Holiday houses in Grayslake

4.8 out of 5 average rating, 106 reviews

Apartment in Grayslake

Historic home in quaint Grayslake, self check-in

Nestled in the heart of the historic village of Grayslake, this well-appointed flat, with brand new furnishings, linens, amenities, and a newly-renovated bathroom, is within easy walking distance to the restaurants, breweries, wine bars, coffee shops and the beautiful shoreline of Grayslake. Great Lakes Naval Base (11 miles), Six Flags, Fox lake, and other Chicagoland attractions are a short drive away. Multiple Metra lines to downtown Chicago and O'Hare are close. 10% Military family Discount.

5 out of 5 average rating, 29 reviews

Lake House Walk to Train-Chicago

Lake Front with stone seawall, fire pit and jacuzzi. Two fireplaces, one wood burning and one gas. Floor to ceiling windows showcasing sunsets over serene Grayslake. Two paddler boats for you to paddle to Jones Island beach and playground. A five-minute walk to downtown Grayslake which boasts 9+ restaurants, an outdoor fireplace, two wooded parks with paved paths. A five-minute walk from the house to the Metra train taking you to downtown Chicago, a 1 hour train ride. Minimum 3 nights.

4.98 out of 5 average rating, 222 reviews

Home in Beach Park

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.

4.98 out of 5 average rating, 87 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. Enjoy nearby attractions, Lake County Fairgrounds, Six Flags Great America, Great Lakes Naval Base, and Gurnee Mills Mall, or spend the day in Chicago which is 29 miles. Check out my guidebook for places to eat and visit!

4.89 out of 5 average rating, 200 reviews

Guest suite in Zion

Non-smoking, attached mother-in-law suite.

25 minutes away from the Naval Station 5 minutes away from the beach. 10 minutes to Wisconsin. 1 hour 40 minutes to O’Hare Airport and downtown Chicago. 40 minutes to Milwaukee Airport 25 minutes to Six Flags and Great Wolf Lodge. Safe and quiet neighborhood with plenty of wildlife right in the back yard. This Mother in Law suite has tons of natural light. For nature lover’s this unit is close to the beach and there are walking trails nearby. Small children maybe heard from 7AM to 7PM.

Guest suite in Riverwoods

4.96 out of 5 average rating, 400 reviews

Master qtr close to nature & easy urban facilities

This amazing prairie style home sits on 2 acre land surrounded by lush lawn and majestic oak trees - a nature lover's dream with unparalleled serenity. Vacation-like setting blends country-like quiet with nearby conveniences including shopping, trains, restaurants, highways, Ravinia (18 MINs drive). 5 MINs to I 294. 20 MINS to O'HARE; 5 Mins to Discover, Baxter; 10 MINs to Walgreens Deerfield campus, TRINITY INT'L UNIVERSITY; 15 MINS to Lake Forest Academy. 25 MINs to Great Lakes Navy Base.

4.99 out of 5 average rating, 659 reviews

Guest suite in Geneva

A Suite within a Cozy cottage in Geneva Illinois.

Cozy private suite in the lower level. Guests have the suite to themselves. The bathroom is adjacent to the room and is private. There is a small fridge, a coffee maker, and a microwave oven. We are in Geneva, Illinois. We are LGBTQ+friendly. Our space is ideal for shorter stays and visitors on the go . Not suitable for staycations. Quiet area. Hosts live on the upper level and guests pass through our space to get to the suite. In a bind we can accommodate a 3rd guest and a pet. Welcome.

Apartment in Libertyville

4.82 out of 5 average rating, 87 reviews

131 E. Park Ave - Unit 306

Keep it simple at this peaceful 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. There is a comfortable rollaway bed behind the couch that is perfect 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.

4.89 out of 5 average rating, 208 reviews

Home in Round Lake Beach

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.

4.71 out of 5 average rating, 28 reviews

Townhouse in Grayslake

Cozy suburban home near the Windy City of Chicago.

Comfortable and beautiful townhouse in Grayslake. Fully equipped kitchen, 1.5 bathrooms, 2 bedrooms, a living room, and a laundry room. Check yourself in with the smart lock. Perfect for remote domestic work with a fast internet connection of 400 Mbps, plus a dedicated workspace. Free driveway parking on premises - 2 spaces. Six Flags Great America is 6.6 miles away, Great Lakes Naval Base is 13.9 miles away, Gurnee Mills Mall is 6.2 miles away, and Chicago is 49.1 miles away.

4.99 out of 5 average rating, 150 reviews

Home in Round Lake Beach

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!

4.87 out of 5 average rating, 211 reviews

Bungalow in Mundelein

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.

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Other great holiday rentals in Grayslake

Home in Mundelein

4.67 out of 5 average rating, 15 reviews

Dreamy Private Lakehouse!

JeanRating, 5 stars1 month ago

This is a very spacious home and has many accommodations. Ream was always quick to response with an answer to our questions, whether it was before our stay or during are stay. We all enjoyed out stay there!

Private room in Crystal Lake

4.89 out of 5 average rating, 155 reviews

Master Bedroom w/Bathroom - safe and cozy

ReneRating, 5 stars1 week ago

This was my third stay - it’s an awesome place and I felt right at home. Highly recommend!

5 out of 5 average rating, 8 reviews

Historic Grayslake

KevinRating, 5 stars1 month ago

Jeff is an amazing host. He took the time and made extra effort for our stay when we brought our family to Illinois for my son‘s Boot Camp graduation. The home is absolutely amazing. It has everything you need. The location is easy to find the landscape is beautiful. I highly recommend this home to anybody staying in the area. Jeff went above and beyond for us and stating contact with us the entire stay to ensure our stay was fantastic. We had family come in from out of town from a couple of different states. This home was perfect to accommodate all of our needs.

5 out of 5 average rating, 5 reviews

Moss Point House-Newly Renovated

AlissaRating, 5 stars2 days ago

The house was decorated extremely well and was spotless. Kelly left us a thank you note and a jar of honey, that was a very nice touch. If we need a place to stay in the Grayslake area in the future, we will definitely be booking at this location again. Thanks Kelly!

4.95 out of 5 average rating, 182 reviews

Home in Richmond

TheGlassCabin@HackmatackRetreat

JayRating, 5 stars2 days ago

What a beautiful rustic setting. So many wonderful Buddhist / mindfulness reminders to disconnect and slow down. We would love to come back to this getaway location again!

5 out of 5 average rating, 12 reviews

Home in Gurnee

1/2 Acre Retreat: 100" TV, Open layout | Navy Base

MichelleRating, 5 stars1 week ago

The house was amazing we couldn’t have picked a better place to stay for my son’s Bootcamp graduation. Our guests really loved the house and how spacious it was. The master bathroom was breathtaking. All the beds in the house were comfortable and the bedrooms were big enough. The backyard was gorgeous the grass was beautifully green and the deck was perfect to sit outside in the morning drinking coffee. The location was perfect as well about 15mins from the base and 10mins or so driving distance to shopping and food.