House holiday rentals in Lake in the Hills

Cozy 2-Bedroom Cottage Near Downtown Highland Park

Step into a warm, inviting retreat where comfort meets character! This beautifully updated suite features two cozy bedrooms, a private bathroom, and thoughtfully decorated living spaces in a modern farmhouse style. Nestled in the heart of Highland Park, you’re steps from great restaurants, boutique shops, scenic trails, and parks, plus a golf course across the street and just 1.5 miles from Lake Michigan. Whether it’s a family getaway or a business trip, it’s your perfect home away from home!

Dog Friendly Cozy North Naperville 3 BED/2 BA Home

Welcome to the Naperville Nest! Rare North Naperville opportunity to find a home suited for the whole family! Pets are more than welcome to enjoy the 1/2 acre fully fenced in yard. This is a a fully updated home minutes from Downtown Naperville, I-88 and many more exciting destinations in the Western Suburbs. You will feel at home whether you're inside or outside...each bedroom has it's own TV and the outdoor living includes natural gas firepit & grill/dining table...this home has it all!

Adorable 2-bedroom home near downtown Grayslake!

Welcome to Mellow Yellow, an adorable home with everything you need. Located close to downtown Grayslake where you will find restaurants, bars and cute hometown stores. Walk to Jones Island to relax on the beach or head to the Aquatic Family Center for a dip in the pool. Enjoy nearby attractions, Lake County Fairgrounds, Six Flags Great America, Great Lakes Naval Base, and Gurnee Mills Mall, or spend the day in Chicago which is 29 miles. Check out my guidebook for places to eat and visit!

3 BR near DT Woodstock Square | Hot Tub & Arcades

Welcome to Woodstock's Victorian Square! Embark on a delightful escape to the serene embrace of Woodstock's Victorian Square. Nestled on a peaceful street, this inviting haven offers a perfect blend of tranquility and convenience. Enjoy a quiet night's sleep and a short stroll (2 blocks) to discover the delights of coffee, chocolate, art, and antiques. Historical Charm, Modern Comfort: Immerse yourself in the allure of a completely renovated (2021) historic home, built in the 1920s. 🏡

The River House Sauna/Kayaks/Hot Tub/Fire Pit

The newly remodeled water front 4 bd 2 bath home is within walking distance of Algonquin’s fabulous "Old Town District", restaurants, pubs and entertainment. Likewise, the gorgeously landscaped River Park is a short stroll away, giving one much to see and do. The residence feature a beautiful kitchen; large dining area adjoins the kitchen as does a brightly sun shined living room complete with big glass doors overlooking the water. A picturesque living for both work and play awaits!

TheGlassCabin @ HackmatackRetreat

The Pond House, a vintage glass cabin filled with art, water views & eclectic vibes privately perched on the sacred grounds of Hackmatack Retreat Center. Native prairie, a winding slow river, two ponds, 200+ year old oaks & big sky- Countless places to curl up, gathering, focus-- nooks and crannies indoors and out, we offer “time out for time in” amidst this noisy world. Minutes from 2 small towns, all amenities, we're all about peace & ease-- let us custom curate your experience !

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!

Cozy Country Cottage near Lake Geneva, WI

Our Cozy Cottage features 3 comfortable bedrooms and nightly magnificent sunsets. Nestled on a country road, the house offers plenty of space to rest after visiting Lake Geneva, Lauderdale lakes, biking at Kettle Moraine or site seeing in the area. It’s close to Walworth County fair grounds where the flea market, Das Fest and Rib Fest are held. This is country living with plenty of opportunity to enjoy the beautiful outdoors or the peace and quiet of the countryside.

Hidden Gem Spanish Style Villa

Unique to Northern Illinois, this Spanish style Villa sleeps 10+ , boasts five patios, a Cantina, 7 ARCADES, HOT TUB, and many surprises you will find as you look at every turn to something unexpected. This property is filled with beautiful furnishings, featuring a balcony off of the upper level that boasts a 12 foot ceiling. Everything from two walk in showers, a jet tub and a hot tub for any level of self-care desired.

Lockports Famous Hideaway ~ 2bdrm Guest House Flat

A history buff’s dream filled with antiques & artifacts relating to Chicago, Joliet, Lockport, the I & M Canal & "Route 66"! Family & Business Friendly. The entire upstairs 1,500 sq ft vintage 2-bedroom house apartment is all your own space. The flat is NOT shared with other guests/host. Private-entrance/self-check-in. Have a 'historic' stay at the "Hideaway"! Can accommodate up to 6 guests.

Luxury Lakehouse 6 Bed with Private Pier

Escape to our 6-bedroom lakefront retreat with multiple kitchens and expansive living spaces, perfect for unforgettable group getaways. Wake up to stunning lake views from every bedroom. Soak under the stars in the hot tub, gather by the fire pit, or relax on the deck above the water. Ask about 2026 pontoon rentals with your booking!

The Retro Rectory

Retro decor, 3 bedrooms, 4 luxurious beds, fully equipped kitchen all available in this expertly styled home located in a walkable exurban city. Just 15 minutes from Lake Geneva, 45 minutes from Milwaukee, 90 minutes from downtown Chicago, and a short drive to several other interesting Wisconsin towns. NO CLEANING FEES