Pet-friendly holiday rentals in McHenry County

Curated Loft Retreat in The Heart Of Woodstock

Welcome to our spacious upper retreat with modern conveniences. We have great WiFi for you to stay in touch with and are well stocked with books for you to enjoy time unplugged. Close to the Historic Square (you may have seen it in the movie Groundhog Day) you can easily walk to unique shops, cafes, and restaurants. Our curated timeless decor is filled with storied items from our travels, and photos we've snapped locally. Come renew yourself here. We can't wait to share Woodstock IL with you.

Villetta Bogdano

WRITERS ROOM A Romantic Tuscan-Inspired Hideaway in a Countryside Dream Welcome to your own private slice of countryside paradise—a soulful one-bedroom retreat that feels as though it was plucked from the heart of Tuscany and among lavender. This enchanting sanctuary is designed for those who crave peace, and a deeper connection to nature. Tucked away from the world, the cottage offers complete privacy with just birdsong in the morning, the bleating of goats, the soft cluck of chickens nearby.

Grand 1800s Victorian Gem: Updated/by Downtown

Step back in time with this Victorian, pet friendly, home featuring original pocket doors, gorgeous inlaid floors, & sparkling leaded glass windows. You will feel right at home with the comfort of the updated kitchen and baths with tons of space for all sized groups. This home is just three blocks from downtown Woodstock where you can dine, shop, & visit the famous opera house. Don't forget to visit the many scenes the movie Groundhog Day was filmed at throughout town and toast to world peace!

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 !

Heart of the Fox Riverhouse

Welcome to your perfect waterfront escape. This riverhouse blends indoor comfort with outdoor luxury—featuring a private hot tub, dock, and al fresco dining. Set right on the river with easy access to the lake, it’s ideal for peaceful mornings, great fishing, or tying up your boat after a day on the water. Explore nearby restaurants, golf, comedy clubs, and outdoor movies—or stay in and soak up the view. Whether you’re here to unwind or seek adventure, your getaway starts here.

The Cozy Lake House/Perfect Lake Front Getaway!

Welcome to The Cozy Lake House, your year-round haven for relaxation and celebration! Savor breathtaking sunsets, indulge in boating, watersports, and high-speed internet, and make special memories during holidays, bachelorette party's getaways, birthdays, family reunions, micro weddings, and more. With a fully equipped kitchen, spacious rooms, and the tranquil lakeside setting, every moment here is magical. Reserve your spot now and experience the ultimate in lakeside living!

Spacious Ranch blocks away from Downtown McHenry

Spacious 2 bedroom 2.5 bath ranch walking distance to downtown McHenry and the beautiful McHenry riverwalk. Located on McHenry Country Club this unique location is a peaceful getaway. Take advantage of the 4 season room and enjoy the tranquility of the lush green course as golfers enjoy a relaxing round. *Please contact host about golf options* Indoors you will find a 65 inch smart TV equipped with YouTube TV and an indoor jacuzzi located in the master bath.

Eden Farm: Family Stays & Intimate Moments

Unwind and find your inspiration just 1.5 hours from Chicago at our Elite Farm Retreat. Designed for executives, families, and intimate weddings. High-speed Wi-Fi, Smart TVs, and workspaces enhance your stay. This 5,000 sq ft estate blends modern comfort with rustic charm on 10 peaceful acres near Lake Geneva. Luxurious bedrooms, a Jacuzzi, and premium entertainment await. Two outdoor cameras monitor the front yard and driveway. No indoor cameras. Book now.

Elegant New Home Near Lakes - Relax & Unwind!

Welcome to your perfect getaway in Wonder Lake, IL! Nestled in a beautiful new community, our brand-new construction home offers the ultimate blend of comfort and convenience. Whether you’re here to relax by the serene lakes, coming in for work, explore picturesque walking paths, or take a short 20-minute drive to the stunning Lake Geneva, our home is the ideal base for your adventures. PLEASE NOTE CONSTRUCTION IS STILL ONGOING IN THE SURROUNDING HOMES!