Vacation rentals in Kenilworth

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Top-rated vacation rentals in Kenilworth

Guests agree: these stays are highly rated for location, cleanliness, and more.

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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 West Rogers Park
4.99 out of 5 average rating, 113 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
The living area features a cozy sofa and a patterned armchair, complemented by a glass coffee table. A television is positioned in one corner. Large windows invite natural light, while floor-to-ceiling curtains offer privacy. A potted plant adds a touch of greenery.
Home in Wilmette
4.98 out of 5 average rating, 217 reviews

Unique porcelain-enamel paneled "Lustron" home

This rare modern post war home has a style all its own. Created by Carl Strandlund in Columbus Ohio, it consisted of prefabricated porcelain enamel covered panels inside and out making it durable and easy to clean. Easing the postwar housing shortage and its maintenance free design were its selling points. Great care has been taken to reflect its true character so enjoy the well thought out floor plan and huge yard. Close to Northwestern, Gilson park beach, and downtown Chicago via car or train.

Top guest favorite
The living area features a spacious sectional sofa and a coffee table at its center. A TV is positioned against a light-colored wall, while a dining space can be seen in the background with a small table and chairs. Natural light is welcomed through multiple windows.
Apartment in Evanston
4.96 out of 5 average rating, 319 reviews

Stylish & Comfy Gem near Downtown~Balcony~Parking

My 2nd floor, 2 BD/1BA home sits in a quiet cul-de-sac, about 1 mi from downtown Evanston. A 15-min walk to the Dempster Purple line station, which brings you right into Chicago. Northwestern and Loyola are nearby for a visit too! The area has wonderful lakeside parks and beaches, so no matter the time of year, you'll appreciate the natural beauty! Grocery stores, coffee shops, and restaurants are within walking distance as well. -Electric Fireplace -Fully Equipped Kitchen -Queen Sized Bedrooms

Guest favorite
Home in Glencoe
4.93 out of 5 average rating, 15 reviews

3 Luxury Master Suites by Gardens, Lake & Chicago

Welcome to your elegant Glencoe retreat on Chicago’s North Shore. This bright & beautifully finished home offers the perfect mix of comfort and sophistication with its 3-bedroom, 3-bathroom + queen sleeper sofa & 2 living rooms. Each bedroom has its own full bathroom, giving every guest privacy and convenience — a rare luxury in a vacation rental. Minutes from Chicago Botanic Gardens & Glencoe Beach. Perfect getaway to spend sunny days enjoying the charm of the North Shore. Family amenities

Top guest favorite
A modern kitchen and dining area are presented, featuring a sleek island with bar stools and a dining table with six chairs. Natural light is provided by large windows, and contemporary fixtures enhance the space's functionality and design.
Apartment in Evanston
4.92 out of 5 average rating, 210 reviews

New 3bd/1.5 bth Apt w/private prkg

A perfect hideaway! This quiet, secluded unit is nestled in lush greenery within walkng dist (1.5M) to NWU. Enjoy our renowned restaurants and theaters, plus easy access to downtown Chgo’s many attractions via the Metra; Sleeps up to 7 guests, with 2 queen beds, 2 single beds, and an 8-foot couch in Liv rm; Ultra-modern kitchen equipped with everything; Dedicated parking space in rear of the bldng; free high-speed Wi-Fi is included. Host lives nearby and responds promptly to any inquiries

Top guest favorite
The exterior view of the property is framed by lush greenery, including small trees and ornamental plants. A stone pathway leads to the entrance, which features a light-colored door. The building's soft hues complement the natural surroundings under a clear blue sky.
Guesthouse in Evanston
5.0 out of 5 average rating, 104 reviews

Mr. Hughes’ Attic, an 80s-themed coach house

Welcome to Mr. Hughes' Attic, a private coach house that pays homage to John Hughes (who filmed many of his movies nearby!) Located in NW Evanston, your stay includes a queen bed, full kitchen, laundry, full bath, dedicated workspace, private balcony, free parking, streaming TV, and more. We're a short walk to Central St shops, restaurants and the Metra train, a five-minute drive to Northwestern, and less than 30 minutes to Chicago. Not wheelchair or ADA accessible. License# STR004.

