Holiday rentals with a pool in McHenry County

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!

BRAND NEW 3 Bedrooms, Grill, 70 inch TV, KING Bed!

Note before booking: This home really is brand new! We are anticipating window treatments / shades and washer dryer to be installed the last week of December 2025. 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, comfortable retreat awaits!

Highwood Haven/Indoor Pool/Hot Tub/Arcade

Unwind at Highwood Haven, an opulent McHenry getaway with a heated indoor pool and arcade. Savor culinary delights in our chef's kitchen, enjoy al fresco entertainment, and relax in sumptuous bedrooms. An hour from Chicago, it's ideal for luxury retreats and family fun. Revel in our nine-person hot tub, outdoor lounge with TV, and serene bedrooms. Make memories with both lively entertainment and tranquil moments, all within a luxurious setting. Your perfect destination for an upscale vacation.

Couples Getaway! Hot Tub, Lake, Fire Pit, Trails

Private entrance to a stunning master suite.A VERY unique property.Sliding suite door opens to screened in pool room. Hot tub all year overlooking my private lake. Pool closed Oct. 1st. Seating area & TV to watch while lounging & swimming. (2) Kayaks 4 you. Walking & bike trails. I am minutes from everything U want. Grill, have a fire in the fireplace&fire pit.Bring your fishing poles! Time 2 RELAX in privacy. When not traveling, I live in main part of home. You won’t see me. No extra guests.

In Ground Pool, Full Ranch Home

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! As of 10/20/2025, pool will be closed for the season!

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 ..

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. *New third bathroom just added 3/01/25*

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.

Rustic Cabin

Our cozy cabins are comfortable, clean and equipped with A/C (or space heater!) Watch the world go by on the patio swing!

Beautiful 2 floor townhouse.

Very desirable area with ample space. Great for travelers, family vacation and personal travel.