Vacation rentals in Pistakee Highlands

5 out of 5 average rating, 128 reviews

An inviting outdoor space is illuminated by string lights, creating a cozy atmosphere. A large dining table is surrounded by comfortable chairs, with colorful cushions adding a pop of color. Lush foliage and a fenced yard provide a private setting for relaxation.

Apartment in McHenry

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.

4.85 out of 5 average rating, 48 reviews

A gazebo is positioned near the water's edge, featuring a spacious dining table surrounded by several chairs. Lush green grass and scattered trees provide a natural backdrop, while the calming lakeview is visible in the distance. Paved stones create a clear path around the area.

Cabin in Spring Grove

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.

4.94 out of 5 average rating, 17 reviews

A wooden patio dining set is arranged around a rectangular table, surrounded by several matching chairs. In the background, lush greenery and a dock enhance the serene outdoor environment, with direct access to the calm waters.

Home in McHenry

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.

4.92 out of 5 average rating, 114 reviews

The exterior of the cozy cottage is highlighted by a blue facade, featuring a charming bay window with a small table and chair set in front. Lush greenery and garden beds add vibrancy to the entrance, creating a welcoming environment.

Cottage in Fox Lake

Cozy Cottage with Bedroom Lake Views!

Located on a hilltop peninsula overlooking Fox and Nippersink Lakes, Cozy Cottage is a 630 sq ft, 2 bed / 1 bath recently updated home with a large backyard — perfect for relaxing. You'll be conveniently located a 5 minute walk from waterfront bars and restaurants and have close driving proximity to: Downtown Fox Lake / Metra Station - 5 min Lake Geneva - 30 min Six Flags Great America - 30 min Illinois Beach State Park - 40 min Want to stay in? Our high speed wifi has you covered.

4.96 out of 5 average rating, 180 reviews

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

"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.

4.9 out of 5 average rating, 146 reviews

Home in Ingleside

Gorgeous Nautical 2/2 Lake House Chain O' Lakes

Unique and cute 2 bed / 2 bath nautical lake house has the best views of the Chain O' Lakes. Be amazed on the walk out lake view wood deck in the back yard, and watch sunsets fall over the bay and color the sky. The back patio is a great place to relax, entertain & relax. Fish or dock your watercraft at our pier if needed. There is an optional 5-6 person hot tub on the back deck for you to relax and unwind (See access and maintenance fee). Fully remodeled modern lake house

A cozy fire pit is surrounded by natural stone, with flames dancing brightly. Sticks hold marshmallows over the fire, while a tray of additional marshmallows sits nearby. A lake can be seen in the background, creating a calm and inviting atmosphere.

4.88 out of 5 average rating, 128 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!

4.99 out of 5 average rating, 150 reviews

A cozy seating area features a gray sofa and a small table with decorative items. Natural wood walls add warmth, while large sliding glass doors frame the serene lake view, leading to an outdoor deck overlooking the water.

Home in Round Lake Beach

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!

An open kitchen and dining area is featured, showcasing a large island with seating and sleek appliances. The space is illuminated by natural light streaming through large windows, with views of the lake visible in the background, enhancing the inviting environment.

4.97 out of 5 average rating, 127 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.

4.81 out of 5 average rating, 67 reviews

Two goats stand close to a fence in a pen, one white with brown markings and the other black and white. The surrounding area features straw and other goats seen in the background, enclosed by wooden fencing.

Farm stay in Lake Villa

Bunk House at Susanna Farms

Within an hour of Chicago, you and your family can enjoy country life on this beautiful small farm. Surrounded by forest preserves on a quiet road so you feel like you're out in the country while still close to lots of stores and amenities. Say hello to the horses, chickens, goats, and sheep. Have a bonfire to roast marshmallows outside or enjoy cozy seating or large dining table in the great room. Full kitchen. Large living space and bedroom.

4.83 out of 5 average rating, 101 reviews

A sandy beach area is surrounded by green grass and features a shallow swimming area. Several individuals are enjoying the water, while others are seated under blue umbrellas on a deck. A large building with a covered patio overlooks the beach.

Cottage in Antioch

#4: Cute 2 bedroom cottage on the beach!

Come relax at Turtle Beach Marina! Rent a Pontoon, Kayak, or even a Wave Runner. Spend the day at the beach and at the beach bar (Beach bar is open Thursday through Sunday until the first weekend in October). Quaint cottage has 2 bedrooms with a full bed in each. Up to 4 people allowed. There is no oven but has a 2 burner electric cook top. A grill is also available. Beach themed cottage is completely remodeled. 💜

4.85 out of 5 average rating, 71 reviews

A long, silver-colored dock extends over calm water, leading towards the horizon. A clear blue sky with wispy clouds is visible above, and the shoreline features a mix of greenery and distant buildings, enhancing the lakeside setting.

Cabin in Pistakee Lake

Cozy Brick House Chain O'Lakes

Welcome to our cozy Tiny Brick House on Chain O'Lakes in Fox Lake! Newly remodeled, this fully furnished house offers a queen-sized bed, sleeper couch, modern kitchen & (tiny) bathroom. With water front access to Chain O'Lakes & stunning views, it's perfect for fishing, boating, or relaxing. Just a short walk to train station, restaurants, shops & local attractions. Book now for a memorable getaway!

