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 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

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.

4.98 out of 5 average rating, 131 reviews

The exterior of the log cabin is illuminated against a night sky, highlighting the expansive wall of windows. A spacious deck is visible, framed by surrounding trees and a fenced yard, creating a cozy and inviting setting.

Cabin in Castle Manor

A Frame Log Cabin Near Multiple Local Lakes

Experience the allure of Salem Lakes Chalet, featuring modern comforts nestled within a quaint 3-story log cabin. Relax in a fenced yard offering picturesque vistas of woods, and relish in the variety of recreational options at nearby lakes. Your ideal retreat beckons! Enjoy the northern ambiance without the lengthy journey—be amazed by our expansive wall of windows! Whether you are in town to visit family or looking for a retrieve from the city we are conveniently located 10 mins from I-94.

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, 178 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 spacious living room features a stone fireplace with a large flat-screen TV mounted above. Comfortable leather sofas are arranged around a wooden coffee table, creating an inviting seating area. Large windows offer views of the lake, while a small decorative chair adds charm.

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, 126 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.

4.97 out of 5 average rating, 156 reviews

Condo in Lake Geneva

Magnificent waterfront views & cozy fireplace

Welcome to this serene waterfront villa in Lake Geneva, Wisconsin, a haven for relaxation. This elegantly designed one-bedroom retreat is perfectly nestled on the shores of Lake Como, offering a blend of rustic charm and modern comfort. The real brick walls and cozy fireplace create a warm and inviting atmosphere, providing unforgettable memories in this beautiful Wisconsin setting. Local laws require all guests names and address be provided prior to check in.

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!

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Other great vacation rentals in Pistakee Highlands

5 out of 5 average rating, 8 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

EmilyRating, 5 stars1 week ago

We loved staying in their home! It was the perfect place to get away from the city. It was a beautiful and short drive to Lake Geneva where we spent most of our time at. We also got the chance to stay in some of the days we were there and got the chance to cook in their grill. Their home is very cozy, clean, and quiet. We look forward to visit again soon!

5 out of 5 average rating, 22 reviews

A screened-in porch features a seating arrangement with plush chairs and a central table. Natural light streams through the screens, offering views of the serene lake and surrounding landscape. A ceiling fan hangs above, providing a comfortable breeze in the inviting space.

Home in Castle Manor

2BR Lake House | Lake Toys | Views | Dog Friendly

MagenRating, 5 stars1 week ago

We had the pleasure of staying here over our anniversary weekend with our 2 kiddos; it was our first vacation just our little family and it's was fantastic. Cristle was so helpful and went above and beyond to help us out when we had some issues on our end leading up to our trip. She was very thoughtful and kind and that alone was worth the 5 star rating. The home was very well kept and clean and had everything we needed for a nice relaxing weekend. We had a lot of fun out on the paddle boat and playing in the yard. The screened in porch was also a nice bonus. Our girls enjoyed the park and playing the sand. Overall it was a very nice stay and we'd love to go back sometime soon.

A stackable washer and dryer unit is positioned against a wall, offering practical laundry solutions in the utility room. The controls are clearly labeled, and the unit is enclosed in a clean, uncluttered space.

4.76 out of 5 average rating, 181 reviews

Enjoy Year Round Vacation On Pistakee Lake

LeahRating, 5 stars2 weeks ago

Our family enjoyed a short memorial day weekend! Had everything we needed, host we easy to communicate with, and loved the location!

4.92 out of 5 average rating, 24 reviews

A log-sided home is set against a clear blue sky, overlooking a heated pool. Lush greenery surrounds the pool area and a spacious deck features seating and umbrellas. The house showcases large windows and a balcony that opens to the serene landscape.

Villa in McHenry

Fabulous Cabin

ElaineRating, 5 stars4 days ago

Beautiful property! Phenomenally maintained and super clean! Kitchen and home were so well stocked! Great home!

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.

4.94 out of 5 average rating, 181 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

KrisRating, 5 stars1 week ago

Our Glass Cabin stay was absolutely perfect! It was beautiful and peaceful inside and out, a destination in itself. All communication was clear and questions were answered practically instantly. If you get an opportunity to stay here, you will consider yourself lucky when you leave!