Holiday rentals in Pistakee Highlands

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Top-rated holiday rentals in Pistakee Highlands

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

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Top guest favourite
Flat in McHenry
5 out of 5 average rating, 160 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
4.83 out of 5 average rating, 72 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, 30 reviews

2 kayaks Game room Firepit BBQ grill Netflix WiFi

Wake up to snow blanketing the frozen creek and take in the peaceful winter scene from the master balcony. Gather in the open kitchen and living area—this home is made for togetherness. Challenge the family in the game room (foosball, darts, arcade), settle in for a movie night, or bundle up for s'mores by the fire pit. The sunroom offers creek views and a fireplace for quieter moments. Three bedrooms, space for 8, and a layout that keeps everyone connected. Perfect for a cozy winter retreat.

Guest favourite
The exterior of the home features a combination of stone and siding, with a spacious driveway leading to a two-car garage. The front yard is landscaped with shrubs and decorative gravel. Trees provide natural shade, while the sky displays soft orange and blue hues.
Home in Fox Lake
4.9 out of 5 average rating, 59 reviews

Waterfront - Fox Lake - Bring your boat. 3bd 2bath

Direct access to Fox Lake! This Fox Lake home provides direct lake access, while providing calm protection from wind and wake. Plenty of room to tie up your boat or rent ours while you stay. If bringing your own boat, please give us 48 hours notice. We can provide a USCG captained party pontoon excursion or a fishing trip as well. Rent our pontoon at Boatsetter. Walk to downtown restaurants, bars, billiards, shopping and movies. Three bedrooms, two full baths. Two kings, two dbl bunk beds.

Superhost
A spacious outdoor area is presented, featuring a circular stone patio with a table and chairs. A large umbrella provides shade, while a barbecue grill is situated nearby. The upper deck is visible, leading to a welcoming entrance of the house, surrounded by green grass.
Home in Fox Lake
4.88 out of 5 average rating, 26 reviews

Captain's Quarters 2/2 Lake Life Home with Hot Tub

Welcome to the Captain's Quarters Lake House, where breathtaking lake views and unparalleled charm await you on the stunning Chain O’ Lakes in Fox Lake! This unique 2 bedroom, 2 bathroom retreat is designed to offer you the ultimate lake house experience. As you step inside, you'll be greeted by a cozy yet spacious interior adorned with nautical decor, evoking the ambiance of a true captain's hideaway. For those who love to entertain, the full bonus bar is sure to be a highlight of your stay.

Guest favourite
A well-defined stone pathway leads to the entrance of the prairie-style home, bordered by lush green grass and neatly trimmed hedges. Hanging flower baskets add vibrant touches above the cozy seating area, surrounded by the serene backdrop of towering oak trees.
Guest suite in Riverwoods
4.95 out of 5 average rating, 441 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.

Top guest favourite
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.
Guest house in McHenry
4.96 out of 5 average rating, 198 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
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, 176 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!

Top guest favourite
The image presents a well-maintained yard leading to Fox Lake, with a clear view of the water. A pathway lined with flowers connects the house to the lakefront. The deck is visible, offering outdoor seating options, while the tranquil water reflects the sky above.
Home in Fox Lake
4.97 out of 5 average rating, 137 reviews

Enjoy Life Right on the Lake with Amazing Views

Welcome all Chain O'Lakes boaters and waterfront seekers to the resort style living that Fox Lake has to offer! Located directly on Fox Lake, enjoy breakfast on your beautiful deck, coffee, or wine on the balcony, then a day on the water. This stunning, meticulously maintained 1850+ square feet lakefront home was completely renovated in 2020. Have dinner on the deck with a view of the lake and the make your s’mores in the fire pit all while being on the edge of Mineola Bay.

Top guest favourite
The exterior of a modern single-story home is presented, featuring a manicured lawn and a paved driveway. Flanking the front, a welcoming porch with seating is visible. The light-colored building is complemented by a contrasting yellow side. Nearby, trees provide greenery and shade.
Home in McHenry
5 out of 5 average rating, 34 reviews

One-Level 3BR/2BA Fire Pit, All King Beds, Modern

Unwind in this peaceful, centrally located 3-bedroom, 2-bath home—all on one easy-access floor. Tucked in a quiet neighborhood just 2 minutes from Route 31 & IL-120, this home is your perfect hotel alternative. Enjoy king-size beds in every bedroom, a fully stocked modern kitchen, and a cozy living room with four recliners and Smart TVs in every room. Step outside to relax by the fire pit, enjoy dinner on the patio, or sip your morning coffee from the front porch rockers.

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
4.89 out of 5 average rating, 18 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).

Superhost
An open kitchen area is showcased with a wooden dining table and two white chairs. Modern appliances, including a microwave and a decorative wall with floral wallpaper, add a touch of charm. An oversized clock hangs above, contributing to the inviting ambiance.
Apartment in Lake Geneva
4.91 out of 5 average rating, 106 reviews

LG Quaint Condo on Lakeshore Dr.

Charming 1+1 condo off Lakeshore Blvd, just minutes from downtown Lake Geneva. A perfect blend of quaint and modern, with a full coffee and tea station and a fully equipped kitchen. Stroll to the lake, take a boat ride, or enjoy a scenic drive to downtown. Experience the peaceful charm of Lake Geneva with the convenience of being close to all its attractions. Book this condo alone or with another in the same building for extra space.

Popular amenities for Pistakee Highlands holiday rentals