Holiday houses in Oakwood Hills

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Top-rated holiday rentals in Oakwood Hills

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
Loft in West Dundee
4.97 out of 5 average rating, 492 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

Superhost
Home in Cary
4.8 out of 5 average rating, 94 reviews

KING bed | Crystal Lake | McHenry | Cary | COZY

✨Stay in the heart of McHenry County at this stylish, modern apartment!✨ Whether it’s a quick trip or an extended stay, you’ll enjoy the comfy king-sized bed, full kitchen, and large bathroom. The back patio and fire pit area are the perfect spots to relax. Plus, you’re less than a 10-minute drive to these local attractions: 🏞️Three Oaks Recreational Area 🌲Moraine Hills State Park 🏙️Downtown Crystal Lake 🏖️Crystal Lake Main Beach Experience Crystal Lake and Cary with us & learn more below!

Top Guest favourite
Apartment in McHenry
5 out of 5 average rating, 147 reviews

Walk to downtown McHenry. Heart of the Fox River

NO PETS Entire 2nd. floor. 1 block away from downtown, Fox River Riverwalk & Pokémon Gym. Full stocked kitchen, books, games, toys & extra amenities to make your stay beyond relaxing. 4:20 allowed in backyard & not in view of under the age of 21. Private smoking area in front too. Minutes away from 2 State Parks, 1 with free boat/kayak launch. Several marinas, boat rental, golf courses & huge variety of entertainment. Look at Bettye's Guidebook for more information & nearby entertainment.

Guest favourite
Apartment in Crystal Lake
4.96 out of 5 average rating, 126 reviews

Farmhouse Chic Home with a view. Downtown

Charming Historic Apartment in Downtown Crystal Lake Spacious second-floor apartment overlooking Downtown Crystal Lake, located in a vintage 1875 farmhouse. Steps away from over 100 restaurants, shops, coffee spots, and bars, all within a 2-minute walk. Enjoy updated bedding, modern comforts, and vintage finishes in a quiet space with no shared walls or upstairs neighbors. One parking space included, with additional lot park CHECKOUT OUR OTHER PROPERTIES HERE: www.airbnb.com/p/breganproperties

Top Guest favourite
Apartment in West Dundee
4.96 out of 5 average rating, 106 reviews

Charming Riverfront Stay | Heart of Downtown

Welcome to The Riverfronts! Three boutique hotel rooms perfectly situated along the river in downtown West Dundee, offering scenic views and modern comforts. ✔ Riverfront Location: Enjoy the scenic riverwalk just steps away. ✔ Prime Downtown Spot: In the heart of downtown Dundee, minutes from top attractions and dining. ✔ Exclusive Group Booking: Reserve just one or all three units for your entire party. ✔ Outdoor Firepit: Unwind by the firepit, perfect for evening gatherings. ✔ Sleeps 4: Each

Guest favourite
Home in McHenry
4.89 out of 5 average rating, 125 reviews

Highwood Haven/Indoor Pool/Hot Tub/Arcade

Unwind at Highwood Haven, an opulent McHenry getaway with a heated indoor pool and arcade. Savor culinary delights in our chef's kitchen, enjoy al fresco entertainment, and relax in sumptuous bedrooms. An hour from Chicago, it's ideal for luxury retreats and family fun. Revel in our nine-person hot tub, outdoor lounge with TV, and serene bedrooms. Make memories with both lively entertainment and tranquil moments, all within a luxurious setting. Your perfect destination for an upscale vacation.

Guest favourite
Guest suite in Riverwoods
4.95 out of 5 average rating, 427 reviews

Master qtr close to nature & easy urban facilities

This amazing prairie style home sits on 2 acre land surrounded by lush lawn and majestic oak trees - a nature lover's dream with unparalleled serenity. Vacation-like setting blends country-like quiet with nearby conveniences including shopping, trains, restaurants, highways, Ravinia (18 MINs drive). 5 MINs to I 294. 20 MINS to O'HARE; 5 Mins to Discover, Baxter; 10 MINs to Walgreens Deerfield campus, TRINITY INT'L UNIVERSITY; 15 MINS to Lake Forest Academy. 25 MINs to Great Lakes Navy Base.

Guest favourite
Apartment in Algonquin
4.8 out of 5 average rating, 130 reviews

Waterfront Stay w/ Walk to Downtown Entertainment

Apartment overlooking the Fox River. Walking distance to downtown Algonquin. Free wifi & cable TV. Don't impose on family or friends, or settle for the bland experience of a box hotel. Instead, book a comfortable stay with great amenities and enjoy the river and downtown entertainment. You'll be able to relax, get a restful sleep, and enjoy your visit. You'll also notice the little touches and the extra effort made to assure you have an awesome stay. Private Bathroom and Kitchen.

Top Guest favourite
Guesthouse in McHenry
4.96 out of 5 average rating, 194 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.

Top Guest favourite
Home in Round Lake Beach
4.99 out of 5 average rating, 167 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!

Guest favourite
Apartment in Elgin
4.8 out of 5 average rating, 180 reviews

Sherwood House

Enjoy the ambience of the Sherwood House, an 1884 Victorian built for Judge David Sherwood. Use of entire first floor apartment including a full kitchen is perfect for longer term stays. Original features include multiple stained glass windows, beautiful wood work, multiple decorative fireplaces and hardwood floors. Located just blocks from downtown Elgin, walk to shops, restaurants, the casino, bike trail or Metra. WiFi and off street parking.

Top Guest favourite
Apartment in Cary
5 out of 5 average rating, 173 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.

Popular amenities for Oakwood Hills holiday rentals

  1. Airbnb
  2. United States
  3. Illinois
  4. McHenry County
  5. Oakwood Hills