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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

4.9 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.

Home in Berwyn

4.99 out of 5 average rating, 114 reviews

Retro Modern Bungalow— fire pit + free parking

Experience the city in style at Retro Modern Bungalow. The perfect crash pad for up to four friends and two pups. Featuring two spacious bedrooms, each w/ a king bed + luxury linens, a propane fire pit and a fully fenced backyard. Enjoy central HVAC, hi-speed WiFi, and a dedicated workspace. A pack-n-play crib is available at no cost. Central location just south of Oak Park, 15 mins from Midway airport, and 20 mins from downtown. Park for free in our garage or catch the train a few blocks away.

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.

Home in Fox Lake

4.9 out of 5 average rating, 142 reviews

Charming Lake Cottage ★ Queen Bed ★ Chain O Lakes

Outdoor enthusiasts will be delighted with this romantic 1 bedroom lake cottage that sleeps 4. The fall colors, hiking, and nature setting is especially breathtaking this time of year. Walk down to the lake to enjoy boating, swimming, fishing, and more. Experience all the comforts of home in this newly remodeled cottage desirably located on Lippincott Point. Perfect for romantic getaways, gathering with friends by the lakeside fire pit, boating “the chain” and all that lake life has to offer!

Home in Kenosha

5 out of 5 average rating, 125 reviews

LITTLE HOUSE by the BIG LAKE

Only steps away from Lake Michigan, our well-appointed home is your southeast Wisconsin retreat. The home is in a peaceful, safe neighborhood, less than 2 blocks from the Eichelman scenic park/beach. Kenosha's downtown which is loaded with fun shops, restaurants, cafes and breweries is a short walk away. Take a stroll to the harbor, lighthouse, Civil War Museum, and marina. Great Lakes Naval Station is 1/2 hour down the lakefront. Dates not available? Check out The Cozy Cottage next door.

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 Richmond

4.96 out of 5 average rating, 138 reviews

TheGlassCabin@HackmatackRetreat

The Pond House, a vintage glass cabin filled with art, water views & eclectic vibes privately perched on the sacred grounds of Hackmatack Retreat Center. Native prairie, a winding slow river, two ponds, 200+ year old oaks & big sky- Countless places to curl up, gathering, focus-- nooks and crannies indoors and out, we offer “time out for time in” amidst this noisy world. Minutes from 2 small towns, all amenities, we're all about peace & ease-- let us custom curate your experience !

Home in Lake Geneva

4.88 out of 5 average rating, 210 reviews

Beautiful Home w/ Hot Tub in Lake Como, Wisconsin

Enjoy time with friends and family in this fully equipped 2 bedroom 1 bathroom home in the great neighborhood of Lake Como. Our house is located 1.5 blocks from the lake and is less than a 10 minute drive to Lake Geneva. Featuring an outdoor hot tub, gated backyard and an amazing basement bar. Spend the afternoon shopping and enjoying the many activities the area has to offer. Spend the evening with a cocktail in the 4 person hot tub on the deck or have some s'mores by the firepit.

Home in Waukegan

4.97 out of 5 average rating, 151 reviews

The Brick Arch

We are excited to welcome you to this comfortable and newly renovated charming home in the perfect location if you're visiting Northern Illinois/Chicago. Come see why Waukegan is nicknamed "Green Town" and is home to some of the finest parks, ravines, and walking trails. With an incredible sandy beach, lakefront, galleries, breweries, restaurants, and more, it is definitely a place to check out! We are very close to Six Flags, Great Lakes Naval Base, and The Genesee Theatre too!

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 Elgin

4.88 out of 5 average rating, 113 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.

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Popular amenities for Highland Park house rentals

Free parking on premises

Air conditioning

House rentals with a pool

Home in Lake Geneva

4.93 out of 5 average rating, 14 reviews

Woodhaven, a Luxury Lake Geneva HotTub-Pool Estate

Home in Lake Geneva

5 out of 5 average rating, 26 reviews

Cozy cabin getaway near Lake Como and Lake Geneva

Home in Bloomingdale

4.94 out of 5 average rating, 35 reviews

Whole House with a Hot Tub!

Home in Lake Geneva

5 out of 5 average rating, 4 reviews

Private In-Ground Pool |Hot Tub |1.5 Acre Home

Home in Schaumburg

4.83 out of 5 average rating, 12 reviews

Schaumburg Oasis with a Pool and Hidden Garden

Home in Genoa City

5 out of 5 average rating, 49 reviews

Winterful Life: S’mores & Skiing near Lake Geneva

Home in Lake Forest

4.9 out of 5 average rating, 63 reviews

Beautiful 137 Year Old Farm Home (3night min)

Home in Schaumburg

4.95 out of 5 average rating, 20 reviews

Paradise 4BR w/ Pool & Games

Weekly house rentals

Home in Northbrook

4.98 out of 5 average rating, 47 reviews

*King bed *Outdoor Living *Sought-After Area

Home in Highland Park

4.96 out of 5 average rating, 96 reviews

Charming Ranch-Style Cottage

Home in Norwood Park

4.96 out of 5 average rating, 107 reviews

3BD Home Mins from Airport | Free Wi-Fi + Parking

Home in Highland Park

4.89 out of 5 average rating, 54 reviews

A Wonderful Getaway Home on the North Shore!

Home in Highland Park

5 out of 5 average rating, 28 reviews

Sanctuary on the Ravine

Home in Waukegan

4.98 out of 5 average rating, 102 reviews

Charming Brick Tudor with Modern Upgrades

Home in Highland Park

4.92 out of 5 average rating, 49 reviews

Witness Sunrise Over Lake Michigan

Home in Highland Park

4.85 out of 5 average rating, 40 reviews

Modern Luxe Home w/Gameroom and Electric Fireplace

Private house rentals

Home in Arlington Heights

4.94 out of 5 average rating, 66 reviews

Casa Blanca, 5 Beds

Home in Lake Bluff

4.93 out of 5 average rating, 27 reviews

3 bedroom, living & family room, screened porch

Home in Lake Forest

5 out of 5 average rating, 7 reviews

Home in East Lake Forest

Home in Skokie

4.88 out of 5 average rating, 84 reviews

Luxe-Haus of Love—The 1938 Cape Cod |Heated FLRS |

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 Palatine

4.85 out of 5 average rating, 46 reviews

Private Room w/ attached bath and personal kitchen

Home in Skokie

5 out of 5 average rating, 9 reviews

Unique and Historic Lustron Home

Quick stats about house rentals in Highland Park

Total rentals
30 properties
Nightly prices starting at
$40 before taxes and fees
Total number of reviews
1.3K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace

Destinations to explore