Vacation rentals in Berwyn

4.96 out of 5 average rating, 340 reviews

A lush garden pathway winds through vibrant flower beds and greenery, leading to a cozy seating area nestled under a tree. The stone path is framed by various plants, showcasing a tranquil outdoor setting perfect for relaxation.

Guest suite in West Town

Secret Garden @ The Noble Farmhouse | Wicker Park

While our place truly is a tucked away secret sanctuary, we are also in a sweet spot of ULTRA CONVENIENCE. Wicker Park/Noble Square/West Town has many great bars & restaurants & is an amazing location for exploring the city. WALK to the action on Division St. or Chicago Ave, Chicago's upcoming gallery district. A 1/2 block to the 56 bus takes you to the Loop in 10 min, or to the heart of Wicker Park in 5. A 10 min walk to the BLUE LINE serving O'Hare & Downtown. And Divvy bikes 1/2 block away.

5 out of 5 average rating, 13 reviews

The exterior of a historic brownstone building is showcased, featuring a beautifully detailed entrance surrounded by brick and stone. A set of steps leads up to the front door, flanked by decorative wrought iron railings and lush greenery, creating a welcoming atmosphere.

Home in Lincoln Park

Top Floor in Historic Old Town!

Unbeatable Location in Historic Old Town Triangle! This charming top-floor apartment is on a quiet cul-de-sac in the heart of Old Town Triangle, steps from St. Michael’s Church, North Ave Beach, Lincoln Park Zoo, and Wells Street’s entertainment district. The sun-filled space features an oversized private patio, and 3 bedrooms with queen beds, closets, and dressers. The spacious kitchen and dining areas are perfect for gatherings. The “L” stop is just two blocks away for easy access to the city.

Apartment in West Lake View

A spacious living room features large windows allowing natural light to fill the space. A comfortable light-colored sectional sofa is situated in front of a glass coffee table, with a medium-sized rug underneath. A wooden side table and a television mounted on the wall are also visible.

4.94 out of 5 average rating, 179 reviews

Sun drenched 2 bedroom 1 bath with Kitchen & W/D

Welcome to beautiful Roscoe Village! Come relax and enjoy a gorgeous loft-like condo that has a huge sun-drenched living room and opens up right to the kitchen. Enjoy cooking on your own in the spacious kitchen and rest easily at night in a spacious king bed in the main bedroom. We love and welcome pets - so no need to leave your fur baby at home. Uber to Wicker Park and Logan Square. You’ll have your own private entrance with a lock box to get into the condo. We look forward to hosting you!

5 out of 5 average rating, 20 reviews

A modern kitchen area is characterized by sleek white cabinetry and stainless steel appliances. A white countertop hosts a small sink and stylish seating for two at the breakfast bar. A plant adds greenery, while natural light pours in through large windows.

Apartment in Bridgeport

CitySlickers/FreeParking/Laundry/FastWiFi!

-600 sq.ft apartment / 1st floor / -Free parking pad in rear / free street parking -Commute to Downtown: 15min (drive) / 28min (transit/train) / 22min(bike) -Walk score 93! Bike Score 92! Near Trains to Downtown!! -Gated access w/ Building video and security alarm system and noise monitoring equipment. -Kitchen is stocked w/ cookware, utensils, etc. -Washer and Dryer and Dishwasher in unit (free) -Rideshare(Uber/Lyft) / Bikeshares(Divvy) are bountiful -Safe, working class neighborhood

5 out of 5 average rating, 13 reviews

A dining area showcases a large wooden table surrounded by eight wooden chairs. A vintage map hangs on the wall, adding character. Natural light enters from nearby windows, illuminating the space. A stylish lamp and greenery are present, complementing the inviting atmosphere.

