Holiday rentals in Barrington Hills

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Top-rated holiday rentals in Barrington Hills

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite

A spacious living area features a large, light grey sectional sofa positioned around a circular coffee table. A vibrant area rug adds color beneath the furniture. A wall-mounted TV is visible above a white fireplace, with natural light filtering through sheer curtains.

Townhouse in Hoffman Estates

4.96 out of 5 average rating, 78 reviews

Game Room | Exercise Area | Firepit | Sanitized

Make yourself at home in this cozy, private townhouse, perfect for families and groups! Conveniently located 20 min from O’Hare, 40 min to downtown Chicago, and near NOW Arena, Schaumburg Convention Center, Woodfield Mall and St. Alexius Hospital. Sanitized after each guest, it features a full kitchen, family games, foosball table, walking pad, Smart TVs, fireplace, laundry room, and a yard with a firepit. With extra futons in the basement, there’s plenty of space. Message me with any questions!

Guest favourite

A spacious bed with plush pillows is positioned against a backdrop of exposed brick walls. Natural light filters in through a large window, adorned with elegant curtains. A bedside table with a lamp complements the cozy ambiance.

Loft in West Dundee

4.96 out of 5 average rating, 393 reviews

Hip Urban Loft-Small Town Charm - 124 LOFTS #1

Luxury one-bedroom loft in the heart of downtown Dundee. Newly renovated 125-year-old building with timber ceilings, exposed brick walls and beautifully restored hardwood floors. Tastefully decorated and features a king-size Beautyrest mattress, luxury bed linen, private bathroom, kitchenette with under counter refrigerator, Kuerig coffee maker and lightning fast Wi-Fi for streaming your favorite shows on the 60” LED smart TV. 124 LOFTS offers 4 separate luxury lofts. Book one Loft or all four.

Guest favourite

A bright living area features a comfortable sofa arranged around a modern coffee table. A work desk is positioned near the window, with natural light spilling in. Artwork adorns the walls, and greenery adds a touch of life to the space, enhancing the welcoming atmosphere.

Flat in West Dundee

4.93 out of 5 average rating, 127 reviews

Charming Riverfront Stay | Heart of Downtown

Welcome to The Riverfronts! Three boutique hotel rooms perfectly situated along the river in downtown West Dundee, offering scenic views and modern comforts. ✔ Riverfront Location: Enjoy the scenic riverwalk just steps away. ✔ Prime Downtown Spot: In the heart of downtown Dundee, minutes from top attractions and dining. ✔ Exclusive Group Booking: Reserve just one or all three units for your entire party. ✔ Outdoor Firepit: Unwind by the firepit, perfect for evening gatherings. ✔ Sleeps 4: Each

Guest favourite

An outdoor patio area features a round table with four accompanying chairs. A large blue umbrella provides shade over the seating. Lush greenery and colorful flower beds surround the space, while a charcoal grill is positioned nearby for outdoor cooking.

Flat in Algonquin

4.9 out of 5 average rating, 31 reviews

Waterfront 2 Room Studio w/Kitchenette, Downtown

Casual Living - Prairie Trail Apartment Studio apartment overlooking the Fox River. Walking distance to downtown Algonquin with kitchenette and bathroom. Free business class wifi & cable TV. Don't impose on family or friends, or settle for the bland experience of a box hotel. Instead, book a comfortable stay with great amenities and enjoy the river and downtown entertainment. Relax, get a restful sleep, and enjoy your visit. Little touches & the extra effort assure you have an awesome stay.

Top guest favourite

A well-defined stone pathway leads to the entrance of the prairie-style home, bordered by lush green grass and neatly trimmed hedges. Hanging flower baskets add vibrant touches above the cozy seating area, surrounded by the serene backdrop of towering oak trees.

Guest suite in Riverwoods

4.95 out of 5 average rating, 445 reviews

Master qtr close to nature & easy urban facilities

This amazing prairie style home sits on 2 acre land surrounded by lush lawn and majestic oak trees - a nature lover's dream with unparalleled serenity. Vacation-like setting blends country-like quiet with nearby conveniences including shopping, trains, restaurants, highways, Ravinia (18 MINs drive). 5 MINs to I 294. 20 MINS to O'HARE; 5 Mins to Discover, Baxter; 10 MINs to Walgreens Deerfield campus, TRINITY INT'L UNIVERSITY; 15 MINS to Lake Forest Academy. 25 MINs to Great Lakes Navy Base.

An aerial view captures the serene Fox River, flanked by neatly arranged homes and lush greenery. Sidewalks line the waterfront, while docks extend into the water. The image conveys the peaceful ambiance of the area, highlighting the connection between nature and residential living.

