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Pet-friendly vacation rentals in Highland Park

Find and book unique pet-friendly homes on Airbnb

Top-rated pet-friendly home rentals in Highland Park

Guests agree: these pet-friendly homes 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.

Sep. 27 – Oct. 4

$801 CAD per night

Guest favourite

Guest suite in Wood Dale

4.9 out of 5 average rating, 427 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 .

Oct. 17 – 24

$174 CAD per night

Guest favourite

Home in Berwyn

4.92 out of 5 average rating, 239 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

$148 CAD per night

Guest favourite

Guest suite in Chicago

4.93 out of 5 average rating, 353 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

Mar. 13 – 20

$206 CAD per night

Guest favourite

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.

Nov. 27 – Dec. 4

$304 CAD per night

Guest favourite

Apartment in St. Charles

4.95 out of 5 average rating, 191 reviews

Vintage Charm

Welcome to The Vintage Charm! This downstairs apartment is 2 beds & 1 bath of Vintage Charm & Cozy Warmth. The walls are plaster, the ceilings are high, the floors are mostly original oak & it speaks to comfort, warmth & the charm of gracious living from the Victorian Era! Please note that new window AC units are in place for cooling & there is a furnace for heat. Entry is via an enclosed front porch. *Artemis is my basement kitty, she's friendly-ish so be respectful *

Feb. 16 – 23

$167 CAD per night

Guest favourite

Guest suite in Zion

4.89 out of 5 average rating, 140 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

$121 CAD per night

Guest favourite

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. 2 – 9

$150 CAD per night

Guest favourite

Tiny homes in Burr Ridge

4.92 out of 5 average rating, 241 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

Nov. 2 – 9

$175 CAD per night

Guest favourite

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).

Jun. 19 – 26

$207 CAD per night

Guest favourite

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.

Jun. 26 – Jul. 3

$119 CAD per night

Guest favourite

Apartment in Forest Park

5.0 out of 5 average rating, 219 reviews

Like a Treehouse!

If you're coming to Illinois for any medical procedure that's no longer available in your home state, reach out to us about discounts. You'll feel like you're in a tree house in our 850 sq ft coach house, above our workshop/garage, behind our home in historic Forest Park (with "The Mayberriest Downtown!"- Chicago Magazine), right next to Oak Park. Just 8 miles west of Downtown Chicago, convenient to I-290 and the Blue Line train.

Oct. 2 – 9

$175 CAD 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

Guest favourite

Home in Chicago

4.89 out of 5 average rating, 332 reviews

Private 3rd Floor Apartment

Dec. 1 – 8

$222 CAD per night

Guest favourite

Home in Round Lake Beach

4.89 out of 5 average rating, 151 reviews

Corner Lakefront Property

Feb. 26 – Mar. 5

$351 CAD per night

Home in Elgin

4.88 out of 5 average rating, 104 reviews

Charming Elgin Home with a Great Location

Oct. 3 – 10

$211 CAD per night

Guest favourite

Home in Montgomery

4.84 out of 5 average rating, 109 reviews

Nice, Private Ranch Home

Jul. 22 – 29

$237 CAD per night

Guest favourite

Home in Forest Park

4.91 out of 5 average rating, 223 reviews

Charming dog friendly 2-Bath Bungalow Near Chicago

Jun. 25 – Jul. 2

$258 CAD per night

Guest favourite

Home in Chicago

4.96 out of 5 average rating, 127 reviews

Chicago Riverhouse summer on our patio!

Oct. 23 – 30

$576 CAD per night

Guest favourite

Home in Chicago

4.86 out of 5 average rating, 215 reviews

The Avondale Guesthouse

Feb. 5 – 12

$175 CAD per night

Guest favourite

Home in Antioch

4.9 out of 5 average rating, 106 reviews

Lakefront, beautiful views, spacious and private.

Oct. 15 – 22

$806 CAD per night

Pet-friendly home rentals with a pool

Apartment in Itasca

4.77 out of 5 average rating, 181 reviews

King Bed at Chicago Northwest + PET Friendly

Jul. 5 – 12

$228 CAD per night

Chalet in Ingleside

4.84 out of 5 average rating, 369 reviews

"A" Frame Brandenburg Lake

Oct. 23 – 30

$408 CAD per night

Guest favourite

Home in Grayslake

4.95 out of 5 average rating, 109 reviews

Huge Indoor Pool &Theater - link moved see details

Aug. 28 – Sep. 4

$1,092 CAD per night

Apartment in Chicago

4.87 out of 5 average rating, 110 reviews

Level ◆ Two Bedroom Deluxe Corner Suite + Balcony

Jan. 10 – 17

$802 CAD per night

Apartment in Chicago

4.78 out of 5 average rating, 156 reviews

Beautiful Corner 2 Bedroom in the Loop | Roof Deck

Feb. 5 – 12

$521 CAD per night

Guest favourite

Apartment in Rosemont

5.0 out of 5 average rating, 15 reviews

Relaxing Standard Room l Free Airport Shuttle

Jun. 19 – 26

$265 CAD per night

Guest favourite

Apartment in Chicago

5.0 out of 5 average rating, 7 reviews

Cozy studio near Michigan lake

Jul. 9 – 16

$243 CAD per night

Guest favourite

Home in Grayslake

5.0 out of 5 average rating, 15 reviews

Family-sized Indoor Heated Pool & Movie Theater!

Mar. 8 – 15

$1,261 CAD per night

Private, pet-friendly home rentals

Guest favourite

Apartment in Chicago

4.95 out of 5 average rating, 106 reviews

Comfortable, modern apartment 20 Min from Downtown

Jan. 24 – 31

$213 CAD per night

Guest favourite

Apartment in Wilmette

4.89 out of 5 average rating, 235 reviews

Spacious Garden Apartment with Sauna and Fireplace

Jul. 15 – 22

$386 CAD per night

Guest favourite

Apartment in Chicago

4.96 out of 5 average rating, 237 reviews

Roscoe Village One Bed Lux Apartment Near Wrigley

Nov. 3 – 10

$194 CAD per night

Guest favourite

Apartment in Oak Park

4.91 out of 5 average rating, 104 reviews

Lovely, spacious 2bd, 1bath home w/free parking

Oct. 1 – 8

$215 CAD per night

Cottage in Antioch

4.85 out of 5 average rating, 221 reviews

#5 Tiny Lake Cottage at Cypress Resort & Marine

Dec. 11 – 18

$179 CAD per night

Apartment in Chicago

4.86 out of 5 average rating, 101 reviews

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

Apr. 4 – 11

$154 CAD per night

Guest favourite

Apartment in Chicago

4.89 out of 5 average rating, 177 reviews

Historic Chicago neighborhood flat

Nov. 10 – 17

$208 CAD per night

Apartment in Forest Park

4.92 out of 5 average rating, 112 reviews

Village Cottage - Forest Park Studio Pets 72142F

May 9 – 16

$189 CAD 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
$109 CAD before taxes and fees

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