Home in Avondale

Alluring Avondale Abode

Welcome to Alluring Avondale Abode, the perfect vacation rental for your next family trip or group getaway. A pet-friendly paradise, centrally located for easy travel to all the top attractions. A spacious kitchen, beautiful backyard deck, and patio create a wonderful backdrop for entertaining and relaxing. Find an array of fun games to keep all ages occupied. Book now and experience the laid-back vibe and unbeatable amenities that will make your vacation truly unforgettable.

Apartment in East Rogers Park

A vast sandy beach extends toward the horizon, where gentle waves meet the shoreline. A harbor pier is visible in the distance, leading to a lighthouse. Dune grass and a wooden fence mark the beach's edge, with an overcast sky providing a soft, diffused light.

4.95 out of 5 average rating, 80 reviews

Loyola & Lake -3br/2bth close to the Lake & Loyola

Amazing lake views from 2 outdoor spaces! This lovely 3 bedroom, 2 bath unit has a large front balcony and also a rear deck looking out to the lake. The unit has an updated kitchen & 2 baths, a dining area, in unit laundry & a spacious living room with a fireplace & lots of books and games to keep you entertained! Walking distance to restaurants and bars. Starbucks is a short walk down Sheridan. Kayak/paddle board rental available (May 1-Oct 15th), weather permitting.

4.85 out of 5 average rating, 68 reviews

A cozy living room features four plush purple chairs arranged around a circular table. A modern television is mounted above a white brick fireplace, complemented by bookshelves filled with various items. A large potted plant adds a touch of greenery, enhancing the warm atmosphere.

Home in Austin

A Comfortable Stay While You are Away in Oak Park

Welcome to this Oak Park home, conveniently minutes from the main expressway, train station, downtown Chicago, and the Medical Center. This entire Oak Park house is ideal for travelers seeking a tranquil and welcoming space to unwind in after a long day, medical professionals, visiting patients at the Medical Center, and families needing long-term housing. The residence is minutes from downtown Oak Park and the historical landmarks of Frank Lloyd Wright's home and studio.

Apartment in Logan Square

A bright living space features a sectional couch positioned around a glass coffee table. Large skylights and windows allow natural light to fill the room, which is accented by a decorative rug and a modern electric fireplace. A television hangs on one wall, displaying a scenic landscape.

4.92 out of 5 average rating, 12 reviews

2-level PH w/ 2 Luxe Suites Combined; Spa Access

The top floor sprawling ranch with duplex down offers sky & outdoors views, privacy, & cathedral ceilings, it is connected to your rear 2nd floor suite with 10ft ceilings. A burgeoning neighborhood next to the 606 Trail Amenities: - Uber-fast Wifi streaming, - Hot tub house - 80" + 75" hi-def tv's - 3 sectional couches - European decor - 2 kitchens - The popular 606 Trail access is 100 ft away, - YMCA across the street with indoor Olympic size & kiddie-pools!

4.85 out of 5 average rating, 34 reviews

The exterior of the tiny house is shown, featuring a light grey façade with two symmetrical windows on the upper level and a white door at the bottom. A wooden staircase leads to the entrance, surrounded by minimal landscaping and a clear blue sky above.

Guesthouse in Evanston

Tiny house in West Village Arts District

This tiny house (750 sq ft) invites you to explore Evanston's West Village Arts District and shop creative businesses. Just down the block is the newly renovated Robert Crown Recreation Center, where you can check out library books and movies, play soccer, tennis, ice hockey and go ice skating year round. This Tiny House is located in our backyard, so please be respectful of noise and the amount of guests you book on the reservation!

4.88 out of 5 average rating, 75 reviews

A bright entryway features a wooden floor and white walls, leading to an open living space. A glass-front cabinet showcases various dishware, while a dark wooden door provides access to another room. Natural light fills the area, enhancing the vintage charm.

Apartment in Lake View

Spacious 2 Bed Apartment, Perfect Location

Located just blocks away from the Brown Line CTA stop, This massive 2 bedroom apartment will add some vintage charm to your vacation in a safe, low key neighborhood while never taking you far from the action. This unit is ideal for travelers looking for a comfortable home base while exploring everything downtown and the north side of Chicago have to offer.

