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House vacation rentals in Highland Park

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Top-rated house rentals in Highland Park

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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.

Sep 27 – Oct 4

G$108,037 GYD per night

Home in Berwyn

4.92 out of 5 average rating, 238 reviews

Private apartment with retro vibe

Gunderson Getaway is a cosy one BR apartment with some retro style touches in Berwyn a block from Oak Park. 2nd floor private apartment. Wifi, cable, premium channels. Full kitchen. Queen bed plus sofa & extra single bed available. EASY free street parking right by unit. Quick drive to City. Convenient to both airports, United Center and walk to Fitzgerald’s Club. Near Blue Line, restaurants, groceries, great bakery. NO smoking, candles or glitter! Pets MUST be pre-approved and never left alone.

Sep 14 – 21

G$20,118 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.

Dec 15 – 22

G$27,102 GYD per night

Home in Highland Park

4.9 out of 5 average rating, 125 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!

Jan 23 – 30

G$238,399 GYD per night

Home in Twin Lakes

4.93 out of 5 average rating, 134 reviews

Cove at 420: Modern Lake Front Home near Chicago

Welcome to the Cove at 420. A modern vacation paradise where indoor and outdoor lines blur. Every space is designed for enjoyment. A short 75 minute drive from Chicago, this is a true retreat. Wake up to beautiful sunrise views or enjoy them from a kayak on the water. We offer kayaks, paddle boards, hot tub & sauna, Sonos sound system, a fire pit and plenty of yard games for our guests. Hidden on a cul-de-sac between Lake Mary and Lake Elizabeth, enjoy the best of lake life!

Sep 14 – 21

G$116,719 GYD per night

Home in Des Plaines

4.78 out of 5 average rating, 305 reviews

Urban Farmhouse near O'Hare

I am hosting a hundred year old farmhouse that has been completely renovated on the inside and outside. The beds are top quality and bought new. The neighborhood has unique places to dine and explore. It is close to Metra Rail Road to downtown Chicago. O'Hare International Airport is 7 miles from the house and Rosemont Convention Center is just 5 miles, both are accesable by car or public transportation. There is also a lot of parking. A great place to stay when you travel.

Nov 17 – 24

G$25,389 GYD per night

Home in Ingleside

4.93 out of 5 average rating, 110 reviews

Gorgeous Nautical 2/2 Lake House Chain O' Lakes

Unique and cute 2 bed / 2 bath nautical lake house has the best views of the Chain O' Lakes. Be amazed on the walk out lake view wood deck in the back yard, and watch sunsets fall over the bay and color the sky. The back patio is a great place to relax, entertain & relax. Fish or dock your watercraft at our pier if needed. There is an optional 5-6 person hot tub on the back deck for you to relax and unwind (See access and maintenance fee). Fully remodeled modern lake house

Nov 20 – 27

G$42,338 GYD per night

Home in Round Lake Beach

4.89 out of 5 average rating, 151 reviews

Corner Lakefront Property

This unique place has a style all its own. This corner lake house comes with a huge fenced-in yard, as well as a balcony off of the master bedroom and 2 parking spots. We offer 3 kayaks with life jackets, 1 paddle board, paddle boat and fishing poles, fire pit, outdoor and indoor games. We have 3 bedrooms with beds included, as well as a futon couch a trundle bed and a pull-out couch bed (6 potential beds total). This comes with 2 TVs, fireplace, WiFi, bar, new fridge and more.

Feb 26 – Mar 5

G$48,825 GYD per night

Home in Round Lake Beach

4.99 out of 5 average rating, 100 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!

Dec 8 – 13

G$38,619 GYD per night

Home in South Elgin

4.98 out of 5 average rating, 191 reviews

"Blackhawk on the Fox", Fire Pit and Tire Swing!

Greetings all! We call our place "Blackhawk on the Fox". It's a private riverfront two bedroom 750 sqft house with 1 bathroom on just under an acre property. A special place to relax, do some fishing, grilling, and roasting marshmallows on the fire. Located in a secluded unincorporated Fox River neighborhood in Kane County just a half mile from Blackhawk waterfall via bike path. The subdivision is hidden between the Jon J. Duerr and Blackhawk forest preserves.

Sep 3 – 10

G$43,799 GYD per night

Home in Elgin

4.88 out of 5 average rating, 103 reviews

Charming Elgin Home with a Great Location

Come enjoy this beautifully restored and charming historic home from the early 1920s. Our place is good for couples, families or for a getaway with friends. Outdoor space with fully fenced backyard. This 2 bed 1 bath has been fully restored and is absolutely adorable! Walking distance to downtown Elgin (less than one mile) and Metra station (only one hour train ride into the city!), and less than 5 minute drive to I-90. Relax and get cozy in this adorable space.

