Title: Highwood Vacation Home Rentals from CA $102: Search Top Private Vacation Homes for Rent | Expedia.ca [Hotels in Highwood](https://expedia.ca/Highwood-Hotels.d115190.Travel-Guide-Hotels)[Vacation Rentals in Highwood](https://expedia.ca/Highwood-Vacation-Rentals.d115190.Travel-Guide-VacationRentals)[Highwood Car Rentals](https://expedia.ca/Car-Rentals-In-Highwood.d115190.Car-Rental-Guide)[Highwood Vacation Packages](https://expedia.ca/Highwood.d115190.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/f2636ab6e196d52ecb4914781112e2c5.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Tara Jabbari # Highwood Vacation Rentals ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates In two weeks [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=115190&startDate=2025-10-17&endDate=2025-10-19&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=115190&startDate=2025-10-31&endDate=2025-11-02&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=115190&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=115190&startDate=2025-12-26&endDate=2025-12-28&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Highwood Vacation Homes ![Desk, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/116000000/115780000/115775200/115775130/e4656d3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/116000000/115780000/115775200/115775130/aeb07003.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/116000000/115780000/115775200/115775130/c554d00c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/116000000/115780000/115775200/115775130/ec6df83e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Relaxing Chicago Studio Edgewater 10/10 Exceptional (17) "Had a great stay. Great location. " CA $133 CA $276 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Chicago-Hotels-Relaxing-Chicago-Studio.h115775130.Hotel-Information) ![1 bedroom, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793099/70ad4f1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793099/ec8e37d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793099/0523bb1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116793100/116793099/bbcd29f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Prime City Stay in a 1BR Apt Irving Park 9.2/10 Wonderful (10) "Location is very good, 10 mins walk to irving blue line station, and the apartment has lot of light during the day as it was a corner unit." CA $102 CA $252 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Chicago-Hotels-Prime-City-Stay-In-A-1BR-Apt.h116793099.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792828/d6084ece.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792828/a5b828c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792828/b7ff7525.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792900/116792828/dd022100.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy & Furnished 2BR Unit Ravenswood 9.6/10 Exceptional (8) CA $123 CA $297 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Chicago-Hotels-2BR-Radiant-Urban-Apartment.h116792828.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/117000000/116750000/116740900/116740866/f9f5b2d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, foosball, computer monitors](https://images.trvl-media.com/lodging/117000000/116750000/116740900/116740866/2e144bff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/117000000/116750000/116740900/116740866/4d31dd6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, foosball, computer monitors](https://images.trvl-media.com/lodging/117000000/116750000/116740900/116740866/721a7cf9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Theater • Game Room • Gym • Firepit • 4BR Home Belmont Cragin 7.6/10 Good (10) "Comfy beds and a great house for kids and adults." CA $94 CA $712 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Chicago-Hotels-4BR-Retreat-W-Theater.h116740866.Hotel-Information) ![Fridge, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792702/7dc7e59d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792702/42fd77c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792702/a41342cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116792800/116792702/df2ce2a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chic Studio in Heart of Chicago Portage Park 10/10 Exceptional (2) "Older property. Landlord special in the bathroom. Definitely needs better window coverings. Otherwise, comfortable, safe, and clean. " CA $115 CA $268 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Chicago-Hotels-Chic-Studio-In-Heart-Of-Chicago.h116792702.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/115000000/114390000/114385300/114385207/9f3e1d39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/115000000/114390000/114385300/114385207/be3e8c55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/115000000/114390000/114385300/114385207/2549efd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/115000000/114390000/114385300/114385207/101d8bcc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Elegant Style Loft Montrose|13 mins DT|4 mins Lake Uptown 7.4/10 Good (3) "Beautiful apartment in a wonderful building. There were great restaurants and AC was great on a very hot weekend." CA $67 CA $255 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Chicago-Hotels-Elegant-Style-Loft-Montrose-Beach-Rooftop-WFH-Gym.h114385207.