Vacation rentals in Grayslake

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Top-rated vacation rentals in Grayslake

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Guest favourite

Condo in Kenosha

4.93 out of 5 average rating, 172 reviews

Inviting, spacious apt! Ideal for stay & work

This brand new basement apartment is an amazingly pleasant, spacious and private unit (over 950 sq. ft). Whatever the motive of your trip is —work from home, business, family function, wedding, graduation, friends, or simply a vacation escapade — you will enjoy the freedom this space provides. This residential, private neighborhood apartment is carefully designed. The full kitchen, classy bathroom, plush and extra-comfortable king size bed, the TV and all the amenities will fulfill your needs.

Jul. 21 – 28

$151 CAD per night

Guest favourite

Home in Beach Park

4.98 out of 5 average rating, 161 reviews

B’s Farmhouse Cottage 2-bedroom duplex.

Experience the best of the midwest! Enjoy a newly remodeled "Magnolia Farm" inspired 2-bedroom duplex, all to yourself near everything you need. 50 Miles from Milwaukee, miles from Chicago, and 2 miles having your toes in the sand at Lake Michigan. We are minutes away from the Great Lakes Naval Station and the Cancer Treatment Center of America, Six Flags Great America, Gurnee Mills, and Great Wolf Lodge. Whatever brings you here make J&B's Farmhouse Cottage your home away from home today.

Jan. 12 – 19

$215 CAD per night

Guest favourite

Cottage in Lake Villa

4.82 out of 5 average rating, 150 reviews

Laura’s Little Cottage

First, I’d like to mention this is located in a QUIET neighborhood. I don't rent out for big, loud parties. If that's what you're looking for, this is not the place for you. I like to keep peace with the neighbors! Moving on. This little cottage is just minutes from several forest preserves, the Chain O’ Lakes, Great America or Wilmot Mountain. 30 minutes to Great Lakes Naval Base & less than an hour to Lake Geneva, Chicago or Milwaukee. Plenty of restaurants, & grocery stores. 30 day minimum

May 11 – 18

$213 CAD per night

Guest favourite

Cottage in Libertyville

5.0 out of 5 average rating, 23 reviews

Woodland Guest House-Vintage Libertyville Chicago

The Woodland Guest House is uniquely located within a forest setting, and on a major road a 10-minute drive to downtown Libertyville and the Chicago train line. The modern apartment suite has four rooms, and was built onto an adjacent 1908 farmhouse. It combines peaceful silence with modern amenities, and is full of character. On three acres of oak savannah and trails, it is a certified Open Lands Property. Come to explore this exciting area, while staying in a charming forest suite!

Oct. 4 – 11

$120 CAD per night

Guest favourite

Apartment in Libertyville

4.91 out of 5 average rating, 43 reviews

528 Bungaloo 1 | 1 Bedroom | 1 Bath | Sleeps 2-4

May 30 – Jun. 6

$236 CAD per night

Guest favourite

Home in Grayslake

5.0 out of 5 average rating, 42 reviews

Adorable 2-bedroom home near downtown Grayslake!

Welcome to Mellow Yellow, an adorable home with everything you need. Located close to downtown Grayslake where you will find restaurants, bars and cute hometown stores. Walk to Jones Island to relax on the beach or head to the Aquatic Family Center for a dip in the pool. Six Flags Great America is just 7 miles away, Great Lakes Naval Base 13 miles, Gurnee Mills Mall 7 miles away or spend the day in Chicago which is 29 miles. Check out my guidebook for places to eat and visit!

May 13 – 20

$288 CAD per night

Guest favourite

Guesthouse in McHenry

4.95 out of 5 average rating, 155 reviews

"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.

Feb. 23 – Mar. 2

$203 CAD per night

Guest favourite

Apartment in Libertyville

4.91 out of 5 average rating, 85 reviews

131 East Park Ave. #308

Keep it simple at this peaceful and centrally-located apartment walking distance to fantastic downtown Libertyville. Very nicely maintained building with elevator. 7 miles to Great Lakes Naval Base. Super clean unit with all brand new furnishings. HD smart TV's with cable in both the living room and bedroom. Pull out bed in living room good for one person. Fast Wi-Fi with dedicated work desk. Ample free parking right in front of the building. On-site laundry one floor down.

Sep. 25 – Oct. 2

$152 CAD per night

Guest favourite

Home in Ingleside

4.93 out of 5 average rating, 110 reviews

Gorgeous Nautical 2/2 Lake House Chain O' Lakes

Unique and cute 2 bed / 2 bath nautical lake house has the best views of the Chain O' Lakes. Be amazed on the walk out lake view wood deck in the back yard, and watch sunsets fall over the bay and color the sky. The back patio is a great place to relax, entertain & relax. Fish or dock your watercraft at our pier if needed. There is an optional 5-6 person hot tub on the back deck for you to relax and unwind (See access and maintenance fee). Fully remodeled modern lake house

Sep. 18 – 25

$329 CAD per night

Guest favourite

Home in Round Lake Beach

4.89 out of 5 average rating, 148 reviews

Corner Lakefront Property

This unique place has a style all its own. This corner lake house comes with a huge fenced-in yard, as well as a balcony off of the master bedroom and 2 parking spots. We offer 3 kayaks with life jackets, 1 paddle board, paddle boat and fishing poles, fire pit, outdoor and indoor games. We have 3 bedrooms with beds included, as well as a futon couch a trundle bed and a pull-out couch bed (6 potential beds total). This comes with 2 TVs, fireplace, WiFi, bar, new fridge and more.

Feb. 18 – 25

$351 CAD per night

Guest favourite

Home in Round Lake Beach

4.99 out of 5 average rating, 99 reviews

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!

Dec. 1 – 6

$289 CAD per night

Guest favourite

Bungalow in Mundelein

4.87 out of 5 average rating, 183 reviews

Quaint Bungalow, near Great Lakes Naval Base

This cozy bungalow is located 41 miles north of Chicago; 60 miles south of Milwaukee, WI; and just 12 miles west of Great Lakes Naval Base. Nearby train stations make Chicago just a 45-minute train ride away. O'Hare Airport is a 30-40 minute commute from our home. Additional nearby sites include Great America, and shopping venues--from outlet malls in Gurnee and Kenosha, to quaint downtowns, like Libertyville. Location makes this home an ideal venue for Midwest sightseeing.

Aug. 23 – 30

$234 CAD per night