Vacation rentals in Riverwoods

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Top-rated vacation rentals in Riverwoods

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Top guest favorite
The cottage showcases a charming front porch adorned with white railings and lush green planters. Colorful flowers bloom in the garden, adding vibrancy to the landscape. The peaked roof and decorative gables enhance the inviting exterior, framed by trees providing a serene atmosphere.
Cottage in Highland Park
4.98 out of 5 average rating, 93 reviews

Re-imagined 1880s cottage by Highwood, Metra, Lake

Step inside Step back in time Cozy, 1880 built, re-imagined, ravine edged garden cottage Your home away from home. Escape the city and relax in our newly renovated historic cottage and gardens. Peaceful yet centrally located, vintage yet modern, Mere Cottage has so much to offer. Inside: You'll enjoy updated amenities in harmony with a distinctive vintage charm. The common area has an open layout, perfect for socializing. The kitchen and pantry (my favorite room!) are new from top to bottom and are fully stocked with any cooking gadgets you may need. Two bedrooms are joined by a Jack & Jill bathroom. The living room has a sofa that pulls out into full size bed. Outside: Jordan and I had fun redesigning the grounds from front to back. Enjoy the front garden from the rocking chair on our wrap around porch. Out back we've added a vegetable and perennial garden for you to take in. Dinner out on the back deck overlooking the garden is highly recommended! Guests have access to the entire home and grounds. Jordan and I live in the neighborhood and will be available if you need us! Our cottage is located in Highland Park, about 25 miles north of Chicago on Lake Michigan. We like to think we have the best of both worlds- being in a quiet residential neighborhood with walking access to numerous amenities right around the corner. We're a quick 5 minute walk to Highwood (the north shore’s restaurant district) and an 8 minute walk to the Metra train that can take you from Chicago to Kenosha and any place in between. We're also right on the North Shore bike path (bring your bikes!). Fort Sheridan is also close by and worth exploring for its interesting history, architecture, and nature trails. On foot: Many errands can be done on foot. We have some of the best restaurants and watering holes north of Chicago within walking distance. There is also a Walgreens convenience store 2 blocks away. By car: Getting around by car is also easy. Parking is readily available almost anywhere you'll visit. You can get to downtown Chicago in 30 minutes in ideal traffic. Train: The Metra (our train system) can also conveniently get you to and from various attractions including downtown Chicago (a scenic 45 minute ride), Ravinia music venue, the Chicago Botanic Gardens, Great Lakes Naval Base and many more. Bike: Pack your bikes! We're located on the north shore bike trail. Head north on the trail to check out the beautiful Fort Sheridan, Lake Forest, and quaint Lake Bluff. Head south to Ravinia, Chicago Botanic Garden, and numerous other beautiful villages along Lake Michigan. I bike often and will gladly point you to some great hidden gems! If you're flying into O'hare, we recommend taking an Uber to our cottage. We're about a 30 minute drive from the airport. Six Flags Great America is also a 25 minute drive away. Keep in mind that the bathroom is a Jack & Jill and is accessed from either bedroom. There is no access from the common area, so it could pose an issue at night when sleeping our max number of 6. Please keep things tidy and wash any dishes used during your stay. Out of respect for our neighbors (this home is located in a quiet residential neighborhood), no parties or large gatherings are allowed. No pets allowed.

Top guest favorite
A modern kitchen and living area are showcased within an open-concept space. The kitchen features stainless steel appliances and a large island with seating for three. The cozy living area includes comfortable seating and a low wooden coffee table, complemented by warm wooden flooring.
Apartment in Chicago
5 out of 5 average rating, 62 reviews

Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom

Why stay anywhere when you can experience luxury during your travels. This brand new 1-BR apartment was designed with a touch of elegance and offers amenities to make your experience not just satisfying, but memorable. At your finger tips is a full kitchen; luxury bathroom with enormous walk-in shower; separate bedroom w/ queen bed (extra day bed in living room to sleep 3 total); garage parking; garden access; cozy workspace; 2-Smart TVs; bicycle; ample storage for longer stays; WIFI; and more.

Top guest favorite
A bright living room features a mix of comfortable seating with a tan leather sofa and two light-colored armchairs. A wooden coffee table sits center stage, complemented by decorative items. Large windows allow natural light to flow in, enhancing the cozy atmosphere.
Home in Northbrook
4.98 out of 5 average rating, 87 reviews

*King bed *Outdoor Living *Sought-After Area

Welcome to our sophisticated ranch style home, nestled in the serene, central Chicago neighborhood of Northbrook. This carefully curated home offers a peaceful retreat in a walkable neighborhood with nearby shopping and dining. With its elegant decor, comfortable furnishings, and modern amenities, the home provides a haven of relaxation. Whether you're enjoying a cup of coffee on the private patio or exploring the area, this home provides the perfect backdrop for a memorable vacation experience.

Guest favorite
A welcoming living area features a comfortable leather sectional sofa positioned around a central coffee table. A brick fireplace adds warmth to the space, which is complemented by built-in shelves showcasing decorative items. Light grey walls contrast with dark curtains framing the window.
Home in Northbrook
4.85 out of 5 average rating, 20 reviews

6 Kings | Ping-Pong | Gazebo!

Discover a spacious retreat perfect for groups, featuring 6 king beds, multiple smart TVs (w/ complimentary Disney+ & Hulu), a ping pong table, & plenty of driveway parking! Enjoy meals at the dining or kitchen table, then relax in the large yard under the gazebo. With 3.5 baths, everyone has room to refresh. Its prime location offers quick access to the North Shore’s beaches or Chicago’s vibrant scene—perfect for families, work groups, or friends seeking comfort, entertainment, and convenience!

