House holiday rentals in Darien

4.87 out of 5 average rating, 127 reviews

Home in Lake View

Soak Up Mid-Century Style in Wrigleyville and Boystown

This is an architecturally significant (3-bedroom 3.5-bathroom) home by noted Las Vegas architect Homer Rissman. We are located in the heart of East Lakeview, just half a block from Lake Michigan and Lincoln Park, and blocks away from Wrigley Field and Boystown. Smart TVs (with Netflix, Hulu, Amazon Prime) are located in the shared main level TV lounge, and also the lower level lounge. Entire home I like in-person check-in but full privacy is offered You will receive a link with detailed instructions within 24 hours of your check-in. If you have a U.S. mobile number, you will also receive a text message FULL DISCLOSURE: If you haven't used a lockbox (or don't know how to), self-check-in isn't for you. Your check-in should be in person. Lakeview is home to two of the most vibrant sports, nightlife, and theater scenes in Chicago: Wrigleyville and Boystown. Explore souvenir shops and casual eateries by day, and hop from bar to bar along Clark, Addison, and Sheffield Avenues by night. You walk to Treasure Island (half block), Jewel Osco (2 minutes), Whole Foods (4 minutes), Lakeview Athletic Club (4 minutes), XSports Fitness (5 minutes), Walgreens (3 blocks), bars and restaurants aound the corner. Close to multiple buses on Lake Shore Drive. Grab a bus to downtown in 15 minutes You will have to climb one flight of stairs for all bedrooms Street parking is free on the east side of Broadway. The west side requires 383 permits. Please, read the signs.

4.92 out of 5 average rating, 250 reviews

Home in South Elgin

Riverfront rental with fun activity

Riverfront Rental Sits on a quiet street in downtown South Elgin. This home gives you complete access to the Fox River. The bedrooms are on the main level, along with a beautiful kitchen featuring cherry cabinets and an island with breakfast bar, and an awesome four-season porch overlooking the backyard and the beautiful river setting. The second-level loft has great natural light . Outside, you'll find concrete patio and walkway, and stairs leading down to the river and firepit. no pets

4.42 out of 5 average rating, 24 reviews

Home in Carol Stream

Amazing Summer Pool Awaits You!

Vacation, Staycation or Business, you will love your stay at this beautiful paradise with heated pool and tri-level entertainment deck equipped with grill and outside seating and gazebo! Semi-secluded backyard, walking distance to bike path, playground, skate park, walking trails, restaurants and even the gym! Relax on the magnificent deck while watching the sunset This home is pet free and smoke free. Pool is available May-Sept. WiFi is available throughout and Smart TV in the family room.

5 out of 5 average rating, 12 reviews

Home in Cedar Lake

Charming Lake House with Private Lakeside Park

3BR/2BA lake house with private access to lakefront park with an amazing pier, picnic tables, benches on the lake, children's swings, sand, volleyball + more. This gated lake park is the best around! Feel the escape in our charming lake house adorned with lake-life decor. Relax on the woodsy front patio or back porch with lake view. Bonuses: We're on the same block as Bugaboo bar + grill and Bugaboo lake sport rentals. Just a 5-min drive to the iconic Lighthouse restaurant and town grounds.

4.97 out of 5 average rating, 246 reviews

Home in South Elgin

Small Red River House W/Firepit & Tire Swing!

Greetings Airbnb fans! Happy Spring! Here is our family's wonderful riverfront cottage, ready and waiting. A two bedroom 750 sqft house with 1 bathroom on just under an acre property. A special place to relax, do some fishing, grilling, and roasting marshmallows on the fire. Located in a secluded unincorporated Fox River neighborhood in Kane County just a half mile from Blackhawk waterfall via bike path. The subdivision is hidden between the Jon J. Duerr and Blackhawk forest preserves.

4.91 out of 5 average rating, 123 reviews

Home in Homewood

Peaceful & Private Hot Tub Vacation Home Getaway

A Rare gem 💎in the heart of Homewood. This Quaint 2-bedroom remodeled home is charming, sophisticated and discrete. It is minutes away from the Metra station, golf course and downtown Homewood shops. The energy is very calm and quiet ☯️. This is the home away from home where details are everything and the pictures do not capture the essence of this luxurious space. Experience the love, the joy and the peace that continues to leave its mark. Peace and Love - Michael and KP💞

4.85 out of 5 average rating, 167 reviews

Home in Lincoln Park

Historic Old Town, Fabulous 4 Bedroom Home

Lovely Historic 4 Bedroom, 3 bathroom home in Old Town, walking distance of restaurants, boutiques, coffee shops, the lake front and excellent public transportation. 2nd Fl. Master Bedroom has a King size bed and Twin plus private bath with bathtub, walk in shower, w/d; 2nd Fl. two room "suite" with a Queen size bed in each room and private bathroom. 1st Fl. bedroom with Queen bed and private bathroom. Off Street Parking and Private Deck! License Pending.

4.96 out of 5 average rating, 82 reviews

Home in Addison

Home in Unincorporated Addison. RV & Pet Friendly

Your family will be close to everything when you stay at this centrally-located place. This house is extremely family friendly. It has 4 bedrooms and three baths. It has been recently remodeled inside and out. The yard is close to 3/4 acres and has a kids playground and firepit. The driveway is long and can park a long RV if needed. This is a quiet location. Fully Fenced in Yard with lights all around the house. Very safe location.

4.94 out of 5 average rating, 218 reviews

Home in Manteno

Manteno Luxury Comfy Cozy home with- 2 king beds!

Nestled in a cul-de-sac, this open concept 2 bedroom duplex is as cute as a button! There is a fireplace, dining room and convenient patio with sliding glass doors. There are 2 bathrooms. The home is newly remodeled with wood floors and new stainless steel appliances in the kitchen. Each bedroom has a large smart TV for your enjoyment! The living room has a 65 in smart TV and there is also an under the counter TV in the kitchen.

4.84 out of 5 average rating, 248 reviews

Home in Cedar Lake

Vacation home on south end of Cedar Lake

Private two story fully furnished older vacation home on the south side of cedar lake. Both bedrooms and half bath are upstairs. Main level has living room/dining room combo, kitchen and full bath. Short drive to marinas with kayak/boat rentals, public beach and boat launches. Within walking distance is a bar/restaurant with kayak rental.

4.93 out of 5 average rating, 153 reviews

Home in Lake View

Superhost Wrigley/Lakeview Duplex 3BR/2.5BA

Sophisticated Roscoe & Halsted duplex w garden. Sleeps 6 - 3 beds in 3 bedrooms + 2.5 baths. Steps from bars & restaurants, 2 blocks from Wrigley Field & Lake Michigan. Perfect for sports enthusiasts, enjoy Boystown, get-aways. In addition to central heat and air conditioning, ceiling fans with remote control in each bedroom.