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Vacation rentals in Deerfield

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Top-rated vacation rentals in Deerfield

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Home in Highland Park

4.9 out of 5 average rating, 120 reviews

Rejuvenate and Relax in the North Shore

Set in the midst of an affluent neighborhood, this spacious and sunny four bedroom retreat offers all the comforts of a home away from home. With it's perfect location close to Lake Michigan, Chicago Botanical Garden, Ravinia, Naval Base, and Six Flags Great America to name a few, our family home is within reach to Chicago as well. If you feel very adventurous, just leave your car in garage, pick up a bike and ride the Lake Shore Bike trail all the way to downtown Chicago, enjoying the beautiful scenery. If you feel less adventures but still would like to enjoy beautiful scenery, you can do it by taking a train. Metra can get you downtown Chicago in less than 45 min. and the stop is within walking distance.

Home in Wilmette

4.98 out of 5 average rating, 128 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.

Guest suite in Wood Dale

4.9 out of 5 average rating, 462 reviews

The Deer Suite

This is a one bedroom apartment within the home. NOT FOR PARTY No Smoking , ABSOLUTELY No events, parties, or large gatherings. The apartment has a separate entrance from the home main entrance. The apartment also comes with comcast high speed internet. The living room couch can be turned into a double bed, that sleeps two. Large ,shower towels and shampoo included. The apartment includes washer and dryer.The bedroom sleeps two .It is about 30min drive to Downtown-Chicago and15min to O'hare .

Treehouse in Schaumburg

4.93 out of 5 average rating, 770 reviews

Enchanted Garden Treehouse (Amenity*)

Fall is here, the trees are beginning to turn, and the treehouse is warm and cozy! Relax on cool evenings in our luxurious, very private, new 4' deep cedar hot tub nestled in the evergreens, while the stars and moon swirl overhead, the waterfall tumbles into the koi pond, and the fire table and torches blaze. The running stream makes this a wildlife refuge, with tons of birds, squirrels, rabbits and even foxes and hawks. We are 420 friendly. Come experience the magic and make a special memory!

Rental unit in Highland Park

4.86 out of 5 average rating, 98 reviews

Chic Studio in Downtown Highland Park near Metra

Welcome to downtown Highland Park! Experience comfort and convenience in our cozy studio apartment with FREE parking. Just a 5-minute walk to the Metra, and within a leisurely 15-minute stroll, enjoy breathtaking views of Lake Michigan. Explore historic Fort Sheridan Forest Preserve and beach, only a quick 5-minute drive away. Discover delightful dining, gelato shops, parks, and more—all within walking distance. Our well-appointed apartment ensures a memorable stay in this vibrant neighborhood.

Home in Beach Park

4.97 out of 5 average rating, 192 reviews

B’s Farmhouse Cottage 2-bedroom duplex.

Experience the best of the midwest! Enjoy a newly remodeled "Magnolia Farm" inspired 2-bedroom duplex, all to yourself near everything you need. 50 Miles from Milwaukee, miles from Chicago, and 2 miles having your toes in the sand at Lake Michigan. We are minutes away from the Great Lakes Naval Station and the Cancer Treatment Center of America, Six Flags Great America, Gurnee Mills, and Great Wolf Lodge. Whatever brings you here make J&B's Farmhouse Cottage your home away from home today.

Rental unit in Highland Park

4.93 out of 5 average rating, 148 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 suite in Riverwoods

4.95 out of 5 average rating, 355 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.

Guesthouse in Lake Forest

4.95 out of 5 average rating, 115 reviews

The Green Door - safe and calm with walkability

This charming guesthouse in Lake Forest is only steps away from beautiful Market Square — the historic retail center of the community. Inside it features loads of light, in-unit washer and dryer, a well-equipped kitchen and a professionally designed stylish and calming interior. Outside, it has a vintage (ie. older) porch/breezeway with classic outdoor games. Walk to two grocery stores, bars/restaurants and our historic train station that connects to Chicago and various corporate shuttles.

Home in Highland Park

4.91 out of 5 average rating, 140 reviews

2-Acre Highland Park Retreat with Heated Pool ~ 5*

Experience luxury of this award winning 6BR 4Bath family home in picturesque Northshore private estate. Spend day by the private heated pool, enjoy beauty of gardens, explore local landmarks, starting with the gates of neighborhood Michael Jordan estate. The stylish design and rich amenity list will leave you in awe. ✔ Two-Acre Estate ✔ 6 Comfy BRs ✔ Multiple Living Areas ✔ Full Kitchen ✔ Backyard (Pool, Lounges, BBQ) ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Free Parking See more below!

Home in Round Lake Beach

4.99 out of 5 average rating, 121 reviews

Round Lake Getaway Retreat

Looking for a calming, peaceful lakeside getaway for you and your loved one? Come stay at our remodeled retreat with private waterfront access to Round Lake. Enjoy peace and reflection meditating on the spirited lake waters rolling into shore. Wake up to inspirational lake views with soul warming coffee, tea or cocoa. Savor deep or lazy conversation with your loved one, surrounded by dreamy décor and captivating nature. Come and relax, restore, and rejuvenate by the lake!

Home in Lake Bluff

4.93 out of 5 average rating, 119 reviews

Home Sweet Home, minutes to Great Lakes Naval Base

Home Sweet Home is located 35 miles north of Chicago; 53 miles south of Milwaukee, WI; and just 4 miles east of Great Lakes Naval Base. Chicago is a 45-minute train ride away. O'Hare is a 30 to 40-minute commute. Great America amusement park and shopping venues, including Gurnee and Kenosha outlet malls, are all within 20 to 30 minutes away. Location makes this home an ideal respite for Midwest sightseeing.

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Popular amenities for Deerfield vacation rentals

Free parking on premises

Air conditioning

Stay near Deerfield's top sights

Northbrook Court11 locals recommend

Jewel-Osco9 locals recommend

Whole Foods Market5 locals recommend

AMC DINE-IN Northbrook Court 145 locals recommend

Walgreens3 locals recommend

The Italian Kitchen3 locals recommend

Other great vacation rentals in Deerfield

Guesthouse in Arlington Heights

4.95 out of 5 average rating, 41 reviews

Cozy Chicago Suburban Apartment

Home in Lake Bluff

4.92 out of 5 average rating, 26 reviews

3 bedroom, living & family room, screened porch

Home in Arlington Heights

4.94 out of 5 average rating, 66 reviews

Casa Blanca, 5 Beds

Home in Libertyville

5 out of 5 average rating, 23 reviews

Private Get A Way

Home in Glenview

5 out of 5 average rating, 17 reviews

Cozy Home Inn Glenview

Home in Highland Park

5 out of 5 average rating, 28 reviews

Sanctuary on the Ravine

Home in Palatine

4.85 out of 5 average rating, 46 reviews

Private Room w/ attached bath and personal kitchen

Home in Arlington Heights

4.97 out of 5 average rating, 38 reviews

The PristineRetreat. Families, kids, pets welcomed

Quick stats about vacation rentals in Deerfield

Total rentals
10 properties
Nightly prices starting at
$50 before taxes and fees
Total number of reviews
360 reviews
Wifi availability
10 properties include access to wifi
Popular amenities
Gym, BBQ grill, and Laptop-friendly workspace
Local attractions
Jewel-Osco, Whole Foods Market, and Jimmy Thai/Ramen Time

Destinations to explore