Vacation rentals in Pistakee Highlands

Enjoy a Getaway @ The Lake-Heim by Chain-O-Lakes

Enjoy a comfy retreat in this cute 1BR home nestled right next to Grass Lake, IL. Newly updated shower. A lovely space to unwind by the lake whether it is work or play. Awake to a quiet morning, ready for a day of water activities with impressive views. Early risers can catch a sunrise to die for. Indulge in the comfort and tranquility of this lakehouse cabin. We conduct regular pest treatment to keep pests away, but being close to nature and the lake, expect occasional bugs in warmer weather.

Waterfront House, 2 kayaks, Game room, Fire pit, B

Escape to this stunning waterfront house in McHenry, Illinois, offering a perfect blend of relaxation and adventure. Enjoy kayaking on the waterway leading to Pistakee Lake, fishing from the private dock, or simply unwind in the hammock. This home features a sunroom with water views, a game room for entertainment, and a cozy fireplace. With a fully equipped kitchen, outdoor seating, and a BBQ grill, it's ideal for families and groups seeking both outdoor activities and comfortable and relaxing

Lakefront Cottage with Gorgeous Sunsets

Great cottage so close to the water you can fish right off the deck, bring your boat right up to the dock and drive it all over the chain of lakes and out to dinner. Endless things to do on the chain, tons of restaurants, sand bars, fishing, bars, boats, etc. Then, watch the sunset at the beach right outside your door before retreating for the night into the cottage. The yard is fenced in, with a fire pit and is shared with permeant residence and another house I air bnb but is yours to enjoy

Center Lake View Cottage, near Camp&Silver Lakes

Relax & enjoy your stay in this peaceful home in quiet, friendly neighborhood. Launch boat in Center Lake at end of street or several nearby lakes. Camp Lake is 2 mins away, close to Silver Lake and many others. This home has an awesome sled hill, fire pit with seating area, and a relaxing deck with lake views. Close to Lake Geneva, & Renaissance Faire. Ski at Alpine Valley or Wilmot Mountain. 25 mins to Six Flags or Lake Geneva, 1 hr to Chgo or Milwaukee. 35 mins to Great Lakes Naval Base.

Walk to downtown McHenry. Heart of the Fox River

NO PETS Entire 2nd. floor. < 2 blocks away from downtown, Fox River Riverwalk. Pokémon Gym across the street. 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. Minutes from 2 State Parks, 1 with free boat/kayak launch. Several marinas, boat rentals, golf courses & other varieties of entertainment. Look at Bettye's Guidebook for more information.

Nippersink Lakehouse-Private Pier & Pet friendly!

A perfect gateway home for the family or a small group. The beautiful sunset can be viewed from the raised deck or the private pier. There are 2 jet ski ramps and room for boat parking, so bring your water toys and enjoy this amazing boating vacation property. Nippersink lake is right in the middle of the 13 interconnected lakes that makes up the amazing chain of lakes. Enjoy fishing, utilizing the 4 provided kayaks or stand-up paddle boards upon request for unlimited water fun.

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.

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!

Wonderful Mineola Bay Lakefront Cottage 4adu+4kids

Book a romantic weekend or bring the whole family to this cozy, clean and well-appointed lake house that has plenty of room for fun. Embrace lake-life at its finest when you call this Fox Lake cottage on Mineola Bay your home away from home! We have a dock to park your boat, so bring it. Access to restaurants, bars, convenience and grocery stores, boat launches and more. Or hang out and soak in the sunshine while paddle boarding, boating, kayaking, swimming and nature hikes.

Waterfront Oasis w/ Hot Tub, Sauna, FirePit & Pier

Welcome to Whispering Willows Sanctuary, a rare and secluded wellness and waterfront escape nestled on Chain O' Lakes. Surrounded by water on two sides, this stunning 180° waterfront property offers a one-of-a-kind setting along a peaceful channel that flows directly out into the Fox River and Pistakee Lake. Anchored by a majestic weeping willow tree gently swaying over the shoreline, this property lives up to its name—offering a serene, private retreat.

Lakeside Getaway 1 Bedroom

Take a break and unwind at this peaceful oasis. The holiday home features lake views, air-conditioning, and a fully equipped kitchen with a refrigerator, microwave, dishwasher, oven, and stovetop. Additional amenities include a dining area, TV, and outdoor dining space. Not far from Chicago O'Hare International Airport (36 mi), Six Flags Great America (14 mi), Naval Training Center, Great Lakes (22 mi), and Raging Buffalo Snowboard Ski Park (23 mi).