Home in Algonquin

4.83 out of 5 average rating, 48 reviews

*COZY HOME near downtown and fox river*

Our home is in a safe and quiet lot near downtown Algonquin and close to the park, bike trails, shops, and dining. Views of the Fox river and close to Marina. Updated home with an open concept, modern decor and finishes. Full kitchen with MW, toaster, k-cup, and W/D.2BD with queen sz beds, memory foam mattress and flat screen TVs, 2 full BR. Linens and towels included.Small loft with sofa bed. LR also offers a queen size sofa bed, ROKU smart TV and 5G Wi-Fi. Weber grill is outside.

Top guest favourite

A serene living area features a large sliding glass door leading to a deck with unobstructed views of Round Lake. Natural wood accents adorn the wall, while a plush sofa and a small coffee table create a relaxing seating space.

Home in Round Lake Beach

4.99 out of 5 average rating, 179 reviews

Round Lake Getaway Retreat

Looking for a calming, peaceful lakeside getaway for you and your loved one? Come stay at our remodeled retreat with private waterfront access to Round Lake. Enjoy peace and reflection meditating on the spirited lake waters rolling into shore. Wake up to inspirational lake views with soul warming coffee, tea or cocoa. Savor deep or lazy conversation with your loved one, surrounded by dreamy décor and captivating nature. Come and relax, restore, and rejuvenate by the lake!

Guest favourite

The exterior of a charming historic home features dark blue siding and a welcoming front porch with three steps leading up to the entrance. Large windows on either side of the door allow for natural light, while lush greenery surrounds the property, enhancing its curb appeal.

Home in Elgin

4.89 out of 5 average rating, 135 reviews

Charming Elgin Home with a Great Location

Come enjoy this beautifully restored and charming historic home from the early 1920s. Our place is good for couples, families or for a getaway with friends. Outdoor space with fully fenced backyard. This 2 bed 1 bath has been fully restored and is absolutely adorable! Walking distance to downtown Elgin (less than one mile) and Metra station (only one hour train ride into the city!), and less than 5 minute drive to I-90. Relax and get cozy in this adorable space.

Guest favourite

A cozy living area features a black leather sofa paired with decorative pillows. A glass coffee table sits atop a patterned rug, complemented by a lamp and a small plant. The staircase leads to an upper level, with a wall map artwork enhancing the space.

Townhouse in Hoffman Estates

4.9 out of 5 average rating, 362 reviews

a SIMPLE place

Booking the entire house with 100% privacy. It has 2 driveway parking spaces and street parking. Garage may be available. CHECK-IN and OUT are flexible. I set checkout at 11am (text me if you need late checkout). The space is perfect for a family of 4. It is located about 20 minutes from O'Hare airport and 40 minutes from Chicago downtown. Infants and pets are welcome (please text me for over size pets or more than 2 pets) Play pan is available upon request.

Top guest favourite

A charming cottage is framed by lush greenery and colorful flower planters. The white exterior features multiple windows, allowing ample natural light. A welcoming front porch leads to the entrance, adorned with patriotic bunting, inviting guests to enjoy the serene surroundings.

Cottage in Barrington

5 out of 5 average rating, 122 reviews

Cozy French Inspired Cottage in rural setting

Relax and escape to our charming, one of a kind cottage. Beautifully decorated with period furniture and tastefully updated with modern amenities. The cottage offers slate tile and hardwood floors. Original pine floors line the upstairs loft bedrooms. Cook in a French inspired country kitchen with butcher block counter tops. Rural setting, yet minutes away from everything! Downtown is a 20 min. walk and the Metra will take you to the city in 45 minutes!

Guest favourite

The exterior of the Victorian Sherwood House showcases its distinct pink siding accented with green trim. Stained glass windows add character, and multiple gabled roofs enhance its architectural design. A canopy of trees provides a natural backdrop to this charming residence.

Flat in Elgin

4.81 out of 5 average rating, 187 reviews

Sherwood House

Enjoy the ambience of the Sherwood House, an 1884 Victorian built for Judge David Sherwood. Use of entire first floor apartment including a full kitchen is perfect for longer term stays. Original features include multiple stained glass windows, beautiful wood work, multiple decorative fireplaces and hardwood floors. Located just blocks from downtown Elgin, walk to shops, restaurants, the casino, bike trail or Metra. WiFi and off street parking.

Superhost

The kitchen features white cabinetry and stainless steel appliances, complemented by a tiled backsplash. A dining table with eight wooden chairs is positioned under natural light from large windows, creating an inviting space for meals.

Home in Carpentersville

4.87 out of 5 average rating, 134 reviews

4BR Home w/ Game Room • Ideal for Longer Visits

Looking for a cozy getaway or a comfortable home-away-from-home for a mid-term or extended stay? Welcome to our updated 4-bedroom, 2-bath ranch in Carpentersville—designed for families, work travelers, relocation stays, and anyone needing longer accommodation. Enjoy nearby attractions like Santa’s Village, Paintball Explosion, NOW Arena, and Spring Hill Mall—all within 10 miles or less. Book instantly and secure your stay today!