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Pet-friendly vacation rentals in Highland Park

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Top-rated pet-friendly home 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 7 – 14

ﺩ.ﺇ1,938 per night

Guest suite in Wood Dale

4.9 out of 5 average rating, 430 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 .

Jul 16 – 23

ﺩ.ﺇ481 per night

Guest suite in Chicago

4.93 out of 5 average rating, 354 reviews

Peaceful Portage Park Apartment

You have the entire apartment all to yourself (kitchen, bathroom, 2 bedrooms and an office). Shared backyard. Portage park is located about halfway between O’hare airport and downtown. It is one of the safest neighborhoods in Chicago. Parking is easy! We’re 2 blocks away from a park (dog park, playground, walking/running path, tennis courts, indoor and Olympic sized outdoor pool). Fairly close to coffee shops and good places to eat We are family friendly House trained dogs are ok : $10/night

Feb 13 – 20

ﺩ.ﺇ406 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.

Dec 25 – Jan 1

ﺩ.ﺇ747 per night

Apartment in Chicago

4.99 out of 5 average rating, 104 reviews

Newly Renovated, Spacious 2BR in Andersonville

Welcome to your newly renovated 2nd floor oasis! Located on a serene residential street, with a private parking space and backyard, this cozy retreat is nestled between the vibrant Edgewater and Andersonville neighborhoods. Indulge in a plethora of dining and entertainment options just steps away, or take a 15-minute stroll to the CTA Redline for easy access to downtown. With a bus stop right around the corner and less than 10 miles from the heart of the city, your urban adventure awaits!

Dec 7 – 14

ﺩ.ﺇ541 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!

Nov 14 – 21

ﺩ.ﺇ3,857 per night

Guest suite in Zion

4.89 out of 5 average rating, 142 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 16 – 23

ﺩ.ﺇ302 per night

Townhouse in Hoffman Estates

4.91 out of 5 average rating, 294 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.

Feb 19 – 26

ﺩ.ﺇ365 per night

Tiny home in Burr Ridge

4.92 out of 5 average rating, 243 reviews

Less is more! Pet friendly Tiny Home near Chicago!

Less is more--see for yourself how big 250 square feet can really feel! For those who would love to try tiny living and a minimalist lifestyle, this is the perfect getaway. This tiny house has everything you will need to fall in love with tiny living! There is a fenced yard, grass area for furry friends, free parking and is close to hiking trails, restaurants, shops, breweries, bars, and Chicago! Check us out on Insta: @LessIsMore_TinyHome

Mar 7 – 14

ﺩ.ﺇ409 per night

Apartment in Wilmette

4.86 out of 5 average rating, 119 reviews

Downtown Wilmette Micro Studio

During this time, we are taking extra precautionary measures to ensure our guests safety. Cute and private micro studio in phenomenal downtown Wilmette location. Steps from all local restaurants, shopping, and the Metra station. Walkable to Gillson Beach and the Linden CTA stop. Enter through the front gate to an open & shared yard with private, single access to the unit. Pets OK with additional pet fee (some breed / weight restrictions).

Jul 5 – 12

ﺩ.ﺇ504 per night

Apartment in Winthrop Harbor

4.94 out of 5 average rating, 228 reviews

Love my guests! Homey Elegant & Lake Michigan!

Large, Cozy, suite w sweet kitchenette for “portable” meals; full-size refrigerator/ freezer; a writing desk for work. Many little ( in case you forgot) items to keep you comfy. This is a quiet town on the gorgeous Lake Michigan. Near: 6 Flags, Great Lakes Navy Base; Cancer Treatment Centers of America & the city Chicago via the Metra in town. Convenient & Quiet. I have 3 dogs. They are kind, outgoing and will want to meet you.

Oct 6 – 13

ﺩ.ﺇ274 per night

Apartment in Wilmette

4.89 out of 5 average rating, 235 reviews

Spacious Garden Apartment with Sauna and Fireplace

English garden apartment in historic Wilmette home with a private entrance, sauna, washer/dryer, kitchenette, dining area, recreation room with pool table, vintage pinball machine, and a wood-burning fireplace with gas igniter. Two queen beds, 1 full-size sleeper sofa, and a single mattress are available for large families. Ideal access to Northwestern University for all events. Free WIFI and an internet-enabled flat-screen TV.

