Vacation rentals in Oakwood Hills

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Top-rated vacation rentals in Oakwood Hills

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Guest favorite

Loft in West Dundee

4.97 out of 5 average rating, 441 reviews

Hip Urban Loft - Small Town Charm - 124 LOFTS #2

Luxury one-bedroom loft in the heart of downtown Dundee. Newly renovated 125-year-old building with timber ceilings, exposed brick walls and beautifully restored hardwood floors. Tastefully decorated and features a king-size Beautyrest mattress, luxury bed linen, private bathroom, kitchenette with under counter refrigerator, Kuerig coffee maker and lightning fast Wi-Fi for streaming your favorite shows on the 60” LED smart TV. 124 LOFTS offers 4 separate luxury lofts. Loft 2 is our most spacious

Jan 18 – 25

G$28,513 GYD per night

Guest favorite

Home in McHenry

5.0 out of 5 average rating, 10 reviews

Relaxin' on the River

Relaxing & updated waterfront home ON the Fox River, peaceful countryside setting! Home has an oversized deck, patio, firepit & pier. Updated , 4 beds split between 2 bedrooms, 1 full bath. Great for a weekend or month-long getaway. Updated kitchen, bathroom, flooring, roof, HVAC. Fenced in front yard is pet friendly. Washer & Dryer. The deck in back as great views of the river. Patio & firepit with chairs. 9-10 minute drive from downtown McHenry where you'll have shops, restaurants, Walgreens!

Jun 11 – 18

G$47,980 GYD per night

Guest favorite

Apartment in McHenry

5.0 out of 5 average rating, 69 reviews

Walk to downtown McHenry @ the heart Fox River

2nd. floor. Few blocks walk east/south to most of the fun, restaurants, bars McHenry has to offer. Across the street from a Pokémon Gym @ Veterans Park. Cozy, with full kitchen, games, toys & extra amenities to make your stay relaxing & comfortable. Fenced backyard. Smoking only outside. 4:20 allowed in backyard & not in view of under the age of 21. 1 block west of the Fox River includes 488 miles of shoreline of the Chain of Lakes. Free boat/kayak launch minutes away. NO PETS ALLOWED

Dec 12 – 19

G$30,045 GYD per night

Guest favorite

Guesthouse in Hampshire

4.95 out of 5 average rating, 39 reviews

Shiloh Place - Two Minutes Off The Highway

This stylish studio with all the amenities is two minutes off I-90 and just behind Dell Webb in Huntley. A 10 minute drive from the newly built Amazon facility Newly furnished and freshly painted, it features a full size kitchen, separate dining area with a private keyless entrance Sleeps up to four comfortably, featuring a king size memory gel foam mattress with luxurious bedding. Enjoy a 55” TV from the day bed that also opens to a double. The space is very suitable for short or long stays

Sep 5 – 12

G$18,460 GYD per night

Guest favorite

Home in Crystal Lake

4.88 out of 5 average rating, 8 reviews

Stunning 12-person Home ~Game Room~Pet Friendly

This special place is close to everything, making it easy to plan your visit. Escape to our newly renovated 4BD,2½ Bath modern home in Crystal lake,Illinois. Ideal for families or groups, this spacious abode boasts 4cozy bedrooms, 2.5 bathrooms, and a host of entertainment options including a pool table,and TVs in every room. Enjoy a serene stay in a peaceful neighborhood, with all the conveniences necessary for a memorable vacation. ✔ 4 Comfortable Bedrooms ✔ 2½ Bathrooms ✔ Fully Equipped

May 5 – 12

G$53,260 GYD per night

Guest favorite

Guesthouse in McHenry

4.95 out of 5 average rating, 155 reviews

"The Apartment" in the heart of downtown McHenry

We welcome you to be our guest in this charming, historic home built in 1911 by a German mason. This upper unit Apartment is a spacious 1,100 square feet, lovingly restored with a vintage aesthetic in 2018. The private entrance to "The Apartment" will lead you to; 2 cozy bedrooms & 1 vintage inspired yet modern bath with walk in shower. A large living room, dining area and bright clean kitchen will make you feel right at home. 9 foot ceilings and tons of natural light through out.

Dec 14 – 21

G$28,482 GYD per night

Guest favorite

Townhouse in Hoffman Estates

4.91 out of 5 average rating, 291 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.

Jan 8 – 15

G$20,309 GYD per night

Guest favorite

Apartment in Cary

5.0 out of 5 average rating, 155 reviews

A Peaceful Get-Away

Come and enjoy the quiet of nature. We are located off the beaten path, near the Fox River, but less than three miles from the Metra station (into Chicago); and less than five miles from the Norge Ski Club. Within driving distance, there are golf courses, hiking paths, and shopping. Our fully furnished apartment is attached to our main house and offers you a private entrance and driveway parking for one vehicle.

Feb 3 – 10

G$26,441 GYD per night

Guest favorite

Cottage in Fox River Grove

4.94 out of 5 average rating, 49 reviews

Little Fox Cottage - A Cozy Riverview Getaway

A cozy getaway in the Northwest Suburbs of Chicago. Located 40 miles from the city and just 1.25 miles from the Fox River Grove Metra stop. Get away from the city or 'work from home' in our 1 bedroom cottage with a giant covered outdoor space tucked against the slope of a beautifully terraced hill.

Sep 16 – 23

G$35,328 GYD per night

Guest favorite

Condo in Crystal Lake

4.87 out of 5 average rating, 172 reviews

Crystal Lake newly updated, walk to beach

We are just minutes from historic downtown and just a few blocks away from Crystal Lake’s beautiful beach. We are block from Route 14 and within walking distance to several restaurants, library and some shopping. Perfect for a long relaxing weekend getaway.

Oct 4 – 11

G$24,147 GYD per night

Guest favorite

Home in Cary

4.81 out of 5 average rating, 53 reviews

Spacious 3 Bedroom

Entire top level of a bi-level home! Bottom level is a separate unit with separate entrance in front and back, not part of this listing Enjoy evenings around the fire pit or relaxing on the balcony. Please message with any questions.

Jul 21 – 28

G$63,468 GYD per night

Guest favorite

Apartment in St. Charles

4.98 out of 5 average rating, 225 reviews

Quiet Getaway Near Fox River (Listing 1)

Listing 1 is 3 room upstairs apartment with private entrance and small deck. Quiet neighborhood. Beautiful yard, pond and patio. Enjoy game of chess on our outdoor chess board. No pets please. No exceptions.

Sep 18 – 25

G$24,799 GYD per night