Holiday houses in Kildeer

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Top-rated holiday rentals in Kildeer

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

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Top Guest favourite

The backyard features a well-maintained lawn surrounded by gray gravel. A patio area includes a dining table and umbrella. The house is painted in a soft blue, while a grill is positioned near the side of the house. A condo building is visible in the background.

Home in Wauconda

4.97 out of 5 average rating, 102 reviews

The Adorable "Blue Breeze"!

Enjoy time at our centrally-located, family-friendly home. Close by, you'll find a public fishing dock and the popular Phil's Beach. A peaceful space with an outside patio and grill, perfect for relaxing at end of day. We also have a large driveway that can accommodate your boat making it easy to enjoy a day on Bangs Lake or a short 15 min trip to Fox Lake. Nearby attractions include the Volo Museum, Jurassic Gardens, and Lake County Discovery Museum. Please note the backyard is not fenced in.

LocationFamilyOutdoor spaces

Top Guest favourite

A modern two-story home is showcased from an aerial perspective, featuring a neatly trimmed yard and a fenced area. The property is positioned near a marina, with views of parked boats on the lake. An attached garage is visible, along with a spacious driveway.

Home in Wauconda

4.99 out of 5 average rating, 81 reviews

Modern 4BR Lake Retreat • Walk to Beach & Main St

Lakeside Haven, a 4BR retreat on Bangs Lake. Steps from Main Street’s dining, shopping, and beaches, this modern home offers:  🌊 Lake views & open living spaces 💻 High-speed Wi-Fi & workspace 🍳 Fully equipped kitchen & laundry 🚤 Nearby hiking, boat rentals, & events 🛏️ King & queen beds 🪟 Blackout screens Perfect for families, Navy graduations, and long stays. Enjoy the Triathlon, farmers market, cruise nights, ice fishing derby, and more. Dates fill quickly in every season. Book today!

LocationValueIndoor spaces

Top Guest favourite

A fire pit placed on grass is surrounded by two chairs, creating a cozy gathering space. Flames dance brightly against the night backdrop, and a wooden fence provides privacy. The area is softly illuminated, inviting relaxation in the outdoor setting.

Guest suite in Lake Zurich

4.93 out of 5 average rating, 68 reviews

Private Guest Suite • Sleeps 4 • Separate Entrance

⭐ Private walkout entrance ⭐ 1000 sq ft private guest suite ⭐ Fenced backyard + patio + fire pit ⭐ Pet friendly ⭐ Free driveway parking Welcome to beautiful Lake Zurich! This 1000 sqft walkout awaits you. The fenced yard makes it a pleasure to welcome your furry family members too. Whether you are here for an adventure or business, a couple, family, or a group of friends -please enjoy your stay! ✨ Our space is best suited for guests looking for a comfortable, quiet, and relaxing stay!

LocationFamilyPets

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, 506 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.

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Superhost

A bright and inviting living room features a circular red sectional sofa with various cushions. Large windows allow natural light to fill the space, with views of the outdoor area. A low wooden coffee table rests in the center, complemented by a neutral area rug.

Home in Lake Zurich

4.78 out of 5 average rating, 79 reviews

5BR with Sauna, Game Lounge, Poker Room, Darts etc

Welcome to The Gathering House, a massive 4-level retreat in Lake Zurich created for real together-time. With 5 bedrooms, 3 living rooms, 10-seat dining room, fully equipped kitchen with extras like a Crock-Pot and fondue set, it’s ideal for families, friends, or reunions. After game night in the basement with pool, poker, and darts, sauna, head out to nearby lakefront beaches, parks, trails, groceries, and local dining spots just minutes away. Brand new carpet on the top floor.

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Guest favourite

A charming bungalow exterior presents a warm facade with well-maintained landscaping. Features include a welcoming front staircase with wrought iron railings, potted flowers under large windows, and a flag hanging from the porch. A lush green lawn surrounds the home, enhancing its inviting presence.

