Vacation rentals with a pool in McHenry County

Fabulous Cabin

WELCOME TO WATERFRONT LOG-SIDED HOME! ARTISAN CRAFTMANSHIP HOME OFFERS A BACKYARD OASIS SITUATED , NESTLED ON A PRIVATE POND, Heated POOL(closed till April 1st), Hot tub open from Oct 15th to Apr 15thGAZEBO, FIRE PIT, FISHING! 4 BEDROOMS AND 4.5 BATHS The homes sits on the highest point in the neighborhood and has stunning views in the front & backyard! Enjoy the mornings sitting on your front porch. The main floor is completed by an office, finished walkout basement in with a custom built bar

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!

It's 5'oclock somewhere

Stop. This is it. Stunning home, all the updates and a resort style backyard. Inground heated pool, hot tub, tiki bar, firepit and plenty of seating. Inground heated pool opens 4/10 for the season! Mstr Bdrm w/true mstr ste sitting area and wet bar. Mini fridge in room. Master bthrom has jacuzzi soaker. Sleep number king size bed. Fireplace in suite. 2 other bedrooms upstairs down the hall, bedroom2-queen bed with mini fridge and ceiling fan. bedroom3-bunk beds with closet and dresser.

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!

A get away with an indoor pool.

Thank you for considering our home! Enjoy your private oasis with a heated pool 80-84 degrees (year-round) perfect for relaxing and enjoying life. While all our guests were wonderful, we had an exception. Before booking, please note: Celebrations, Small gatherings only—no loud parties/proms. Accidents and Damage happen: please provide full list of anyone entering the home. We trust you will treat our home as your own. We hope your stay will be wonderful!

Stunning 6000sf LODGE on 3 acres in Spring Grove.

Come to the country and stay in this stunning 6000sf lodge on 3 plus private wooded acres, only 20 minutes to Lake Geneva and 7 minutes to Epic Wilmot ski Hill. This home boasts cozy and the feel of the outdoors, 2 fireplaces, huge basement with log bar and poker table, ping pong etc .2 outside fire pits boasts with gradure and space . Can fit a huge crowd of people .You won't be disappointed. Come to the Lodge and stay a while ..

Hot tub. Heated Pool. In town location.

In ground pool!! 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. Basketball hoop in driveway, bags set in yard, great summertime home! Walk to Marianos/CVS/Walgreens, near it all!

Crystal Lake Pool House with Sauna

Relax at this private Crystal Lake retreat featuring an indoor swimming pool and traditional sauna with a stone heater. Perfect for families and small groups looking for a peaceful getaway near Chicago. The home offers 3 bedrooms, 2 bathrooms, a fully equipped kitchen, and a spacious backyard with a grill area for outdoor cooking and relaxing. A great place to unwind, swim, and enjoy time together.

Pet friendly Rustic Cabin

These rustic (no bathroom) cabins are designed for guests, that like to bring their dog camping! There is a fenced-in area, that includes a large brick fire ring and one of our popular patio swings! The cabin is equipped with an a/c unit (or space heater when necessary), small refrigerator and parking space nearby. Bathrooms and showers are located in the nearby main building.

Deluxe Cabin with Loft

This beautiful cabin has a full bathroom, a separate master bedroom, a small bedroom with two twin bunks and a loft suitable for two children! Your outdoor space consists of a deck and a patio with a large brick fire ring, a propane grill and a patio swing! We also added a fenced in area for your dog to hang out while you are enjoying your patio!

Living the High Life Pool House

Relax with family & friends at our large heated indoor pool with a tiki bar, game room & stylish, cozy living space & kitchen. With tons of gathering space, you can enjoy our home in all seasons. *Hot tub added Feb 2nd*

Deluxe Studio

Come and camp in style! These small deluxe cabins are bright and very cozy. The queen bed is in the main room, while the (full sized) bunk beds are in a separate bedroom. Full bathroom and beautiful Patio with Swing.