leave. We loved the yard and the art in the house. Even the neighbors were friendly. Only Jesus is perfect. This house is excellent. Thank you so much for everything.

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Vacation rentals in Crestwood

Top-rated vacation rentals in Crestwood

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