Pet-friendly vacation rentals in Grayslake

Cozy 2-Bedroom Cottage Near Downtown Highland Park

Step into a warm, inviting retreat where comfort meets character! This beautifully updated suite features two cozy bedrooms, a private bathroom, and thoughtfully decorated living spaces in a modern farmhouse style. Nestled in the heart of Highland Park, you’re steps from great restaurants, boutique shops, scenic trails, and parks, plus a golf course across the street and just 1.5 miles from Lake Michigan. Whether it’s a family getaway or a business trip, it’s your perfect home away from home!

Outdoor spaces · Walkability · Sleep quality

#4: Cute 2 bedroom cottage on the beach!

Relax & make lasting memories at this peaceful 2-bedroom cottage at Turtle Beach Marina. Enjoy the sandy beach on the lake, rent a boat or kayak, & unwind with summer drinks at the beach bar. A restaurant & game room (slots) are right on the property. (Bar & slots open mid-May through October.) Celebrating something special? Add a $75 package: 🌹Romantic Package: rose petals, candles, wine, & chocolates. 🎂 Birthday Package: HBD banner, balloons, 10-inch cake, & candles. Let us know in advance!

Pets · Outdoor spaces · Grill

Enjoy a Getaway @ The Lake-Heim by Chain-O-Lakes

Enjoy a comfy retreat in this cute 1BR home nestled right next to Grass Lake, IL. Newly updated shower. A lovely space to unwind by the lake whether it is work or play. Awake to a quiet morning, ready for a day of water activities with impressive views. Early risers can catch a sunrise to die for. Indulge in the comfort and tranquility of this lakehouse cabin. We conduct regular pest treatment to keep pests away, but being close to nature and the lake, expect occasional bugs in warmer weather.

Outdoor spaces · Pets · Hospitality

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!

Pets · Outdoor spaces · Check-in

TheGlassCabin @ HackmatackRetreat

The Pond House, a vintage glass cabin filled with art, water views & eclectic vibes privately perched on the sacred grounds of Hackmatack Retreat Center. Native prairie, a winding slow river, two ponds, 200+ year old oaks & big sky- Countless places to curl up, gathering, focus-- nooks and crannies indoors and out, we offer “time out for time in” amidst this noisy world. Minutes from 2 small towns, all amenities, we're all about peace & ease-- let us custom curate your experience !

Outdoor spaces · Pets · Location

Your relaxing stay in Highland Park

Whether you are looking to escape the city hustle and bustle, visiting Lake Forest College, the Naval Station or moving cross country, our bright and spacious suite is the perfect spot to check in and relax for a few nights. Featuring a separate entrance and a beautiful, private newly remodeled bathroom. 43 4K Smart HDTV with Netflix and Prime and super fast WiFi available for streaming. Kitchenette with a microwave, mini fridge, sink and cups/plates/010/053/2026cutlery.

Walkability · Pets · Value

Cozy mother inlaw suite. Private. Next to beach.

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.

Walkability · Outdoor spaces · Heating

Lovely top floor 2BR/2BA, steps from everything!

BEST LOCATION IN LOGAN SQUARE/AVONDALE! Brand new stylish TOP floor 2 bed/2 bath located in the heart of the highly desirable Avondale neighborhood. This luxurious space is situated 15 minutes drive to Wrigley Field, 7 minutes walk from the CTA Belmont Blue Line, only minutes away from O'Hare airport, downtown Chicago and The Loop. Conveniently close to expressway. Steps from award winning restaurants, popular bars, great coffee shops, clubs, galleries and exclusive shops.

Pets · Walkability · Bathroom

"A" Frame Brandenburg Lake

Getaway to a cozy 1 bedroom w/loft for 2, up to 6 people. Full kitchen 1.5 bath all season getaway. There is a piano as well. A tranquil home steps from a private lake. Oak and Pine surround you plus a stone fireplace, it feels like the North Woods. The A Frame guest house shares a 5 acre compound ( total 20 Acres) with the owners residence and caretaker cottage. The Volo Bog 800ft away. No hot tub Nov - May. Swimming pool, June-October often cool to use in early June.

Walkability · Pets · Amenities

Spacious 2-br, 1 bath home w/AC near Naval Base

Welcome to our cozy and comfortable Airbnb, perfectly located near Naval Station Great Lakes (approximately 5-7 min., 2 miles), Six Flags Great America, and just an hour from downtown Chicago! Whether you're visiting for Navy graduation, family time, business, or a weekend getaway, our home offers the perfect balance of convenience and relaxation. We take pride in providing excellent hospitality and a smooth, stress-free experience from check in to check out.

Walkability · Outdoor spaces · Comfort

Lake house Monica Steps from the lake! 4BD 3bath

4BR/ 2.5Ba 3000ft2 Fun Lake house Monica at Duck Lake Lake front house, back your great for fire pit. Large Porch whit barbecue. Fire place, 75inch TV, internet, 4 great bedrooms additional bathroom in the basement, 2,5 bath, laundry room, games room: pool table, pingpong table, darts, soccer game, full kitchen, 6 parking space + 2 garage space, 2 bikes, 6 kayaks, private lot . Romantic and Family friendly. Brand new steam sauna.

Pets · Outdoor spaces · Accuracy

Historic Downtown Libertyville Loft

Enjoy a stylish experience at this centrally-located 1600 square foot place. Located in the heart of Downtown Libertyville, half way between Chicago and Milwaukee. Close to Six Flags, Great Lakes Navy Base, Lake Michigan beaches, forest preserves, train station and the Chain of Lakes. Downtown Libertyville is a trendy town offering several restaurants, shops and fun events. Book one of the only units truly Downtown Libertyville.

Pets · Walkability · Layout