Holiday houses in Northfield

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Top-rated holiday rentals in Northfield

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

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Guest favourite

A cozy living room features a pair of light-colored sofas and an accent chair, positioned around a rustic coffee table. A patterned area rug lies underfoot, while a mirror with a wooden frame and wall art enhance the space. A partial view of the kitchenette is visible in the background.

Home in Highland Park

4.94 out of 5 average rating, 179 reviews

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!

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Top Guest favourite

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.

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Top Guest favourite

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, 130 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.

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Top Guest favourite

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, 497 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.

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Guest favourite

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.

ValueFamilyIndoor spaces

Top Guest favourite

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, 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.

LocationFamilySleep quality

Guest favourite

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

4.92 out of 5 average rating, 63 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!

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Superhost

Guest suite in Highland Park

4.77 out of 5 average rating, 194 reviews

Your relaxing stay in Highland Park

Whether you are looking to escape the city hustle and bustle, visiting Lake Forest College, the Naval Station or moving cross country, our bright and spacious suite is the perfect spot to check in and relax for a few nights. Featuring a separate entrance and a beautiful, private newly remodeled bathroom. 43 4K Smart HDTV with Netflix and Prime and super fast WiFi available for streaming. Kitchenette with a microwave, mini fridge, sink and cups/plates/010/053/2026cutlery.

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Guest favourite

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

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Guest favourite

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

4.89 out of 5 average rating, 96 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.

LocationFamilyLong stay

Top Guest favourite

Home in Highland Park

4.95 out of 5 average rating, 20 reviews

5 min to Ravinia*Navy Base*Sleeps 7*Smart TVs

Spacious 3BR, 4BA home in Highland Park—steps from Ravinia Festival and the Botanic Garden, just 20 mins to the Navy base, and a quick train ride to downtown Chicago. Enjoy an open-concept living area, fully equipped kitchen, and comfy bedrooms—perfect for families, military guests, or concert fans. Unwind after a day exploring the area and discover all that Highland Park has to offer. Book your stay for comfort, convenience, and local charm!

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Guest favourite

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.

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