Holiday rentals with a pool in McHenry County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in McHenry County

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite

Guest suite in Bartlett

4.96 out of 5 average rating, 186 reviews

Cozy & Spacious Suite in Quiet Neighborhood

This 950 sq. ft. guest suite is in a quiet, upscale neighborhood, less than 1/2 mile from Bartlett Hills Golf Club and a mile from Metra Train Station. 50 min. train ride to downtown Chicago. 10 min. walk to downtown Bartlett. A private entrance makes check-in easy and convenient, while offering privacy during your stay. Full kitchen, accessible bathroom, WIFI, and cable provided. Washer/Dryer available upon request. Pool is for registered guests only. Owners on site to assist if needed.

18–25 Dec

$150 SGD per night

Guest favourite

Apartment in Lake Geneva

4.98 out of 5 average rating, 174 reviews

Lake Geneva Cloud 9

A resort community with outdoor pool (open during the summer season only) boat launch, tennis courts and small craft rentals on the premises. Beautiful views of Lake Como from the patio. Five minute drive to Downtown Lake Geneva. Free parking and keypad entry. Walk to The Ridge Hotel Resort and enjoy the use of their amenities for a small user fee which includes indoor and outdoor pools, spa, whirlpool, fitness center and restaurant. The condo is comfy and ready to make your stay memorable.

26 Sep – 3 Oct

$220 SGD per night

Guest favourite

Guest suite in St. Charles

5.0 out of 5 average rating, 251 reviews

Peaceful Private Coach-House in St. Charles

Enjoy our cozy and peaceful Coach-house , private entrance with everything you need for a wonderful stay. Newly renovated and updated throughout. Queen bed, studio area includes blue ray player, reverse osmosis drinking water, Keurig coffee machine and quick-set lock. Even though you are less than a mile from downtown St. Charles and 4 miles to the Geneva train station you have a private area. You may see deer out your window overlooking the pool and tennis. Not suitable for children or pets.

16–23 Oct

$127 SGD per night

Superhost

Home in Milton

4.85 out of 5 average rating, 184 reviews

Tree Top House with mini indoor pool and sauna

Welcome to the tree top house. A great place to stay any time of year Situated in a wooded setting on 10.5 acres this beautifully hand crafted home offers a great outdoor environment and many amenities including a mini indoor heated pool, sauna, two fireplaces, cathedral wood ceiling great room and dining area, spacious deck and private fire pit. Four private bedrooms, two of which have fireplaces in them and all with beautiful wood views. Three nature paths are available for taking walks.

22–29 Apr

$254 SGD per night

Guest favourite

Home in Highland Park

4.9 out of 5 average rating, 125 reviews

2-Acre Highland Park Retreat with Heated Pool ~ 5*

Experience luxury of this award winning 6BR 4Bath family home in picturesque Northshore private estate. Spend day by the private heated pool, enjoy beauty of gardens, explore local landmarks, starting with the gates of neighborhood Michael Jordan estate. The stylish design and rich amenity list will leave you in awe. ✔ Two-Acre Estate ✔ 6 Comfy BRs ✔ Multiple Living Areas ✔ Full Kitchen ✔ Backyard (Pool, Lounges, BBQ) ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Free Parking See more below!

13–20 Mar

$1,566 SGD per night

Superhost

Chalet in Ingleside

4.84 out of 5 average rating, 369 reviews

"A" Frame Brandenburg Lake

Getaway to a cozy 1 bedroom w/loft for 2, up to 6 people. Full kitchen 1.5 bath all season getaway. There is a piano as well. A tranquil home steps from a private lake. Oak and Pine surround you plus a stone fireplace, it feels like the North Woods. The A Frame guest house shares a 5 acre compound ( total 20 Acres) with the owners residence and caretaker cottage. The Volo Bog 800ft away. No hot tub Nov - May. Swimming pool usually June-October often cool to use in early June.

7–14 Aug

$379 SGD per night

Guest favourite

Apartment in Lake Geneva

4.97 out of 5 average rating, 100 reviews

Minutes from DT Lake Geneva! Pool! Fireplace!

Your peaceful getaway begins in a newly remodeled, ground level condo with patio, conveniently located between Lake Como and Lake Geneva in Interlaken Resort! Just a short peaceful walk to lake, restaurants, pool, tennis, volleyball, boat launch, small craft rentals, and more! The resort community is located by The Ridge Hotel, which adds additional restaurants and available amenities at an additional charge. Many local areas to explore & visit will await your arrival.

19–26 Nov

$225 SGD per night

Guest favourite

Apartment in Lake Geneva

4.96 out of 5 average rating, 57 reviews

LG Quaint Condo on Lakeshore Dr. W/boat parking

Free Boat Parking 1+1 condo off Lakeshore Blvd, just minutes from downtown LG. Home is the perfect balance of quaint meets modern touch. Wake to a full coffee and tea station, cook in your own full kitchen. Walk to the lake, take a boat out just a few blocks away, or enjoy a scenic drive downtown. Experience the quiet and original charm of Lake Geneva without sacrificing the convenience of being close to DT LG. Book alone or with another condo in the same building.

20–27 Mar

$179 SGD per night

Guest favourite

Apartment in Lake Geneva

4.93 out of 5 average rating, 429 reviews

Charming, Cozy & Quaint Condo in Lake Geneva!

Quaint 1 BD 1 BA Condo by Lake Como. The association outdoor pool is newly remodeled. There is a boat launch and parking, paddle board rentals, and tennis court. The hotel next door has pools to use for a fee. Dine at the popular nearby Mars restaurant or check out the Ridge Hotel’s coffee shop, restaurant & huge outdoor fire pit! Condo offers towels, toiletries, games, WiFi, basic cable, Roku, electric grill, gas fireplace, drip & K-cup coffee, tea, & water!

18–25 Oct

$167 SGD per night

Guest favourite

Apartment in Lake Geneva

4.96 out of 5 average rating, 141 reviews

Relaxing Villa with Amazing Amenities!

Resort day passes included with booking! Hot tub, indoor and outdoor pool, outdoor bar and fire pit, sauna, the list goes on! Only five minutes from downtown Lake Geneva, this second floor condo offers the best of both worlds. Enjoy the laid back Lake Como attractions, or have a blast in Lake Geneva! This hidden gem is perfect from golfers (only 5 minutes from Geneva National) to families. Give us a try, and enjoy a discount on your second stay!

13–20 Sep

$215 SGD per night

Guest favourite

Farm stay in Lake Villa

4.86 out of 5 average rating, 50 reviews

Country Living Close to Town

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 ducks. Have a bonfire to roast marshmallows outside or enjoy a fire in the large living room. Full kitchen. Large living space and bedroom.

20–27 Dec

$165 SGD per night

Guest favourite

Home in Lake Geneva

4.91 out of 5 average rating, 126 reviews

Home away from Home

Looking for a fun, cozy and relaxing get away? This home is perfect for that! We have lots of amenities to enjoy. Heated in ground Pool, Beach towels, Sunroom, Game room and so much more! We are walking distance to Downtown lake Geneva attractions, Beach, Restaurants and Shopping! but far enough away in this quiet part of town. This house is well stocked for a great getaway and awesome memories!

26 Mar – 2 Apr

$773 SGD per night