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Vacation rentals in Deerfield

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Top-rated vacation rentals in Deerfield

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

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Home in Highland Park

4.91 out of 5 average rating, 109 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.

Dec 11 – 18

G$101,664 GYD per night

Apartment in Park Ridge

4.79 out of 5 average rating, 319 reviews

Modern Garden apartment (WHOLE UNIT)

Freshly Remodeled , Lower Level Condo one bedroom one bath. The Condo is very large for a one bedroom. Very Spacious with its open concept layout. Parking is right next to the main entrance of the building. Perfect place to relax Perfect and safe place to rest . 24/7 perimeter monitoring cameras. The Condo is very close to the Metra Train. It is !5 min away from O'Hare airport and 10 min from Chicago outlets etc. It is not a party room . No parties or large gathering .... Garden Apartment

Nov 21 – 28

G$30,393 GYD per night

Home in Northbrook

5.0 out of 5 average rating, 14 reviews

Northbrook Retreat with Ample Outdoor Space

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.

Jun 27 – Jul 4

G$75,450 GYD per night

Home in Highland Park

4.98 out of 5 average rating, 58 reviews

Charming Ranch-Style Cottage

Escape the hustle and bustle of the city in this relaxing, cozy, cottage that is a few blocks away from downtown Highland Park and Highwood, with great restaurants, bars and coffee shops. It is perfect for single travelers, couples, or a small family. We are grateful for the amazing Airbnb hosts across the globe, who opened their homes to us, and made our trips so memorable. So when we bought our own home, it was only right that we would return the favor and open our home to fellow adventurers

Nov 4 – 11

G$34,291 GYD per night

Home in Beach Park

4.98 out of 5 average rating, 161 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.

Jun 9 – 16

G$28,785 GYD per night

Apartment in Arlington Heights

4.99 out of 5 average rating, 112 reviews

Ideal Location in Awesome Heights

Near the heart of downtown Arlington Heights and convenient to O’Hare. You can settle in at this cozy basement apartment with a super comfortable queen bed and all the amenities you’d need. Whether your visit to AH is for business or pleasure, city or suburbs, we look forward to hosting you. The private apartment works great for guests with a car or using public transit. Easy access to Metra station, AH restaurants, Des Plaines Theater, NW Community Hospital & Schaumburg Convention Center.

Jun 11 – 18

G$29,798 GYD per night

Apartment in Highland Park

4.94 out of 5 average rating, 122 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.

Feb 15 – 22

G$40,464 GYD per night

Guest suite in Riverwoods

4.95 out of 5 average rating, 300 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.

May 26 – Jun 2

G$34,747 GYD per night

Guesthouse in Lake Forest

4.95 out of 5 average rating, 95 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.

Feb 4 – 11

G$20,525 GYD per night

Apartment in Highland Park

5.0 out of 5 average rating, 38 reviews

Stunning & Stylish Downtown Studio - Highland Park

Experience the charm of downtown Highland Park, IL, in our newly-remodeled, stylish studio apartment, steps away from the metra train! Our space boasts a modern design, two large skylights that flood the area with natural light, and a comfort you'll remember. Discover local shops, eateries, and galleries at your doorstep, the many shorelines and beaches , and retreat to a space that feels like home yet whispers luxury and comfort. Your Highland Park adventure starts here.

May 8 – 15

G$20,865 GYD per night

Guest suite in Zion

4.9 out of 5 average rating, 136 reviews

Non-smoking, attached mother-in-law suite.

30 minutes away from the Naval Station 5 minutes away from the beach. 10 minutes to Wisconsin. 1 hour to O’Hare Airport and downtown Chicago. 1 hour to Milwaukee 25 minutes to Six Flags and Great Wolf Lodge. Safe and quiet neighborhood with plenty of wildlife right in the back yard. This Mother in Law suite has tons of natural light. For nature lover’s this unit is close to the beach and there are walking trails nearby. Small children maybe heard from 7AM to 7PM.

May 5 – 12

G$16,799 GYD per night

Townhouse in Hoffman Estates

4.91 out of 5 average rating, 291 reviews

a SIMPLE place

Booking the entire house with 100% privacy. It has 2 driveway parking spaces and street parking. Garage may be available. CHECK-IN and OUT are flexible. I set checkout at 11am (text me if you need late checkout). The space is perfect for a family of 4. It is located about 20 minutes from O'Hare airport and 40 minutes from Chicago downtown. Infants and pets are welcome (please text me for over size pets or more than 2 pets) Play pan is available upon request.

Dec 19 – 26

G$20,303 GYD per night

Vacation rentals for every style

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Popular amenities for Deerfield vacation rentals

Free parking on premises

Air conditioning

Stay near Deerfield's top sights

Whole Foods Market5 locals recommend

Jewel-Osco9 locals recommend

The Italian Kitchen3 locals recommend

Other great vacation rentals in Deerfield

Apartment in Highland Park

5.0 out of 5 average rating, 12 reviews

Full Apartment green oasis in law suite

Apr 27 – May 4

G$37,545 GYD per night

Cottage in Libertyville

5.0 out of 5 average rating, 23 reviews

Woodland Guest House-Vintage Libertyville Chicago

Oct 4 – 11

G$16,810 GYD per night

Guest suite in Northbrook

4.9 out of 5 average rating, 73 reviews

ELEGANT 2BR/2BA NORTHSHORE GARDEN APARTMENT

May 20 – 27

G$48,093 GYD per night

Guest suite in Lake Zurich

5.0 out of 5 average rating, 13 reviews

Private Entrance, Two Bedroom *Pet Friendly*

Sep 14 – 21

G$21,310 GYD per night

Cottage in Highland Park

4.96 out of 5 average rating, 47 reviews

Re-imagined 1880s cottage by Highwood, Metra, Lake

Sep 15 – 22

G$58,753 GYD per night

Home in Lake Forest

5.0 out of 5 average rating, 5 reviews

Parkside Cottage Near the Train

Dec 9 – 16

G$32,813 GYD per night

Apartment in Libertyville

4.91 out of 5 average rating, 85 reviews

131 East Park Ave. #308

Sep 25 – Oct 2

G$19,123 GYD per night

Guesthouse in Lake Forest

4.88 out of 5 average rating, 80 reviews

Adorable Carriage House East Lake Forest

Jan 11 – 18

G$46,497 GYD per night

Destinations to explore