Vacation rentals in Pistakee Highlands

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Top-rated vacation rentals in Pistakee Highlands

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Top guest favorite

A cozy seating area is presented with two sofas adorned with decorative pillows. A large lamp with a blue shade complements the space, while light filters through the large windows, enhancing the bright atmosphere. A piece of wall art and natural accents are also visible.

Home in Salem

4.93 out of 5 average rating, 101 reviews

Center Lake View Cottage, near Camp&Silver Lakes

Relax & enjoy your stay in this peaceful home in quiet, friendly neighborhood. Launch your boat in Center Lake at end of street or visit one of many lakes nearby. Camp Lake less than 2 minutes away, close to Silver Lake and others. This home has an awesome sled hill, fire pit with seating area, and a relaxing deck with lake views. Close to Wilmot Mountain, Lake Geneva, & Bristol Renaissance Faire. 25 mins to Six Flags or Lake Geneva, 1 hr to Chgo or Milwaukee. 35 mins to Great Lakes Naval Base

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, 140 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.

Superhost

A bright bedroom features a spacious bed with a light blue quilt and accented by a colorful wooden headboard. A desk with a chair is positioned next to a small seating area. Natural light enters through a window draped with a light gray curtain.

Cabin in Spring Grove

4.82 out of 5 average rating, 62 reviews

Enjoy a Getaway @ The Lake-Heim by Chain-O-Lakes

Enjoy a comfy retreat in this cute 1BR home nestled right next to Grass Lake, IL. Newly updated shower. A lovely space to unwind by the lake whether it is work or play. Awake to a quiet morning, ready for a day of water activities with impressive views. Early risers can catch a sunrise to die for. Indulge in the comfort and tranquility of this lakehouse cabin. 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 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

4.87 out of 5 average rating, 23 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 image captures a serene lake view during sunset, reflecting warm hues of orange and pink on the water's surface. A private dock extends into the lake, flanked by several posts, with a small floating platform visible nearby.

Home in Fox Lake

4.9 out of 5 average rating, 21 reviews

Nippersink Lakehouse-Private Pier & Pet friendly!

A perfect gateway home for the family or a small group. The beautiful sunset can be viewed from the raised deck or the private pier. There are 2 jet ski ramps and room for boat parking, so bring your water toys and enjoy this amazing boating vacation property. Nippersink lake is right in the middle of the 13 interconnected lakes that makes up the amazing chain of lakes. Enjoy fishing, utilizing the 4 provided kayaks or stand-up paddle boards upon request for unlimited water fun.

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, 194 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 !

Top 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, 189 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.

Guest favorite

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, 137 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, 160 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 living area is captured, featuring a large sectional sofa arranged around a circular coffee table. A textured area rug covers the floor, and natural light fills the space from the multiple windows. A ceiling fan and a wall-mounted television add functionality, while decorative elements enhance the cozy ambiance.

Apartment in Grayslake

4.95 out of 5 average rating, 66 reviews

Apartment in Downtown Grayslake

Welcome to downtown Grayslake! Enjoy your stay in our quaint one-bedroom apartment overlooking Center Street. Nestled above our lifestyle boutique, 27 Houses, you can enjoy everything our adorable town has to offer. Grayslake is practically straight out of a Hallmark movie, and you'll be right in the center of everything. With a cozy floorpan, enjoy a cup of coffee, listen to some vinyl, or get right to work at our dedicated workspace. We're excited to welcome you!

Superhost

An inviting entrance to the cottage is shown, featuring a small wooden deck with two folding chairs and a table. Steps lead to a white door framed by white siding, while greenery adds a natural aesthetic to the pathway.

Home in Fox Lake

5 out of 5 average rating, 4 reviews

Lakeside Getaway 1 Bedroom

Take a break and unwind at this peaceful oasis. The holiday home features lake views, air-conditioning, and a fully equipped kitchen with a refrigerator, microwave, dishwasher, oven, and stovetop. Additional amenities include a dining area, TV, and outdoor dining space. Not far from 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).

Top guest favorite

A cozy bedroom features a plush king-sized bed with a light-colored duvet and decorative cushions. Natural light enters through large windows adorned with soft curtains. A comfortable bench sits at the foot of the bed, alongside a dark wood dresser and a small television.

Condo in Lake Geneva

4.96 out of 5 average rating, 106 reviews

The Landis @ Lake Geneva, simple elegance & charm.

Kick back and relax in this calm, elegant One bedroom Villa with a KING size bed. This vacation rental is in a quiet area of Lake Geneva, but just minutes from all the vibrancy of downtown Lake Geneva or Williams Bay. It is within walking distance to Mars Resort, The Getaway or The Ridge. This is a perfect spot for couples looking for a relaxing getaway. Local laws require all guests names and address be provided prior to check in.