May 25 – Jun 1

ﺩ.ﺇ773 per night

Vacation rentals for every style

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Popular amenities for Highland Park pet-friendly home rentals

Free parking on premises

Air conditioning

Pet-friendly house rentals

Home in Berwyn

4.92 out of 5 average rating, 240 reviews

Private apartment with retro vibe

Sep 8 – 15

ﺩ.ﺇ349 per night

Home in Twin Lakes

4.93 out of 5 average rating, 134 reviews

Cove at 420: Modern Lake Front Home near Chicago

Oct 4 – 11

ﺩ.ﺇ2,093 per night

Home in Round Lake Beach

4.89 out of 5 average rating, 153 reviews

Corner Lakefront Property

Aug 21 – 28

ﺩ.ﺇ1,020 per night

Home in Montgomery

4.84 out of 5 average rating, 109 reviews

Nice, Private Ranch Home

Jul 8 – 15

ﺩ.ﺇ541 per night

Home in Elgin

4.89 out of 5 average rating, 105 reviews

Charming Elgin Home with a Great Location

Nov 9 – 16

ﺩ.ﺇ485 per night

Home in Chicago

4.89 out of 5 average rating, 332 reviews

Private 3rd Floor Apartment

Jan 16 – 23

ﺩ.ﺇ471 per night

Home in Forest Park

4.91 out of 5 average rating, 223 reviews

Charming dog friendly 2-Bath Bungalow Near Chicago

Jun 23 – 30

ﺩ.ﺇ578 per night

Home in Chicago

4.96 out of 5 average rating, 128 reviews

Chicago Riverhouse summer on our patio!

Mar 5 – 12

ﺩ.ﺇ1,198 per night

Pet-friendly home rentals with a pool

Chalet in Ingleside

4.84 out of 5 average rating, 369 reviews

"A" Frame Brandenburg Lake

Nov 13 – 20

ﺩ.ﺇ1,005 per night

Apartment in Itasca

4.78 out of 5 average rating, 183 reviews

King Bed at Chicago Northwest + PET Friendly

Oct 15 – 22

ﺩ.ﺇ4,271 per night

Home in Grayslake

4.95 out of 5 average rating, 109 reviews

Huge Indoor Pool &Theater - link moved see details

Jan 29 – Feb 5

ﺩ.ﺇ2,661 per night

Apartment in Chicago

4.87 out of 5 average rating, 110 reviews

Level ◆ Two Bedroom Deluxe Corner Suite + Balcony

Apr 20 – 27

ﺩ.ﺇ2,061 per night

Apartment in Chicago

4.86 out of 5 average rating, 190 reviews

Spectacular Corner 2BR Penthouse in the Loop | Roo

Dec 12 – 19

ﺩ.ﺇ1,590 per night

Condo in Fontana-on-Geneva Lake

4.76 out of 5 average rating, 164 reviews

FUN-tana All Year Round Abbey Springs Fontana WI

Oct 15 – 22

ﺩ.ﺇ930 per night

Apartment in Chicago

5.0 out of 5 average rating, 8 reviews

Cozy studio near Michigan lake

Jun 30 – Jul 7

ﺩ.ﺇ471 per night

Apartment in Rosemont

4.89 out of 5 average rating, 18 reviews

Relaxing Standard Room l Free Airport Shuttle

Aug 5 – 12

ﺩ.ﺇ1,012 per night

Private, pet-friendly home rentals

Apartment in Chicago

4.95 out of 5 average rating, 109 reviews

Comfortable, modern apartment 20 Min from Downtown

Mar 8 – 15

ﺩ.ﺇ434 per night

Apartment in St. Charles

4.95 out of 5 average rating, 191 reviews

Vintage Charm

Dec 29 – Jan 5

ﺩ.ﺇ453 per night

Apartment in Chicago

4.86 out of 5 average rating, 102 reviews

⭐️⭐️Entire Unite 2-Bdr. HORNER PARK⭐️⭐️

Apr 4 – 11

ﺩ.ﺇ304 per night

Apartment in Forest Park

5.0 out of 5 average rating, 222 reviews

Like a Treehouse!

Sep 26 – Oct 3

ﺩ.ﺇ426 per night

Apartment in Evanston

4.96 out of 5 average rating, 155 reviews

Stunning, Sunny Flat with Beautiful Backyard

Dec 28 – Jan 4

ﺩ.ﺇ1,071 per night

Home in Highland Park

4.8 out of 5 average rating, 30 reviews

Modern Luxe Home w/Gameroom and Electric Fireplace

Dec 11 – 18

ﺩ.ﺇ1,989 per night

Home in Deerfield

4.96 out of 5 average rating, 26 reviews

Lake Forest Country Estate

May 26 – Jun 2

ﺩ.ﺇ1,020 per night

Home in Highland Park

4.86 out of 5 average rating, 43 reviews

A Wonderful Getaway Home on the North Shore!

Apr 22 – 29

ﺩ.ﺇ1,123 per night

Quick stats about vacation rentals that are pet-friendly in Highland Park

Total rentals
20 properties
Wifi availability
20 properties include access to wifi
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
790 reviews
Nightly prices starting at
ﺩ.ﺇ294 before taxes and fees

Destinations to explore