Holiday rentals in Kenilworth

4.97 out of 5 average rating, 154 reviews

Home in Wilmette

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.

4.65 out of 5 average rating, 105 reviews

Flat in Wilmette

2 BR Apartment steps from downtown Wilmette

Recently updated with new furniture, light fixtures, and design touches! Ideally located near downtown Wilmette and the Metra. Wood burning stove in sitting room, fully outfitted kitchen with a dishwasher, full stove, microwave, full fridge, laundry in the basement (shared), off-street parking for one vehicle. Living room with sofa and a large flat-screen TV with Roku. The owner's office is on-site. Some pets OK with additional non-refundable fee per pet. We do not allow dogs over 35 lbs.

4.99 out of 5 average rating, 659 reviews

Guest suite in Geneva

A Suite within a Cozy cottage in Geneva Illinois.

Cozy private suite in the lower level. Guests have the suite to themselves. The bathroom is adjacent to the room and is private. There is a small fridge, a coffee maker, and a microwave oven. We are in Geneva, Illinois. We are LGBTQ+friendly. Our space is ideal for shorter stays and visitors on the go . Not suitable for staycations. Quiet area. Hosts live on the upper level and guests pass through our space to get to the suite. In a bind we can accommodate a 3rd guest and a pet. Welcome.

5 out of 5 average rating, 40 reviews

Guest house in Evanston

Mr. Hughes’ Attic, an 80s-themed hideaway

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.

4.97 out of 5 average rating, 500 reviews

Flat in Evanston

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.

4.98 out of 5 average rating, 256 reviews

Guest suite in Evanston

A guest suite centrally located, but so quiet

IF... you want to race into the city to see a play, go for a jog along the lake, have a quick coffee with a friend or enjoy a fine restaurant to celebrate a special occasion, it's all here in the lovely lakeside town of EVANSTON, IL. You can enjoy it all while living in my private guest suite w/kitchenette, private bath, private entry, shared laundry area and......., if you need it, garage parking, too! Enjoy my garden on warm summer days; in winter, you will love the heated floor!

4.87 out of 5 average rating, 151 reviews

Home in Evanston

SW Evanston Private, Stylish, Spacious Suite

Comfort and convenience abound in this stylish suburban suite! Mid-century and vintage motif meets modern touches and style. Guests have the entire basement, with a private bedroom, bathroom, huge living space, and a private entrance in a quiet house on a beautiful treelined street. Backyard access, coffee, easy street parking. Walking distance to parks and public transportation, a short drive to downtown Evanston and the lakefront, easy access to Chicago, Northwestern. Loyola, Skokie.

4.9 out of 5 average rating, 266 reviews

Flat in Wilmette

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.**

4.96 out of 5 average rating, 138 reviews

Flat in Evanston

Cozy Neighborhood Escape | Near NU-Chicago-Beaches

This is a beautiful, newly renovated apartment that is cozy and contemporary! This unit is located in Evanston’s arts district, surrounded by local shops, tree lined streets, and is a short distance to restaurants, the lakefront, and Northwestern University. Evanston is a suburb just north of Chicago with easy access to the city either by car or public transit. This apartment sleeps up to 4 people and is a 1 bedroom, 1 bath with a sofa sleeper. Don’t miss out. Book Now!

4.89 out of 5 average rating, 647 reviews

Flat in Skokie

Cozy Garden Unit in Quiet Neighborhood

A cozy garden unit in the heart of skokie, off of a quiet residential street with plenty of street parking. Just a mile away from the Skokie-Dempster Yellow line train that leads to downtown Chicago, and within a mile from Old Orchard Mall and plenty of great eateries such as: Chick-fil-A, Portillo's, Culver's, Oberwies, Kaufman's Bagel, and more. 15 minutes away from Evanston and the Beautiful Lake Michigan shoreline!

4.89 out of 5 average rating, 37 reviews

Flat in Wilmette

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.

4.77 out of 5 average rating, 641 reviews

Apartment in Evanston

Spacious Evanston Unit - Walk to Northwestern U

Welcome to my contemporary and spacious garden level unit located on a tree filled, serene residential block in Evanston. Walking distance to Northwestern University, retail areas, trains, golf, and the lovely beaches of Lake Michigan! A Walgreens and a local brewery restaurant are just a few steps away. Plentiful free street parking and free EV chargers one block away.

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Other great holiday rentals in Kenilworth

Private room in East Rogers Park

4.95 out of 5 average rating, 41 reviews

Private Room in Rogers Park

HenryRating, 5 stars6 days ago

Victor and Rudia are very communicative and provide clear instructions. The room is clean, and I had an enjoyable stay!

4.81 out of 5 average rating, 74 reviews

Private room in Evanston

1 Room for up to 3, Near NU & Old Orchard Mall

Elena ARating, 5 stars2 weeks ago

Nancy was a terrific host for my son and I. We enjoyed the house and a beautiful garden, and Nancy made every effort to make our stay comfortable and memorable.

4.99 out of 5 average rating, 197 reviews

Private room in Evanston

Comfortable Private Room in Owner Occupied Home

GentRating, 5 stars1 week ago

Great place to stay. Stephen was a great host. Friendly and welcoming.

4.75 out of 5 average rating, 65 reviews

Private room in Evanston

Beautiful Space in Evanston Chicago Bungalow

AnnaRating, 5 stars6 months ago

Lovely space for a small family. Nice to be by a park, quiet area and close to major streets as well. Peaceful and nice stay!

4.9 out of 5 average rating, 41 reviews

Private room in Skokie

Cozy Private Room

AliRating, 5 stars1 month ago

Peaceful place, great hosts!

4.91 out of 5 average rating, 11 reviews

Private room in Skokie

Home of Peace

RobertRating, 5 stars3 weeks ago

I greatly enjoyed the stay! T was a great host.

Private room in Norwood Park

4.95 out of 5 average rating, 64 reviews

+Safe Area-Laundry-42" TV-Mini Fridge + More!

JeffreyRating, 5 stars1 week ago

Needed safe, simple, non-fussy and affordable lodging for a longer solo vacation (11 days) in the city to do different activities around the city but also work remotely for several days. This place was a perfect fit in all ways! There were other guests staying at the property (plus the owner, Joey for a few days) and everything went smoothly, considerately, and stayed quiet, calm, comfy, and clean. Slept great thanks to mattress quality, window fan/AC unit, and ceiling fan. Remote Work went great thanks to big desk and mini fridge in room. Street parking was the easiest and safest of any of my trips to Chicago with a car for 15+ years.