Grayslake Holiday Houses

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Our top choices for Grayslake holiday homes

A two-story house with a stone chimney, a front porch with steps, and a flag.

1. Quaint Bungalow, near Great Lakes Naval Base

Mundelein

Jaclyn Z.

includes taxes & fees

30 Sept - 1 Oct

An outdoor patio with a hot tub, wicker chairs, and a table.

2. Hot Tub Retreats

Lake Villa

Rosilynn B.

includes taxes & fees

20 Sept - 21 Sept

A modern living room with a sofa set, a dining table with placemats, a coffee table, and a television.

3. 6 Beds Ideal for Crews & Insurance I Close to Naval Base and 6 flags

Waukegan

includes taxes & fees

22 Sept - 23 Sept

A modern house with a covered porch, large windows, and a well-maintained garden with various plants and flowers.

4. Master qtr close to nature & easy urban facilities

Riverwoods

Chris F.

includes taxes & fees

30 Sept - 1 Oct

A house by a lake with docked boats and a flag.

5. This is a VACATION spot with a million dollar view!

fox lake

Jason C.

includes taxes & fees

28 Sept - 29 Sept

A modern kitchen with white cabinets, stainless steel appliances, a large window, and a bar stool.

6. King bed Crystal Lake Mchenry Cary Cozy

Cary

includes taxes & fees

27 Sept - 28 Sept

A modern living room with a grey sofa, a grey ottoman, and a coffee table. There are large windows with curtains, a flat-screen TV mounted on the wall, and decorative wall art.

7. Navy Graduation ~ 6 Flags ~ Bristol Renaissance Faire ~ Casino ~ Outlet Malls

Gurnee

Jim L.

includes taxes & fees

13 Oct - 14 Oct

8. Modern 3-bedroom house in tranquil North Chicago near Great Lakes Navy Base

North Chicago

"Rented this property for my sons navy graduation, Base was only 6 minutes from the home. Tons of places to eat and shop no more then 15 minutes away. The house was super cute, very clean. we flew in at 10am and without even having to ask the host reached out and let us know it was ready for check in a few hours early which was great. left some packaged up congrats grad decor that hopefully didnt get thrown out and the next navy fam can use. "

Linda U.

includes taxes & fees

18 Oct - 19 Oct

A kitchen with a dark wooden table, white cabinets, and a sliding barn door.

9. Terrific 3-bedroom family-friendly house close to everything in charming McHenry

McHenry

Cj D.

includes taxes & fees

23 Sept - 24 Sept

A wooden deck with a table and chairs, surrounded by lush greenery and trees.

10. Spacious 3 Bedroom

Cary

Dan K.

includes taxes & fees

13 Oct - 14 Oct

A dining area with a wooden table set for four, a kitchen with white cabinets, and a living area with a sofa and chairs.

11. Great America Getaway | Sleeps 12 | Near Navy Base

Gurnee

Jack E.

includes taxes & fees

21 Sept - 22 Sept

A spacious living room with a wooden floor, a dining area, and a kitchen in the background.

12. Salem Vacation Home w/ Dock: Steps to Paddock Lake

Salem

Shanna D.

includes taxes & fees

18 Sept - 19 Sept

A modern living space with a kitchen, dining area, and a cozy seating area.

13. Charming 2-bedroom Channel house and kayaks in Paddock Lake

Salem

Rod L.

includes taxes & fees

1 Oct - 2 Oct

A kitchen with wooden cabinets, a black countertop, and a window.

14. Beautiful and Cozy With 5 Bedrooms

Zion

randy w.

includes taxes & fees

22 Sept - 23 Sept

A white house with a porch and a chimney, surrounded by a grassy area and a brick path.

15. The Tailor House

Woodstock

Brittany H.

includes taxes & fees

22 Sept - 23 Sept

A kitchen with a window, white cabinets, and a marble countertop.

16. Waterfront - Private Dock - Two Suites

Algonquin

includes taxes & fees

22 Sept - 23 Sept

A two-story house with a swimming pool, outdoor seating, and a stone chimney.

17. HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub

McHenry

"We stayed with our wedding bridal party here, and this massive and beautiful house was the perfect location to spend the weekend with all of our best friends! The house is obviously gorgeous, and the pool, hot tub, fire pit and pool table added an extra tier of fun. We hosted our rehearsal dinner on the back lawn and rented tables and chairs through the property, which was incredibly convenient.The property managers were communicative and very helpful throughout the process. I highly...

Brittany B.

includes taxes & fees

18 Sept - 19 Sept