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
Apartment in Evanston
4.97 out of 5 average rating, 36 reviews

Private entrance to bed, bath, lounge and kitchen

Private entrance to downstairs 1 bedroom suite in our home. Sitting room with 44” TV, bath with shower, fully equipped kitchen. New queen mattress with premium linens. Small dedicated outdoor sitting area. Residential neighborhood 1/2 mile from beaches, parks and bike paths. Two miles to downtown Evanston's restaurants, shops and Northwestern University. Near public trans.Thirty minutes north of downtown Chicago; 1/2 hr south of renowned Ravinia Park and Botanic Garden. Free street parking.

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, 210 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
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, 496 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.

Superhost
A well-appointed living room displays a comfortable sectional sofa and a leather ottoman at the center. Natural light filters through a large window, illuminating the wooden floor. A staircase ascends to one side, while decorative details enhance the inviting atmosphere.
Home in Evanston
4.84 out of 5 average rating, 38 reviews

Cozy Evanston Villa with cinema and massage sofa

Come and enjoy the beautifully decorated cozy home, perfect for family union and friends gathering. The theme of our cottage is to offer you a cozy and relaxing experience. House features Breville Espresso Latte maker, specially designed home Cinema and leather Massage chairs, a dedicated peaceful workspace with enjoyable view to the neighborhood. The central location of the house, close to the Lakeshore Beach and to Northwestern University campus gives a unique vibrant touch to this place.

Guest favorite
The historic manor house features a rich red brick facade adorned with lush green ivy. The spacious porch extends from the building, complemented by well-maintained gardens that enhance the inviting exterior. Large windows provide ample natural light, creating an open and airy ambiance.
Guesthouse in Evanston
4.94 out of 5 average rating, 140 reviews

Historic Coach House in Evanston Near Beach & Town

Stay in the Coach House of this exquisitely restored Historic Landmark Manor House, one block to Lake Michigan's beaches and close to town and NU. Enjoy the entire coach house which is renovated and includes a large bedroom with king bed and desk, a sun-filled living room/dining room, a full bath with claw-foot soaking tub and shower and a kitchen with amenities. The space can be equipped with an air mattress for an extra guest. Also available is a 3rd floor guest suite in the main house.

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 out of 5 average rating, 101 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.

Superhost
A cozy sitting area features a compact brown couch adorned with patterned cushions. Two large leafy plants are placed on either side, enhancing the calm ambiance. The floor is covered with green area rugs, creating a fresh and natural feel within a well-lit space.
Place to stay in Wilmette
4.64 out of 5 average rating, 22 reviews

Eco-friendly coach house near Chicago

This place is a calm and compact 2-level coach house, a wonderful place to relax and work. It is completely renovated, new and fresh! A living space with a bathroom on the first floor and a bedroom with a working station on the second floor. WiFi, portable A/C, kitchenette, a private exit to a backyard, and a parking spot. Central Wilmette, a Metro station 4 minutes walking distance. Close to Northwestern University. Parks, shopping, restaurants, and the library are a 2–10-minute walk.

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, 302 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.**

Guest favorite
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
4.81 out of 5 average rating, 125 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

Top guest favorite
A spacious outdoor seating area features a sectional sofa with navy blue cushions, arranged around a matching ottoman. The deck overlooks a serene landscape with greenery and flowerbeds, creating an inviting space for relaxation.
Apartment in Evanston
4.91 out of 5 average rating, 43 reviews

Garden Apartment Retreat /Walk to Northwestern

Charming garden apartment in Evanston, perfect for your visit to Northwestern or a Lake Michigan getaway. This private 1-bedroom retreat comfortably sleeps 4 and features a full kitchenette, free parking, and a shared backyard with a firepit. Enjoy a peaceful setting with easy walking access to the university, Ryan Field, local cafes, and public transit to Chicago. Your ideal home base for exploring Evanston!

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
4.93 out of 5 average rating, 61 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.

Top 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, 138 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