Holiday rentals in Long Grove

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!

Walk to downtown McHenry. Heart of the Fox River

NO PETS Entire 2nd. floor. 1 block away from downtown, Fox River Riverwalk & Pokémon Gym. Full stocked kitchen, books, games, toys & extra amenities to make your stay beyond relaxing. 4:20 allowed in backyard & not in view of under the age of 21. Private smoking area in front too. Minutes away from 2 State Parks, 1 with free boat/kayak launch. Several marinas, boat rental, golf courses & huge variety of entertainment. Look at Bettye's Guidebook for more information & nearby entertainment.

Enchanted Garden Treehouse (Amenity*)

Spring is here, the flowers out, the treehouse warm and cozy, and the hot tub ready! Relax on cool evenings in our luxurious, very private, 4' deep cedar hot tub nestled in the evergreens, while the moon and stars swirl overhead, the waterfall cuts thru snow into the koi pond, and the fire table and torches blaze. The running stream makes this a wildlife refuge, with tons of birds, squirrels, rabbits, foxes and hawks. We are 420 friendly. Come experience the magic and make a special memory!

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.

Charming space w/ use of deck and yard

Charming home in Highland Park. The space is my in-law suite which is in the lower level of my home and has its own full size kitchen and bathroom. I live up-stairs with my 3 small dogs so I will be available if you need anything during your stay. The in-law suite is set up like a studio and has ONE queen bed, a separate closet area and laundry. Please note- the suite is in the basement (stairs), but there is natural light. You have use of the deck/yard if desired. No stays over 3 weeks.

Penthouse In The Historic Hobbs

Experience luxury and historic charm at the Penthouse in the Historic Hobbs. Built in 1892, and restored in 2023, this new one bedroom corner unit offers a panoramic view of the Aurora skyline. Cook a delicious meal in the fully stocked kitchen. Dine at the bespoke table in the window bay under the iconic onion dome. Relax on the cozy sofa and enjoy a movie on the big screen TV. Rest in the plush king-sized bed. This urban retreat is near coffee, shopping, art and entertainment.

3BR w/Escape Room*Foosball*AutoEspresso*CerealBar

This house is 3BR + sofa bed in the basement and 1.5bath with an in-home escape room-style game throughout the property. The patio transforms into a pickleball court, the game room offers arcade games & Nintendo Classic, and the garage adds foosball. Stocked kitchen with cereal bar. Outdoors, relax with a BBQ grill while kids enjoy the playground. Inside: cozy living room 55" TV, full kitchen w/cereal bar, automatic espresso machine & baby essentials (high chair, packNplay).

Beautiful 3 bdrm home, 20 min to Naval Base

Relax with the whole family at this peaceful place to stay. Quick 20min drive to Great Lakes Naval Base and 25mins to Great Wolf Lodge! This beautiful home is perfect for couples & families coming to Lake County to visit family or attend graduation from Great Lakes Naval Base. The renovated kitchen is well appointed, & in-unit laundry makes you feel right at home! All rooms have pillowy soft memory foam mattresses. You'll have access to the full home through a smartlock code.

Garden View Studio • Walk to Downtown • Fire Pit

✔ Prime Downtown Spot: In the heart of downtown Dundee, minutes from top attractions and dining. ✔ Outdoor Firepit: Unwind by the firepit, perfect for evening gatherings. ✔ Sleeps 4: Each unit accommodates up to 4 guests. 1 queen, 1 full sofa bed. ✔ Riverfront Location: Enjoy the scenic riverwalk just steps away. ✔ Off-Street Parking: Convenient and secure parking for your stay. ✔ Exclusive Group Booking: Reserve just one or all five units for your entire party.

Cozy French Inspired Cottage in rural setting

Relax and escape to our charming, one of a kind cottage. Beautifully decorated with period furniture and tastefully updated with modern amenities. The cottage offers slate tile and hardwood floors. Original pine floors line the upstairs loft bedrooms. Cook in a French inspired country kitchen with butcher block counter tops. Rural setting, yet minutes away from everything! Downtown is a 20 min. walk and the Metra will take you to the city in 45 minutes!

Designer's Dream in the North Shore!

Welcome to the newly designed cottage at Longmeadow. A tranquil escape from the city hustle of Downtown Chicago. Enjoy the serene setting while close proximity to town amenities, public transit and beautiful trails and parks. A cozy retreat in the wintertime to snuggle up with a great book and hot cocoa. It's also a perfect summer cottage for adventurers looking to take advantage of the beautiful landscape ! Check us out on: Instagram! longmeadowcottage

124 Lofts - Downtown Dundee - Walk to Dining

124 Lofts is a boutique collection of modern, design-forward lofts set within a beautifully restored historic building in downtown West Dundee. This listing is for Loft #1, a one-bedroom space featuring exposed brick, timber ceilings, and clean finishes that feel both character-driven and easy to enjoy. Each loft includes a king bed, private bath, kitchenette, fast Wi-Fi, and a 60" smart TV, just steps from restaurants, shops, and the Fox River.