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/118000000/117890000/117881900/117881842/8006c795.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117890000/117881900/117881842/b5843f1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117890000/117881900/117881842/f3da79bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave](https://images.trvl-media.com/lodging/118000000/117890000/117881900/117881842/d04beb93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tiny Home Retreat with hot tub Lake Villa 8.8/10 Excellent (3) "NICE PLACE, NICE NEIGHBORHOOD" CA $208 CA $459 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Lake-Villa-Hotels-Tiny-Home-Retreat-With-Hot-Tub-Out-In-Nature.h117881842.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/118000000/117520000/117513700/117513666/w1288h972x1y0-9ea5d5f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/118000000/117520000/117513700/117513666/w1288h954x1y0-c2d1d8ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/118000000/117520000/117513700/117513666/w1288h941x1y0-771b8cc2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117520000/117513700/117513666/w1288h958x1y0-81554e20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chic apartment with fitness room and AC in beautiful Chicago Rogers Park 6.8/10 (3) "Didn’t receive check in information until after book in time. This was after repeated messages, calls to property manager & VRBO. The actual apartment was tidy, however the drain in the tub was clogged. Parking was difficult and when asked if we could park in the lot behind the apartment, we were told it was 20 more a day. Was allowed to park there the second night at no cost. Communication once we were actually checked in was good. It’s in a lovely neighborhood and close to the train and... CA $91 CA $360 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Chicago-Hotels-Chic-Apartment-With-Fitness-Room-And-AC-In-Beautiful-Chicago.h117513666.Hotel-Information) ![1 bedroom, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116792400/116792370/77ba8bc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792400/116792370/614f0803.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116792400/116792370/f698a154.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/117000000/116800000/116792400/116792370/2629eaef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Peaceful 1BR Escape in Evanston South Evanston 8.0/10 Very good (5) "Quiet, clean and spacious! A peaceful neighborhood. " CA $119 CA $267 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Chicago-Hotels-Peaceful-1BR-Escape-In-Evanston.h116792370.Hotel-Information) ![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/117000000/116800000/116792400/116792368/1d35e5cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116792400/116792368/a1d7f9ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116792400/116792368/61f68dfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116792400/116792368/501017c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 1-Bedroom Pad | Cozy + All-Set Skokie 10/10 Exceptional (1) "This was a great space. The location was perfect and we had everthing we needed. We would definitely stay here again. " CA $118 CA $266 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Chicago-Hotels-1-Bedroom-Pad-Cozy-All-Set.h116792368.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793112/11a2ba3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793112/56f61d6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793112/712599f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793112/fa396607.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 1BR Chic & Sunny Place Bowmanville 9.4/10 Exceptional (3) "Location was perfect for visiting family and getting around the city. Bed was extra comfy and the AC worked wonderfully. Will stay here again on our next visit. " CA $102 CA $252 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Chicago-Hotels-1BR-Chic-Sunny-Place.h116793112.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/115000000/114670000/114666300/114666210/6385a4ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/115000000/114670000/114666300/114666210/d60dd8ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/115000000/114670000/114666300/114666210/d7857ebb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, towels, soap, shampoo](https://images.trvl-media.com/lodging/115000000/114670000/114666300/114666210/22c26f54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC Barrington 10/10 Exceptional (1) "Our experience at this place was unique; the best relaxing get away I have had in many years. From check-in to total comfort and cleanliness to privacy and coziness. And “Friends-Themed”accents made our stay specially touching. It was a delight walking downtown to great restaurants and stores while