Oct 3 – 10

G$27,448 GYD per night

Home in Kenosha

4.97 out of 5 average rating, 197 reviews

Lovely home near the beach in a safe neighborhood

Our simple, yet welcoming property is minutes away from beaches, downtown, minor league baseball, the farmers market, and many delicious restaurants, as well as having close proximity to Carthage College, 6 Flags, and a quiet 30 min drive to Great Lakes Naval Base. We are located in the Allendale neighborhood boasting a family-friendly atmosphere on a quiet street. Whether you are here to relax, have fun, or attend special events, our house can provide.

Oct 17 – 24

G$26,300 GYD per night

Vacation rentals for every style

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Popular amenities for Highland Park house rentals

Free parking on premises

Air conditioning

House rentals with a pool

Home in Grayslake

4.95 out of 5 average rating, 109 reviews

Huge Indoor Pool &Theater - link moved see details

Aug 28 – Sep 4

G$148,324 GYD per night

Home in Lake Forest

4.91 out of 5 average rating, 58 reviews

Beautiful 137 Year Old Farm Home (3night min)

Mar 1 – 8

G$167,863 GYD per night

Home in McHenry

5.0 out of 5 average rating, 35 reviews

Highwood Haven

Oct 9 – 16

G$222,611 GYD per night

Home in Schaumburg

4.93 out of 5 average rating, 14 reviews

Schaumburg Woodfield Pool House 4bedroom 2.5bath

May 25 – Jun 1

G$126,388 GYD per night

Home in Grayslake

5.0 out of 5 average rating, 15 reviews

Family-sized Indoor Heated Pool & Movie Theater!

Mar 8 – 15

G$172,842 GYD per night

Home in Twin Lakes

5.0 out of 5 average rating, 27 reviews

#EnglishPrairieBnB "Lite" | An Experiential Stay!

May 10 – 17

G$194,554 GYD per night

Home in Genoa City

5.0 out of 5 average rating, 34 reviews

Family Getaway by Lake Geneva - Games Pool & Yard

Feb 11 – 18

G$69,346 GYD per night

Home in Glen Ellyn

4.94 out of 5 average rating, 16 reviews

Glen Ellyn Home

Jul 23 – 30

G$106,762 GYD per night

Weekly house rentals

Home in Montgomery

4.84 out of 5 average rating, 109 reviews

Nice, Private Ranch Home

Jul 22 – 29

G$31,454 GYD per night

Home in Fox Lake

4.9 out of 5 average rating, 128 reviews

Charming Lake Cottage ★ Queen Bed ★ Chain O Lakes

Mar 13 – 20

G$29,914 GYD per night

Home in Chicago

4.98 out of 5 average rating, 205 reviews

Wrigleyville Southport Studio

Nov 28 – Dec 5

G$33,141 GYD per night

Home in Highland Park

4.98 out of 5 average rating, 59 reviews

Charming Ranch-Style Cottage

Apr 2 – 9

G$35,134 GYD per night

Home in Highland Park

4.92 out of 5 average rating, 39 reviews

Witness Sunrise Over Lake Michigan

Oct 1 – 8

G$239,443 GYD per night

Home in Northbrook

5.0 out of 5 average rating, 16 reviews

Northbrook Retreat with Ample Outdoor Space

Sep 10 – 17

G$69,138 GYD per night

Home in Highland Park

4.86 out of 5 average rating, 43 reviews

A Wonderful Getaway Home on the North Shore!

Dec 9 – 16

G$44,204 GYD per night

Home in Deerfield

4.96 out of 5 average rating, 26 reviews

Lake Forest Country Estate

May 20 – 27

G$56,995 GYD per night

Private house rentals

Home in Waukegan

4.86 out of 5 average rating, 36 reviews

* Cozy Wauk-Townhse near navy base

Jan 1 – 8

G$25,604 GYD per night

Home in Palatine

4.85 out of 5 average rating, 39 reviews

Private Room with attach bath and personal kitchen

Sep 29 – Oct 6

G$14,087 GYD per night

Home in Waukegan

4.91 out of 5 average rating, 65 reviews

The Indigo Cottage

Oct 11 – 18

G$32,871 GYD per night

Home in Libertyville

5.0 out of 5 average rating, 11 reviews

Private Get A Way

Oct 5 – 12

G$95,090 GYD per night

Home in Antioch

4.96 out of 5 average rating, 27 reviews

Hideaway Lakehouse

May 2 – 9

G$29,573 GYD per night

Home in North Chicago

4.97 out of 5 average rating, 33 reviews

Spacious 2-br, 1 bath home w/AC near Naval Base

Jan 10 – 17

G$35,394 GYD per night

Home in Evanston

5.0 out of 5 average rating, 55 reviews

Larimer Park Carriage House

Mar 23 – 30

G$48,696 GYD per night

Home in North Chicago

4.95 out of 5 average rating, 56 reviews

The Perfect home for the family!

Jul 20 – 27

G$44,137 GYD per night

Quick stats about house rentals in Highland Park

Total rentals
30 properties
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
1.1K reviews
Nightly prices starting at
G$8,363 GYD before taxes and fees

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