Vacation rentals in Pistakee Highlands

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Top-rated vacation rentals in Pistakee Highlands

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Guest favorite

Cottage in Lake Villa

4.82 out of 5 average rating, 150 reviews

Laura’s Little Cottage

First, I’d like to mention this is located in a QUIET neighborhood. I don't rent out for big, loud parties. If that's what you're looking for, this is not the place for you. I like to keep peace with the neighbors! Moving on. This little cottage is just minutes from several forest preserves, the Chain O’ Lakes, Great America or Wilmot Mountain. 30 minutes to Great Lakes Naval Base & less than an hour to Lake Geneva, Chicago or Milwaukee. Plenty of restaurants, & grocery stores. 30 day minimum

Dec 30 – Jan 6

G$30,636 GYD per night

Superhost

Home in Fox Lake

4.9 out of 5 average rating, 128 reviews

Charming Lake Cottage ★ Queen Bed ★ Chain O Lakes

Outdoor enthusiasts will be delighted with this romantic 1 bedroom lake cottage that sleeps 4. The fall colors, hiking, and nature setting is especially breathtaking this time of year. Walk down to the lake to enjoy boating, swimming, fishing, and more. Experience all the comforts of home in this newly remodeled cottage desirably located on Lippincott Point. Perfect for romantic getaways, gathering with friends by the lakeside fire pit, boating “the chain” and all that lake life has to offer!

Dec 10 – 17

G$31,182 GYD per night

Guest favorite

Cabin in Spring Grove

4.9 out of 5 average rating, 20 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. A lovely space to unwind and relax by the lake whether it is work or play. Awake refreshed 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.

Jun 15 – 22

G$27,084 GYD per night

Guest favorite

Home in Harvard

4.95 out of 5 average rating, 164 reviews

Sanctuary Woodland Guest House!

Our guest house is located on a picturesque 5 acres, next to a woodland forest. We also run a bird sanctuary on the property, Georgia's Place Bird Sanctuary, which makes this a paradise for an animal lover! We are happy to give guests a tour of our sanctuary. There is a large deck and fire pit for an enjoyable evening, and a walking trail for wildlife enthusiasts! We kindly ask guests not to bring meat onto the property as we are running a sanctuary that promotes compassion for all animals.

May 5 – 12

G$25,025 GYD per night

Guest favorite

Cottage in Fox Lake

4.92 out of 5 average rating, 89 reviews

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.

May 9 – 16

G$26,459 GYD per night

Guest favorite

Guesthouse in McHenry

4.95 out of 5 average rating, 155 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.

Dec 12 – 19

G$28,486 GYD per night

Guest favorite

Home in Ingleside

4.93 out of 5 average rating, 110 reviews

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

Dec 5 – 12

G$42,319 GYD per night

Guest favorite

Home in Round Lake Beach

4.89 out of 5 average rating, 148 reviews

Corner Lakefront Property

This unique place has a style all its own. This corner lake house comes with a huge fenced-in yard, as well as a balcony off of the master bedroom and 2 parking spots. We offer 3 kayaks with life jackets, 1 paddle board, paddle boat and fishing poles, fire pit, outdoor and indoor games. We have 3 bedrooms with beds included, as well as a futon couch a trundle bed and a pull-out couch bed (6 potential beds total). This comes with 2 TVs, fireplace, WiFi, bar, new fridge and more.

Dec 1 – 8

G$48,803 GYD per night

Guest favorite

Guest suite in Zion

4.9 out of 5 average rating, 135 reviews

Non-smoking, attached mother-in-law suite.

30 minutes away from the Naval Station 5 minutes away from the beach. 10 minutes to Wisconsin. 1 hour to O’Hare Airport and downtown Chicago. 1 hour to Milwaukee 25 minutes to Six Flags and Great Wolf Lodge. Safe and quiet neighborhood with plenty of wildlife right in the back yard. This Mother in Law suite has tons of natural light. For nature lover’s this unit is close to the beach and there are walking trails nearby. Small children maybe heard from 7AM to 7PM.

May 5 – 12

G$16,777 GYD per night

Superhost

Cabin in Fox Lake

4.88 out of 5 average rating, 40 reviews

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! PLEASE NOTE: laundry area is shared in the detached basement!

Nov 9 – 16

G$32,213 GYD per night

Guest favorite

Cottage in McHenry

4.93 out of 5 average rating, 46 reviews

Lakefront Views, Free Water Sports!!

Relax at this stunning lake house on Lake Pistakee. Enjoy this cozy house with a private lakefront view on a sleepy dead end street. This lake house underwent a full rehab in 2019. House features its own private dock right on the water and includes 2 free kayaks, 2 free paddle boards, and a free paddle boat to use. Enjoy the fire pit overlooking the water and free gas grill (byow). Lake Pistakee is on the Chain o Lakes which includes 14 connected lakes

Nov 7 – 14

G$78,399 GYD per night

Guest favorite

Cottage in Fox Lake

4.94 out of 5 average rating, 111 reviews

Waterfront Cottage in the Heart of Fox Lake

Spend the weekend or a lengthy stay in the heart of Fox Lake. Enjoy our lakefront cottage with enough beds to sleep 6. Our home is the perfect getaway to enjoy everything from fishing & water sports, dining, nightlife or even snowmobiling and skiing in the winter. Or relax with family and friends at this peaceful place along the lake with beautiful views. Canoe available on site.

May 28 – Jun 4

G$38,747 GYD per night