Vacation rentals in Grayslake

4.8 out of 5 average rating, 106 reviews

A shaded gathering area is highlighted by wooden pergolas and several picnic tables beneath. A paved path leads to the space, flanked by decorative plants and tree plantings. Nearby, a brick wall adds texture to the setting, with blue skies and scattered clouds overhead.

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

A colorful array of flowers and greenery line the stone seawall along the lakefront. A paved pathway leads to a dining area with black metal chairs under a large umbrella, inviting relaxation by the water's edge.

Home in Grayslake

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

A wooden-framed sign is displayed on a light-colored wall, featuring the text 'WELCOME TO B'S FARMHOUSE COTTAGE' in an inviting, hand-drawn style. The design conveys a friendly welcome to guests arriving at the property.

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.

4.89 out of 5 average rating, 200 reviews

The sleeping area features a white iron bed frame with layered bedding, including decorative pillows. A wall-mounted TV is visible above a wooden dresser, and natural light enters through multiple windows with wooden blinds. A cozy seating area is provided by a basket and chair beside the door.

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

The spacious master bathroom features a two-person jacuzzi tub and a separate walk-in shower. Natural light is provided by large windows, enhancing the warm wood cabinetry and neutral stone surfaces. Fluffy towels are neatly arranged alongside personal care items on the countertop.

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

The exterior of the home features light-colored siding and red shutters, complemented by neatly trimmed shrubs. A stone pathway leads to a white front door, flanked by large windows that allow for ample natural light. Lush green grass surrounds the entrance.

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.

4.92 out of 5 average rating, 114 reviews

The exterior of the cozy cottage is highlighted by a blue facade, featuring a charming bay window with a small table and chair set in front. Lush greenery and garden beds add vibrancy to the entrance, creating a welcoming environment.

Cottage in Fox Lake

Cozy Cottage with Bedroom Lake Views!

Located on a hilltop peninsula overlooking Fox and Nippersink Lakes, Cozy Cottage is a 630 sq ft, 2 bed / 1 bath recently updated home with a large backyard — perfect for relaxing. You'll be conveniently located a 5 minute walk from waterfront bars and restaurants and have close driving proximity to: Downtown Fox Lake / Metra Station - 5 min Lake Geneva - 30 min Six Flags Great America - 30 min Illinois Beach State Park - 40 min Want to stay in? Our high speed wifi has you covered.

4.9 out of 5 average rating, 146 reviews

Home in Ingleside

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

4.89 out of 5 average rating, 208 reviews

Large windows provide a panoramic view of the lake, allowing natural light to fill the room. A ceiling fan hangs above, and a door offers access to the outdoors. An area for seating is visible, complemented by a refreshing beverage on a nearby surface.

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.

4.99 out of 5 average rating, 150 reviews

A cozy seating area features a gray sofa and a small table with decorative items. Natural wood walls add warmth, while large sliding glass doors frame the serene lake view, leading to an outdoor deck overlooking the water.

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

A charming bungalow exterior presents a warm facade with well-maintained landscaping. Features include a welcoming front staircase with wrought iron railings, potted flowers under large windows, and a flag hanging from the porch. A lush green lawn surrounds the home, enhancing its inviting presence.

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.

4.96 out of 5 average rating, 55 reviews

A modern living area is captured, featuring a large sectional sofa arranged around a circular coffee table. A textured area rug covers the floor, and natural light fills the space from the multiple windows. A ceiling fan and a wall-mounted television add functionality, while decorative elements enhance the cozy ambiance.

Apartment in Grayslake

Apartment in Downtown Grayslake

Welcome to downtown Grayslake! Enjoy your stay in our quaint one-bedroom apartment overlooking Center Street. Nestled above our lifestyle boutique, 27 Houses, you can enjoy everything our adorable town has to offer. Grayslake is practically straight out of a Hallmark movie, and you'll be right in the center of everything. With a cozy floorpan, enjoy a cup of coffee, listen to some vinyl, or get right to work at our dedicated workspace. We're excited to welcome you!

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Popular amenities for Grayslake vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Grayslake

5 out of 5 average rating, 22 reviews

A screened-in porch features a seating arrangement with plush chairs and a central table. Natural light streams through the screens, offering views of the serene lake and surrounding landscape. A ceiling fan hangs above, providing a comfortable breeze in the inviting space.