Bungalow in Mundelein

4.88 out of 5 average rating, 248 reviews

Quaint Bungalow, near Great Lakes Naval Base

This cozy bungalow is located 41 miles north of Chicago; 60 miles south of Milwaukee, WI; and just 12 miles west of Great Lakes Naval Base. Nearby train stations make Chicago just a 45-minute train ride away. O'Hare Airport is a 30-40 minute commute from our home. Additional nearby sites include Great America, and shopping venues--from outlet malls in Gurnee and Kenosha, to quaint downtowns, like Libertyville. Location makes this home an ideal venue for Midwest sightseeing.

LocationFamilyAmenities

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, 393 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.

ValueFamilyWi-Fi

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

4.99 out of 5 average rating, 142 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!

ValueFamilyAccess

Top Guest favourite

The exterior of a modern ranch-style home is showcased, featuring a strategic arrangement of greenery and colorful landscaping. A paved driveway leads to a welcoming entrance, flanked by two garage doors. The home is complemented by a clear blue sky and mature trees in the background.

Home in Schaumburg

4.93 out of 5 average rating, 101 reviews

Cozy Schaumburg 5 br/3.5ba w/ bonus rooms/office

Luxurious–Cozy Ranch Stunning 5-bedroom, 3.5-bath home offers spacious modern living on a quiet cul-de-sac. The home features a gourmet kitchen with a Viking 48” stove and Omega cabinets, a master suite with a coffee bar, his-and-hers bathrooms, and a jacuzzi tub. Enjoy two fireplaces, three wet bars, and a basement with a pool table, arcade games, an 85” TV, and a kids' playroom. Outside, the backyard has a patio, gazebo, and firepit.

LocationValueTV

Guest favourite

A well-maintained in-ground pool is shown surrounded by a concrete deck and lush greenery. A wooden fence encloses the yard, offering privacy. Tall trees and shrubs provide a natural backdrop, while the bright blue sky adds to the inviting atmosphere.

Home in Crystal Lake

4.98 out of 5 average rating, 45 reviews

Hot tub. Heated Pool. In town location.

In ground pool!! (Seasonal) Rent this entire home, experienced hosts, near town, 5 min drive to Crystal Lake main beach OR Three Oaks Beach/Recreation. Clean, Updated Home, with fenced in yard and pet friendly. 4 beds total (3 bedrooms) and 1 full bath. Fully stocked kitchen with all cooking supplies that you need. Hot tub. Basketball hoop in driveway, bags set in yard, great summertime home! Walk to Marianos/CVS/Walgreens, near it all!

LocationFamilyBathroom

Top Guest favourite

A spacious deck features a sectional sofa facing the sun setting over the Fox River. The area is surrounded by trees, providing a serene atmosphere. The deck's railing outlines the space while allowing unobstructed views of the water and landscape.

Home in Barrington

4.99 out of 5 average rating, 84 reviews

Barrington River Estate | Perfect for Groups

Watch as the sun sets over the Fox River from the spacious deck of this 4-bedroom, 3.5-bathroom vacation rental each night. This fully-equipped home has it all: kayaks, scooters, board games -- 3 bedrooms upstairs and lower level basement with full bathroom. Includes private beach access (100 yards away), kayaks, a fire pit, and a massive riverfront deck. Minutes to downtown Barrington venues and shops!

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Top Guest favourite

A circular fire pit area features six Adirondack chairs arranged around it on a grassy lawn. Lush trees provide shade in the background, while a covered porch of the Carriage House is visible in the distance.

Home in Elgin

4.96 out of 5 average rating, 70 reviews

Family/Pet Friendly Farm House w Firepit Sleeps 10

Welcome to the Carriage House, a quiet retreat on a small working farmstead. The home features generous living spaces, a fully equipped kitchen, and family-friendly amenities, including a fire pit for star gazing. Pets are welcome! Conveniently located just 1 hour from Chicago and 30 minutes from O'Hare. A security deposit and rental agreement are required. We look forward to hosting you!

LocationFamilyQuiet