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Pistakee Highlands vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Pistakee Highlands

5 out of 5 average rating, 9 reviews

A dining area features a wooden table surrounded by four wicker chairs. Natural light illuminates the space through multiple windows. Wooden beams create texture on the ceiling, complemented by a woven pendant light above the table. Soft furnishings can be seen in the adjoining living area.

Home in Twin Lakes

Cozy Cabin in Town | Walk to Lake Mary

DavidRating, 5 starstoday

We had a great stay. The house was perfect for a quick weekend getaway. We enjoyed some of the local spots in Twin Lakes and made the short drive for dinner in Lake Geneva. Highly recommend!

The outdoor area features a spacious lawn with lush greenery, framed by tall trees. A patio with stone flooring is visible in the foreground, overlooking a garden with various plants. A children's play set is positioned toward the right side, contributing to the family-friendly setting.

Guest suite in McHenry

4.82 out of 5 average rating, 82 reviews

Private in-law apt. on the Popular Chain of Lakes!

RenaRating, 5 stars66 months ago

We had a wonderful weekend in McHenry at Greg's place. It is unique, comfortable, spacious, and pretty close to a main downtown area with lots of restaurants/bars. The window views are beautiful. And, we especially loved the sauna and fireplace! We stayed in the winter and didn't get to fully enjoy the lake and large yard, so we will definitely have to come back in the summer.

4.94 out of 5 average rating, 50 reviews

A wooden dock extends into the calm waters of Lake Pistakee, surrounded by a serene landscape. Soft clouds drift across the blue sky, reflecting on the water's surface. The area appears tranquil, inviting relaxation and connection with nature.

Cottage in McHenry

Lakefront Views, Free Water Sports!!

LarryRating, 5 stars2 weeks ago

Very great get away I’m a fisherman and caught some really big fish. Water was clean lots to do on the chain of lakes. Only 9 mins from McDonald’s and Walmart in case anyone needs last minute stuff. Chris and Shannon were very knowledgeable of the area. Great place for peace. Sunset is on bedroom window side. (Loved to see this as I was just getting up) neighbors were friendly. Love the fact we had water toys like paddle boat kayaks and paddle board for use even though I didn’t use them I was fishing my 3 days there. There’s a dock and water at dock is about 2’-3’. Would highly recommended them. Overall it was a great stay and will be coming back again. To all who is looking at this you will love this environment. I consider this place a happy place getaway. Caught cat fish, drum,bass,,walleye Maybe rent a boat and explore the chain of lakes next time. Thank you Shannon and Chris for the great experience

The kitchen features a spacious island topped with granite, surrounded by cushioned stools. Large windows fill the area with natural light, showcasing a welcoming seating nook beside the entrance. Cabinets provide ample storage, complementing the overall modern design.

4.77 out of 5 average rating, 113 reviews

This is a VACATION spot! With a million dollar view! bring your water toys, or just float right off the pier, for wonderful swimming!

ChristianRating, 5 stars1 month ago

Great place to stay, amazing view of the lake with a huge window. It was a great time and a nice spot for a getaway! Nice outdoor deck too.

4.95 out of 5 average rating, 182 reviews

A serene indoor space is showcased, featuring a large table surrounded by floor cushions in calming hues. Natural light filters through expansive windows, revealing a snow-covered landscape and a tranquil water view beyond. An elegant plant adds a touch of greenery to the setting.

Home in Richmond

TheGlassCabin@HackmatackRetreat

JayRating, 5 starstoday

What a beautiful rustic setting. So many wonderful Buddhist / mindfulness reminders to disconnect and slow down. We would love to come back to this getaway location again!

Cottage in Fox Lake

4.82 out of 5 average rating, 168 reviews

All Season Sunset Cottage on Pistakee Lake

ReneeRating, 5 stars2 months ago

Beautiful waterfront property and cozy cottage. The house is minutes from the train station so you can plan a trip to the city without the traffic. The lake is full of pelicans, ducks and geese and I never tired of watching them. The driveway is an absolute adventure! We took turns riding in the back and front of our rental mini van so we could all experience the incline. You’ll be fine-just do it-it’s fun! The neighborhood and surrounding areas are beautiful and there’s plenty of restaurants and shopping nearby. There is limited cabinet and refrigerator space so don’t over buy groceries like we did and there’s no ice. Bring trays or buy a bag if you need this. The fire pit was used and we got firewood at Home-depot along with s’mores sticks. The house is stocked with everything needed and we had an amazing time and made unforgettable memories and were comfortable and surrounded by beautiful scenery.

5 out of 5 average rating, 12 reviews

A white wooden chair is positioned on a deck overlooking the water, framed by a large tree. The scene captures a serene atmosphere, with sunlight reflecting off the water's surface and a glimpse of neighboring properties in the distance.

Cottage in Fox Lake

Lakefront Cottage with Gorgeous Sunsets

HillaryRating, 5 stars3 weeks ago

Josh is a great host, very responsive. The lakehouse is a cute weekend getaway. The sunsets are gorgeous and the house is cozy and heats up well (we stayed when it was chilly outside).

A spacious living area is presented, featuring large windows that frame scenic lake views. A cozy sectional couch and coffee table are arranged nearby the fireplace. The space is illuminated by natural light, with a ceiling fan creating a comfortable atmosphere.