Vacation rentals in Pistakee Highlands

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Top-rated vacation rentals in Pistakee Highlands

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Top guest favorite

A two-story house is presented with a welcoming blue front door and bright flower pots lining the entrance. The property is surrounded by neatly maintained grass and pathways, with trees and shrubs adding greenery to the inviting façade.

Apartment in McHenry

5 out of 5 average rating, 136 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 favorite

A spacious outdoor patio features a wooden dining table surrounded by six matching chairs. Two colorful kayaks are mounted on the wall, while a private dock extends into the water, providing access for boating and fishing.

Home in McHenry

4.91 out of 5 average rating, 22 reviews

2 kayaks Game room Firepit BBQ grill Netflix WiFi

Escape to our peaceful lakeside retreat, perfect for both relaxation and adventure. With direct lake access, enjoy kayaking, fishing, or simply taking in the views. Inside, an open-concept living area, beautiful kitchen, sunroom, and game room offer cozy spaces for relaxation and fun for the whole family. Outside, unwind on the patio or explore the lake from the private dock. Ideal for reconnecting with nature and loved ones, this retreat offers a serene escape from the hustle of city life.

Guest favorite

The king bed is presented with a white linen cover and flowery pillows, situated in a serene, softly lit room. A cedar barrel sauna, made of warm-toned wood, is shown outside among trees. The waterfront features a wooden dock extending towards the calm lake, surrounded by autumn foliage.

Home in Spring Grove

4.92 out of 5 average rating, 79 reviews

Pelican LakeHouse w/boat slip & sauna (sleeps 4)

Relax in the peaceful lakeside “Pelican House”. Has updated kitchen, vaulted ceiling, lake view, king bed & queen sleeper. A great lake property for family fun, friends trip or romantic getaway. 350' of waterfront with 2 small beaches, floating piers & more. Swim, boat, ski & fish or take in the changing seasons from the sauna. We are in nature. Expect spiders, webs, bees, ants & mosquitoes. Though we clean just hours before your stay spiders can & will spin a web in that short time.

Superhost

A vibrant blue cabin is positioned alongside a gravel path, framed by lush greenery and ornamental grasses. Soft string lights are strung along the exterior, creating a warm ambiance. Large glass doors provide a view into the inviting interior, set against a backdrop of a serene evening sky.

Cabin in Spring Grove

4.9 out of 5 average rating, 20 reviews

Spacious 2BR Cabin@The Lake-Heim

Enjoy a quiet family vacation at this peaceful lakefront cabin. Homely 2BR/1BA cabin (Unit #1 with two queen beds and queen-size sofa bed) with direct lake view next to Grass Lake at Chain-O-Lakes. Start the morning with a breathtaking sunrise and enjoy the afternoon with fun-filled water activities with the family by the dock and the floating deck. We conduct regular pest treatment to keep pests away, but being close to nature and the lake, expect occasional bugs in warmer weather.

Superhost

A wooden deck is presented, furnished with a glass-top table and several chairs. Sunlight filters through nearby trees, illuminating the space. Kayaks and paddleboards are arranged along the shore, visible in the background, creating a connection to the outdoor activities offered by the lake.

Home in Fox Lake

5 out of 5 average rating, 3 reviews

Lakeside Getaway 2 King Beds

Our lake front cottage is the perfect retreat from day to day life. 2 large bedrooms with king beds and a full bathroom give room for two couples or a family. The living has a sofa sleeper and gorgeous lake views. Fully stocked kitchen as well Located close to Chicago O'Hare International Airport (36 mi), Six Flags Great America (14 mi), Naval Training Center, Great Lakes (22 mi), and Raging Buffalo Snowboard Ski Park (23 mi). Guests can also enjoy skiing and other activities

Guest favorite

A spacious living area is highlighted by large windows offering views of the water. Colorful seating options, including bean bags and patterned chairs, complement a wooden coffee table. Sleek ceiling fixtures and a soft rug define the gathering space, enhancing the open layout.