Home in Castle Manor

2BR Lake House | Lake Toys | Views | Dog Friendly

MagenRating, 5 stars2 weeks ago

We had the pleasure of staying here over our anniversary weekend with our 2 kiddos; it was our first vacation just our little family and it's was fantastic. Cristle was so helpful and went above and beyond to help us out when we had some issues on our end leading up to our trip. She was very thoughtful and kind and that alone was worth the 5 star rating. The home was very well kept and clean and had everything we needed for a nice relaxing weekend. We had a lot of fun out on the paddle boat and playing in the yard. The screened in porch was also a nice bonus. Our girls enjoyed the park and playing the sand. Overall it was a very nice stay and we'd love to go back sometime soon.

4.95 out of 5 average rating, 182 reviews

A bright living area is displayed with large skylights allowing natural light to fill the space. Cozy seating options, including a green sofa and orange poufs, complement a wooden coffee table adorned with books. Views of a snowy river and surrounding trees create a serene backdrop.

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, 38 reviews

An outdoor deck overlooks the lake, featuring a small glass table surrounded by two comfortable armchairs with light cushions. Lush greenery and trees frame the view, while the tranquil water reflects the sky.

Home in Castle Manor

Lake House- Private Frontage/Pier- Kayaks Included

KatieRating, 5 stars4 days ago

The home was comfortable, clean and well-stocked with cleaning and kitchen supplies. We relaxed and enjoyed the lake views, caught some fish from the dock, went kayaking, enjoyed s'mores, read and lounged in the patio areas, and kids had fun on the play set. Nearby, we enjoyed swimming at the beaches at Silver Lake and Lake Mary. Walked the neighborhood - lots of friendly neighbors. And, lots of tasty local food - Bodi's, New Taste of Italy, Dini's, and Sandlots. Highly recommend!

4.85 out of 5 average rating, 71 reviews

A long, silver-colored dock extends over calm water, leading towards the horizon. A clear blue sky with wispy clouds is visible above, and the shoreline features a mix of greenery and distant buildings, enhancing the lakeside setting.

Cabin in Pistakee Lake

Cozy Brick House Chain O'Lakes

LisaRating, 5 stars2 weeks ago

Absolutely loved this Lake House. My Husband and I had a great getaway. House is spotless and had everything we needed. Loved that Dockers restaurant and the Coffee house was right on the corner and a very short walk. Also loved that we could walk to Downtown Fox Lake and check all the places out. Great how close Lake was to house for lots of fishing. Had a great time and we hope to come back.

5 out of 5 average rating, 19 reviews

A clean bathroom features a modern vanity with a sleek sink and dark cabinetry. A spacious shower is visible, accompanied by a bathtub. The wall is adorned with colorful mosaic tiles, adding visual interest. A bottle of shampoo sits on the counter, providing convenience.

Apartment in Kenosha

Blue Sky Landing

JaneRating, 5 stars6 days ago

The location is a couple blocks away from Kennedy Park and beautiful Lake Michigan. We came for our granddaughters 1st birthday the Airbnb was close to my son's house. The Airbnb was one room. it had a microwave, refrigerator and toaster. The coffee machine was interesting and worked great. It also dispensed cold water.There was a closet. The sink was in the bathroom. The bathroom shower worked well, water temp and pressure good. Internet worked well. Lisa was very responsive and kind. We will visit Kenosha again and would definitely stay there again!

5 out of 5 average rating, 6 reviews

A modern kitchen features white cabinetry, a large island with seating for two, and stainless steel appliances. A decorative light fixture hangs above the island, while a window allows natural light to brighten the space. A vase with flowers adds a touch of color to the countertop.

Home in Crystal Lake

In Ground Pool, Full Ranch Home

MarkRating, 5 stars6 days ago

Great place and easy to work with.

4.97 out of 5 average rating, 33 reviews

Cabin in Bloomfield

Modern A-Frame Lake Cabin w/ Pickleball Ct.4Bd 3Ba

LaurenRating, 5 stars3 weeks ago

Tibi was the most incredible host for our Bachelorette party in Lake Geneva! The house was beyond beautiful and exactly as Tibi had described. We reached out to Tibi a few times before our official trip and always received a response within the hour - when we told Tibi we were going to do a wine tasting one night at the cabin she shipped in new wine glasses for us to ensure we had enough! As we are local to Chicago we will be keeping Tibi's Cabin in mind for any future trips as it was the perfect distance for a quick get away from the city!