admiring beautifully maintained new and old architectural gems that made us feel both amazed and nostalgic. And more than anything, a town we felt safe and welcomed everywhere. It is for sure one of... CA $176 CA $292 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Barrington-Hotels-FRIENDS-Inspired-Studio-In-Beautiful-Barrington-With-WiFi.h114666210.Hotel-Information) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793114/18cda2ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793114/ad056da4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793114/92789d2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793114/acdb160f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 1BR Gem by Shops & Dining Portage Park 2.0/10 (1) "DO NOT STAY - BEDBUGS IN THE APARTMENT. We booked for 4 nights and only stayed for 2 because there were bedbugs in the bed and we were bitten during our stay. Beware - since this is a third party property VRBO will not give you a refund. When asked about the bedbug traps they said they have never had issues, but then changed the story to say bedbugs are expected. We only saw dead ones but had bites after the 2 day stay! This was over a month ago and have not had any resolution - host will just... CA $102 CA $252 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Chicago-Hotels-1BR-Gem-By-Shops-Dining.h116793114.Hotel-Information) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792945/c9324d98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792945/fcd2f6eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792945/71c91f6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793000/116792945/c8480aa1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Homey 1BR Space Apartment Ravenswood 9.4/10 Exceptional (6) "This was a wonderful base for the days I spent exploring Chicago. The apartment is clean and comfy and it is located right on the 'L' Brown line in a charming and vibrant neighborhood. I could zip to anywhere in the city I wanted on the L and felt very relaxed coming "home" each night." CA $105 CA $255 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Chicago-Hotels-Light-Filled-1-Bedroom-Apt.h116792945.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89820000/89818200/89818126/d6cd217f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89820000/89818200/89818126/d8d4beb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/90000000/89820000/89818200/89818126/a023af49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/90000000/89820000/89818200/89818126/fc76a654.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Getaway Near ORD With Great Local Amenities Des Plaines 8.8/10 Excellent (3) "Very nice and clean place to stay at. Great communication from property manager. I would absolutely stay here again!" CA $101 CA $381 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Chicago-Hotels-Getaway-Near-ORD-With-Great-Local-Amenities.h89818126.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/49000000/48960000/48959700/48959659/591973f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/49000000/48960000/48959700/48959659/76fecaef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/49000000/48960000/48959700/48959659/3a6b662e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/49000000/48960000/48959700/48959659/61fb0165.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Master qtr close to nature & easy urban facilities Riverwoods 9.8/10 Exceptional (67) "Beautiful, quiet space." CA $138 CA $272 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Chicago-Hotels-Master-Qtr-Close-To-Nature-Easy-Urban-Facilities.h48959659.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793118/9fcd9cc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793118/f511a20e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793118/eec54680.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793118/7a4fe0f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Great Layout – Spacious 2BR Apt Rogers Park 10/10 Exceptional (4) "Clean, comfortable, and would definitely stay again!" CA $131 CA $307 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Chicago-Hotels-2BR1BA-North-Shore-Nest.h116793118.Hotel-Information) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793164/8d04619e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793164/9a443876.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793164/db996715.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/117000000/116800000/116793200/116793164/82390747.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfortable 2BR Chicago Apt Albany Park 9.6/10 Exceptional (4) "Perfect location for our trip. Very functional and comfortable. " CA $140 CA $317 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Chicago-Hotels-Comfortable-2BR-Chicago-Apt.h116793164.