Home in Richmond

4.95 out of 5 average rating, 193 reviews

TheGlassCabin@HackmatackRetreat

The Pond House, a vintage glass cabin filled with art, water views & eclectic vibes privately perched on the sacred grounds of Hackmatack Retreat Center. Native prairie, a winding slow river, two ponds, 200+ year old oaks & big sky- Countless places to curl up, gathering, focus-- nooks and crannies indoors and out, we offer “time out for time in” amidst this noisy world. Minutes from 2 small towns, all amenities, we're all about peace & ease-- let us custom curate your experience !

Guest favorite

A historic stone home built in 1911 is prominently featured, showcasing its grand architectural details. The façade includes a porch supported by strong columns. A group of individuals stands in front, illustrating the home's welcoming presence in its early days amidst a natural landscape.

Guesthouse in McHenry

4.96 out of 5 average rating, 185 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.

Superhost

A circular stone fire pit is surrounded by several black Adirondack chairs. A vibrant fire burns brightly in the center, with a basket of firewood and a tray containing marshmallows placed nearby. The serene lake is visible in the background.

Home in Fox Lake

4.89 out of 5 average rating, 133 reviews

Spacious Lakefront Retreat | Sunset VIEW | Firepit

Welcome to Howard House by Evereste Experiences. A hidden gem on the Fox Chain o' Lakes. Situated centrally on the lakefront of beautiful Nippersink Lake just an hour outside of Chicago, this spacious and stylish retreat is located on a hill with ultimate views of the lake and stunning sunsets over the water. Located near downtown Fox Lake and the Metra train stop. With a large back deck, over 60ft of lake frontage, a dock, firepit and swimming area, you'll never want to leave!

Top guest favorite

A serene living area features a large sliding glass door leading to a deck with unobstructed views of Round Lake. Natural wood accents adorn the wall, while a plush sofa and a small coffee table create a relaxing seating space.

Home in Round Lake Beach

4.99 out of 5 average rating, 156 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 favorite

A modern kitchen features stainless steel appliances and granite countertops, with a spacious island that includes seating for four. A comfortable living area is visible in the background, showcasing a soft gray sofa and large windows with natural light filtering through.

Townhouse in Bull Valley

4.95 out of 5 average rating, 22 reviews

Elegant New Home Near Lakes - Relax & Unwind!

Welcome to your perfect getaway in Wonder Lake, IL! Nestled in a beautiful new community, our brand-new construction home offers the ultimate blend of comfort and convenience. Whether you’re here to relax by the serene lakes, coming in for work, explore picturesque walking paths, or take a short 20-minute drive to the stunning Lake Geneva, our home is the ideal base for your adventures. PLEASE NOTE CONSTRUCTION IS STILL ONGOING IN THE SURROUNDING HOMES!

Superhost

A traditional two-story house is set against a backdrop of lush green trees, with steps leading up to a spacious front deck. Several outdoor chairs surround a firepit in the foreground, while parked vehicles are visible nearby.

Home in Fox Lake

4.83 out of 5 average rating, 137 reviews

Lakefront Paradise

Relax and have fun with the family and friends at this unique getaway! We are situated directly on the lakefront with private access to our pier where you can enjoy world class sunset views. Jump in and go swimming, roast s'mores over a campfire right next to the water, grill up some burgers on the spacious deck or get some rest in our luxurious suites in this newly renovated (June 2021) home.

Guest favorite

The view from the property showcases a serene lake surrounded by lush greenery, with a boat docked at a private pier. Large trees frame the scene, while the calm water reflects the blue sky and light clouds, creating a tranquil atmosphere.

Home in Fox Lake

4.88 out of 5 average rating, 115 reviews

Lakeside paradise with Hot Tub!

Perfect summer getaway! Enjoy swimming in the Chain O’Lakes or relaxing dockside in our new gazebo, overlooking breathtaking, sunset lake views. Brand new HOT TUB, Chef’s kitchen, large living areas, outdoor fire pit, nearby restaurants and so much more! Our 3600+ sq/ft of living space: 5 bedrooms and 3.5 baths, fully finished basement!