Guest favorite
A charming entryway is featured, showcasing a white shingled exterior with green shutters. Two metal chairs surround a small round table, providing a cozy outdoor seating area. The front door is framed by a gabled roof, inviting guests into the studio.
Apartment in Highland Park
4.91 out of 5 average rating, 183 reviews

Lovely studio near the beach! (and heated floors!)

Get away from the city to this studio in Highland Park. The newly renovated space has everything you need for a relaxing getaway—huge comfy couch, brand new bed with Brooklinen + Parachute bedding, pristine bathroom, and lots of amenities. Downtown Highland Park, Highwood, + the beach are just a walk away. There's access to grocery stores, restaurants, and shops, and you can retreat to the quiet of your studio when you're ready to unwind. Ps. For the winter months: We've got heated floors.

Guest favorite
A bright living space features a spacious sectional sofa accented with blue and white cushions. A round coffee table sits atop a decorative rug. A large clock adorns the wall, while a dining area with a wooden table and chairs is visible in the background.
Guest suite in Arlington Heights
4.93 out of 5 average rating, 55 reviews

Cozy Chicago Suburban Apartment

Welcome to our cozy apartment, perfect for solo travelers or couples looking for a comfortable stay in the quiet Northwestern suburbs of Chicago. Located in a quiet and serene neighborhood, this apartment offers easy access to all the best restaurants, cafes, and shops. Just 23 mins away from O’hare International Airport, 15 mins to Schaumburg Convention center & Woodfield Mall, and about 40 mins from the Chicago Downtown. Lake Arlington is a 10 mins walk away for Kayak and park activities.

Guest favorite
A well-defined stone pathway leads to the entrance of the prairie-style home, bordered by lush green grass and neatly trimmed hedges. Hanging flower baskets add vibrant touches above the cozy seating area, surrounded by the serene backdrop of towering oak trees.
Guest suite in Riverwoods
4.95 out of 5 average rating, 430 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.

Guest favorite
A comfortable living area is designed with a gray sofa and a black coffee table, complemented by a dining table. A work desk is positioned near large windows, allowing natural light. A ceiling fan is visible, and a flat-screen TV is mounted on the wall.
Apartment in Libertyville
5 out of 5 average rating, 23 reviews

305

Kick back and relax in this calm, stylish space. This peaceful, quiet apartment is walking distance to beautiful downtown Libertyville. The building is very nicely maintained with an elevator. Located 7 miles from Great Lakes Naval Base and 35 miles from downtown Chicago. The unit is very clean with all brand new furnishings and appliances including HD tv's in both the living room and bedroom. Free ample parking. On-site laundry one floor down. Fast wifi with a dedicated work space.

Superhost
Home in Lake Forest
5 out of 5 average rating, 6 reviews

Spacious Home-Great Lakes Close-Quiet Location

Executive Housing and Temp Relocation requests welcome — Top Ranked Lake Forest School District Kick back and relax at this charming 5BR, 4BA Lake Forest home—just a mile to the beach Tucked on a quiet street with a backyard that feels like your own private park, it’s perfect for family fun or a peaceful escape. Cook up something tasty in the full kitchen, play in the yard, or stroll to nearby shops and trails. Just an hour from downtown Chicago but feels like a world away.

Superhost
A cozy bedroom features a black metal bed frame adorned with soft pillows in pink and green hues. Textured white bedding is spread across the bed. Natural light filters through the large windows, complemented by light-colored curtains, and a nightstand sits beside the bed.
Guesthouse in Lake Forest
4.8 out of 5 average rating, 116 reviews

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

Guest favorite
A cozy living area features a yellow sectional sofa and a glass coffee table, surrounded by warm wood flooring. A TV is positioned on a white media console, while a bright bouquet of flowers adds a touch of color. A work desk can be seen in the background.
Apartment in Highland Park
5 out of 5 average rating, 11 reviews

Month-to-Month Secure 1 bedroom+office and dining

Our 1 bedroom + den apartment is peaceful & stylish for your monthly living needs. Very quiet building, 2nd floor apartment with no neighbors above or below. Centrally-located 2 blocks from UP-N Metra, the apartment includes: stocked kitchen (no dishwasher), free shared laundry, free overnight parking (must provide license plate), and private sleeping on a king-bed with adjustable base. An additional twin bed may be added for guests (added fee).

Guest favorite
A charming brick home is set amidst a lush green lawn, framed by trees and bushes. The two-story structure features a distinctive sloped roof and a welcoming front porch. Natural light enhances the inviting exterior on a clear blue sky day.
Home in Highland Park
4.9 out of 5 average rating, 79 reviews

A Wonderful Getaway Home on the North Shore!

A perfect place to visit the northern highlights of Chicago! 1/4 mile from Ravinia! 1.5 miles from the Botanic Gardens! 30 minutes from Chicago (an hour and a half from Milwaukee). Close to trains, planes, and easy automobile access. A two-bedroom gem in the heart of so many wonderful things. Other local places include Northwestern University, Lake Forest, Winnetka, and Lake County. I have a cat living here, but he will accompany me when I leave.

Popular amenities for Riverwoods vacation rentals

  1. Airbnb
  2. United States
  3. Illinois
  4. Lake County
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