Vacation 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.

Walk to downtown McHenry. Heart of the Fox River

NO PETS Entire 2nd. floor. 1 block away from downtown, Fox River Riverwalk & Pokémon Gym. Full stocked kitchen, books, games, toys & extra amenities to make your stay beyond relaxing. 4:20 allowed in backyard & not in view of under the age of 21. Private smoking area in front too. Minutes away from 2 State Parks, 1 with free boat/kayak launch. Several marinas, boat rental, golf courses & huge variety of entertainment. Look at Bettye's Guidebook for more information & nearby entertainment.

Cabin on the Prairie

The historic 1830s log cabin, nestled within a healing and restorative prairie setting, is thoughtfully decorated with vintage furnishings to transport visitors back in time, yet fully equipped with modern amenities for a cozy and relaxing stay. Perfect for families, couples, or “me” time, the cabin is conveniently located between the historic communities of Woodstock, IL and Lake Geneva, WI, where there is something for everyone, with shopping, dining, culture, and adventure just minutes away.

Large Farmhouse Main Street Retreat

Charming Historic Apartment in Downtown Crystal Lake Spacious second-floor apartment overlooking Downtown Crystal Lake, located in a vintage 1875 farmhouse. Steps away from over 100 restaurants, shops, coffee spots, and bars, all within a 2-minute walk. Enjoy updated bedding, modern comforts, and vintage finishes in a quiet space with no shared walls or upstairs neighbors. One parking space included, with additional lot park CHECKOUT OUR OTHER PROPERTIES HERE: www.airbnb.com/p/breganproperties

Sanctuary Woodland Guest House!

Our guest house is located on a picturesque 5 acres, next to a woodland forest. We also run a bird sanctuary on the property, Georgia's Place Bird Sanctuary, which makes this a paradise for an animal lover! We are happy to give guests a tour of our sanctuary. There is a large deck and fire pit for an enjoyable evening, and a walking trail for wildlife enthusiasts! We kindly ask guests not to bring meat onto the property as we are running a sanctuary that promotes compassion for all animals.

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. 🏡

3 Bedrooms, 2.5 bath, 70 inch TV, *KING Bed*!

Note before booking: We are anticipating the final window shades to primary bedroom to be installed first week of 2026. There is ongoing construction in the community. The Wonder: A Brand-NEW 3BR, 2.5BA townhome in the private Stonewater Community! Peaceful, pet-friendly, and perfectly located near McHenry, Wonder Lake, and Woodstock with easy access to Chicago. Sleeps 8, features a 2-car garage, baby gates, and summer pool access. On-site gym coming soon. Your modern retreat awaits!

Waterfront Stay w/ Walk to Downtown Entertainment

Apartment overlooking the Fox River. Walking distance to downtown Algonquin. Free 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. You'll be able to relax, get a restful sleep, and enjoy your visit. You'll also notice the little touches and the extra effort made to assure you have an awesome stay. Private Bathroom and Kitchen.

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 !

"The Apartment" in the heart of downtown McHenry

We welcome you to be our guest in this charming, historic home built in 1911 by a German mason. This upper unit Apartment is a spacious 1,100 square feet, lovingly restored with a vintage aesthetic in 2018. The private entrance to "The Apartment" will lead you to; 2 cozy bedrooms & 1 vintage inspired yet modern bath with walk in shower. A large living room, dining area and bright clean kitchen will make you feel right at home. 9 foot ceilings and tons of natural light through out.

The Cozy Lake House, Dm me ?s Lake Front Property!

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!

Wonder Lake Elegance Home

Step into a world of peace at our Wonder Lake retreat, a 2-bedroom townhome where elegance meets serenity. Indulge in the contemporary comforts of our open-layout living space, featuring a state-of-the-art kitchen and an indulgent master suite. Beyond the walls, nature beckons with picturesque trails and a park that whispers tranquility. Ideal for both leisurely family escapes and productive retreats, our home is a gateway to local experiences and serene moments.