Guest favorite
The living area features two comfortable gray sofas facing a low coffee table, with a wall-mounted TV displaying a nature scene. Large windows allow natural light to fill the space, and a potted plant adds a touch of greenery. Soft area rug enhances the inviting atmosphere.
Home in Wilmette
4.93 out of 5 average rating, 67 reviews

Luxury Home- NorthShore/Wilmette

Welcome to our luxurious, newly renovated home in beautiful NorthShore Suburb of Chicago. Perfect for families and business travelers. Parking on-site. Enjoy spacious bedrooms w/ attached baths, fully equipped kitchen, fast Wi-Fi, smart TVs, and entertaining basement with ping pong, pool table, and games. Located 1 minute from the highway, 20 minutes from downtown Chicago, close to Six Flags, golf courses, shopping centers, and beautiful Lake Michigan. Pets allowed. Book your stay today!

Top guest favorite
A light-filled living room features a comfortable beige sofa with an accent pillow and a light throw. Adjacent windows allow natural light to stream in, highlighting the wooden flooring and decorative area rug. A small side table holds a lamp, contributing to the calm atmosphere.
Apartment in Evanston
4.97 out of 5 average rating, 549 reviews

Charming, Sunny Apartment with Backyard Garden

House of the Blue Doors Enjoy staying with us in this spacious 1st floor flat. Furnished by the resident designer in tasteful neutrals, original curated artwork, one of a kind furniture and accent pieces. Sip morning coffee or a glass of wine in the sunlit kitchen or front porch, fire up the backyard grill for a barbecue. Soak in the award winning Chicago ceramic artist designed and made floor in the bathroom. Close to Northwestern, Chicago, Lake Michigan, everything Evanston offers.

Guest favorite
A modern living area is presented, featuring a comfortable sectional sofa adorned with yellow accent pillows. A large flat-screen Smart TV is mounted on the wall, providing entertainment options. Natural light filters through the window, highlighting the warm wood flooring.
Apartment in Evanston
4.92 out of 5 average rating, 183 reviews

NEW Fam-Frndly 3 bd 1 bth w/ EZ Parking near NU

Relax with the whole family or explore the city at this peaceful newly renovated 3bd/1bth apartment with plenty of free parking and in-unit washer/dryer. You’ll be close to everything when you stay at this centrally-located place. Only 2 mins from DT Evanston and 25 mins from DT Chicago! Just mins away from Northwestern and Loyola Universities. Enjoy the 65in and 55in Smart TVs, listen to your favorite tunes w/ the voice enabled Amazon Echo Alexa speaker, or enjoy family games.

Top guest favorite
The historic home exterior is showcased, featuring a vibrant red facade with white accents. A charming porch adorned with lattice and railings provides an inviting entrance. Lush greenery surrounds the property, complemented by a white picket fence and vibrant landscaping.
Apartment in Wilmette
4.9 out of 5 average rating, 305 reviews

Spacious Garden Apartment with Sauna and Fireplace

English garden apartment in historic Wilmette home with a private entrance, sauna, washer/dryer, kitchenette, dining area, recreation room with pool table, vintage pinball machine, and a wood-burning fireplace with gas igniter. Two queen beds, 1 full-size sleeper sofa, and a single mattress are available for large families. Ideal access to Northwestern University for all events. **Please note the apartment is located on the garden level and does NOT include the entire home.**

Top guest favorite
A green door with two circular brass handles and a sign reading 'THE SHOP' is set against a vibrant blue brick wall. The wall showcases its texture with a smooth finish. An electrical outlet is visible to the left of the door.
Apartment in Wilmette
4.94 out of 5 average rating, 65 reviews

The Shop - Trendy Studio in the heart of Wilmette

Located in the heart of downtown Wilmette, our studio offers a unique stay in a fantastic location. Recently updated with new furniture, kitchen finishes, and design touches! Spacious and within walking distance to all that Wilmette has to offer. This private apartment comes with an outfitted kitchen, cozy lounge area, full stove/oven, microwave, fridge/freezer, and one uncovered surface parking spot.

Guest favorite
An open-concept living area features large windows that invite natural light and provide a view of the cityscape. A comfortable blue sofa is adorned with patterned pillows, while a light wood coffee table sits in front of it. A dining space with black chairs complements the modern kitchen.
Condo in Evanston
4.96 out of 5 average rating, 140 reviews

"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux

Urban-Luxe experience at the Bliss of Evanston Condo. Elegant finishes and a sweeping Sky Terrace view of downtown Evanston. Resort-like amenities with fitness center, outdoor pool, free parking in indoor GAR, biz ctr, and much more. 2 bedrooms, 2 full baths, 2 roll-out beds welcome you to a comfortable stay near Northwestern University, Loyola, and Kellogg and minutes from Chicago Downtown.

Popular amenities for Kenilworth vacation rentals