4.95 out of 5 average rating, 104 reviews

A modern kitchen features sleek dark cabinetry and stainless steel appliances. Natural light enters through skylights, highlighting a small dining table with two chairs. The warm wood flooring complements the design, while a light fixture hangs gently from the exposed beam ceiling.

Guesthouse in Oak Park

O'Malley Oasis!

Your home away from home at this centrally-located coachhouse apartment.Queen sized bed, fully equipped eat-in kitchen, relaxing living area with recliner, leather couch and big screen tv. Walk to downtown or explore Chicago via public transportation just a few blocks away. Adorable porch and your own entry. Parking spot included!

4.96 out of 5 average rating, 281 reviews

The exterior of a three-story residential building is depicted, featuring a wooden porch with steps leading to the front door. Large windows allow natural light to enter, and greenery surrounds the entrance, complementing the light-colored siding and red brick foundation.

Apartment in Irving Park

Spacious 1BR apartment in a central location

Private 1BR in Avondale neighborhood of Chicago. Right off the Expressway, it's 20 mins from O'Hare, 20 mins from Downtown (both by Blue Line) 20 mins from Wrigley Field (bus). Comfortable and spacious attic apartment in a residential area. Lots of street parking.

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Popular amenities for Berwyn vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Berwyn's top sights

FitzGerald's25 locals recommend

Buzz Cafe8 locals recommend

Oak Park Conservatory18 locals recommend

SEN Sushi Bar14 locals recommend

Bodhi Thai Bistro6 locals recommend

Autre Monde Cafe & Spirits4 locals recommend

Other great vacation rentals in Berwyn

4.93 out of 5 average rating, 42 reviews

Home in West Lawn

Family Friendly Duplex/9 min from MDW/Free Parking

4.86 out of 5 average rating, 42 reviews

A modern kitchen features sleek white cabinetry and stainless steel appliances. A large granite island provides additional workspace and seating. Natural light from the windows brightens the space, while a dining area with wooden chairs is visible in the foreground.

Apartment in Albany Park

Elegant 4Bedroom with Free Parking in Albany Park

Apartment in Jefferson Park

A modern kitchen is equipped with sleek stainless steel appliances, including a microwave and dishwasher. Light countertops complement dark cabinetry, while a small countertop with two barstools provides a casual dining option. Natural light filters in through a window near the door.

4.63 out of 5 average rating, 27 reviews

City Gem: Stylish 3BR for Urban Explorers

4.83 out of 5 average rating, 101 reviews

A modern kitchen is equipped with stainless steel appliances and white cabinetry. Natural light fills the space through two large windows. A white farmhouse sink is complemented by a dark wooden countertop, while a patterned rug lies on the hardwood floor.

Home in Logan Square

California Cottage/4br prime location Logan Square

Condo in East Rogers Park

The exterior of a three-story Art Deco building is showcased, featuring a light-colored brick facade and large, symmetrical windows. A wrought iron fence surrounds the property, with well-maintained greenery enhancing the entrance. The sky above offers a clear blue backdrop.

4.81 out of 5 average rating, 31 reviews

Spacious condo with open floor plan and fireplace

4.79 out of 5 average rating, 185 reviews

A green, two-story house is framed by large trees in a quiet neighborhood. The front features a central door with a decorative window and light-colored trim. Leaves cover the ground, indicating the autumn season. The pathway leading to the entrance is bordered by grass.

Home in Cicero

Spacious whole apt near shopping and city

5 out of 5 average rating, 25 reviews

A modern kitchen area features a white bar counter with four dark wooden stools. Minimalistic tableware is arranged on woven placemats. Large windows allow natural light to fill the space, showcasing a glimpse of the outdoors through the decorative glass door.

Home in Lombard

Spacious Home in Chicago Suburbs