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106680000/106679200/106679107/a8db328b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/107000000/106680000/106679200/106679107/3ba9f44f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/107000000/106680000/106679200/106679107/8537cde7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, offices](https://images.trvl-media.com/lodging/107000000/106680000/106679200/106679107/f947f5fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pool Table, Grill & Patio | LCP Collection Beach Park 10/10 Exceptional (2) "Very clean, peaceful and accommodating" CA $357 CA $804 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Beach-Park-Hotels-Pool-Table.h106679107.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118080000/118074500/118074409/714688e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/119000000/118080000/118074500/118074409/2529121c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/119000000/118080000/118074500/118074409/53707240.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/119000000/118080000/118074500/118074409/d2a4fb64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### North Chi retreat – Navy, Sauna, Tiki Bar, Games North Chicago 9.8/10 Exceptional (9) [](https://www.expedia.ca/Chicago-Hotels-Modern-Upgrade-Near-Navel-Base-Sauna.h118074409.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-10-17&endDate=2025-10-18®ionId=115190&adults=2&lodging=VACATION_HOME&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FHighwood-Private-Vacation-Homes.d115190-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FHighwood-Private-Vacation-Homes.d115190-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Highwood Hotel Reviews ![Hyatt Regency O'Hare Chicago](//images.trvl-media.com/lodging/1000000/10000/5500/5403/46cc150a_y.jpg) ### Hyatt Regency O'Hare Chicago 10/10 Excellent "Very nice hotel. Rooms are clean" [](https://expedia.ca/Chicago-Hotels-Hyatt-Regency-OHare-Chicago.h5403.Hotel-Information) ![Hilton Chicago O'Hare Airport](//images.trvl-media.com/lodging/1000000/10000/8100/8058/ce2102d4_y.jpg) ### Hilton Chicago O'Hare Airport 10/10 Excellent "Breakfast coffee was not hot at all. Breakfast servers aren’t attentive enough. Other than that, everything was good." [](https://expedia.ca/Chicago-Hotels-Hilton-Chicago-OHare-Airport.h8058.Hotel-Information) ![Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG](//images.trvl-media.com/lodging/1000000/30000/20400/20348/9004f7ac_y.jpg) ### Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG 10/10 Excellent "Na" [](https://expedia.ca/Chicago-Hotels-Crowne-Plaza-Hotel-Chicago-OHare.h20348.Hotel-Information) ![Sonesta Simply Suites Chicago O'Hare Airport](//images.trvl-media.com/lodging/1000000/330000/328600/328524/c5f12fbd_y.jpg) ### Sonesta Simply Suites Chicago O'Hare Airport 10/10 Excellent "Good." [](https://expedia.ca/Chicago-Hotels-Sonesta-Simply-Suites-Chicago-OHare.h328524.Hotel-Information) ![DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove](//images.trvl-media.com/lodging/1000000/10000/6600/6545/8dd24dc8_y.jpg) ### DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove 10/10 Excellent "The room was perfect: very clean and nicely appointed. The staff were friendly and helpful. Airplanes taking off from O’Hare will create some noise but it is not too bad. 9.5/10" [](https://expedia.ca/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-Wood-Dale-Elk-Grove.h6545.Hotel-Information) ![Marriott Chicago O'Hare](//images.trvl-media.com/lodging/1000000/10000/300/281/13bbda80_y.jpg) ### Marriott Chicago O'Hare 10/10 Excellent "Good " [](https://expedia.ca/Chicago-Hotels-Marriott-Chicago-OHare.h281.Hotel-Information) ![Comfort Suites Chicago O'Hare Airport](//images.trvl-media.com/lodging/1000000/670000/665000/664918/f3b451c4_y.jpg) ### Comfort Suites Chicago O'Hare Airport 10/10 Excellent "Clean comfortable room with multiple dining options in walking distance" [](https://expedia.ca/Chicago-Hotels-Comfort-Suites-Schiller-Park-Chicago-OHare-Airport.h664918.Hotel-Information) ![Hyatt Place Chicago/O'Hare Airport](//images.trvl-media.com/lodging/1000000/30000/23000/22991/9622d90a_y.jpg) ### Hyatt Place Chicago/O'Hare Airport 10/10 Excellent "Staff at the front desk were very helpful and had great welcoming personalities. Room was clean. Everything was easy to get to that I needed around the area. " [](https://expedia.ca/Chicago-Hotels-Hyatt-Place-ChicagoOHare-Airport.h22991.Hotel-Information) ![Holiday Inn Chicago North-Evanston by IHG](//images.trvl-media.com/lodging/1000000/10000/5400/5356/a2066909_y.jpg) ### Holiday Inn Chicago North-Evanston by IHG 10/10 Excellent "Staff great" [](https://expedia.ca/Chicago-Hotels-Holiday-Inn-Chicago-North-Evanston.h5356.Hotel-Information) ## Find out more about Highwood ## Highwood Vacation Homes information | Number of reviews | 19,966 | | --- | --- | | Accommodation | 328 Vacation Homes | | Lowest Price | CA $102 | | Highest Price | CA $186 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [5 Star Hotels in Lake Forest](https://www.expedia.ca/5Star-Lake-Forest-Hotels.s50-0-d8508.Travel-Guide-Filter-Hotels) - [Hotels with Wifi in Bannockburn](https://www.expedia.ca/Bannockburn-Chicago-Hotels-Hotel-With-Wifi.0-n601901-0-tHotelwithwifi.Travel-Guide-Filter-Hotels) - 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