Vacation rentals with a pool in Dundee Township

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Top-rated rentals with a pool in Dundee Township

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Guest favorite

Apartment in Chicago

4.89 out of 5 average rating, 463 reviews

Whole Flat in Private Club. Walk to L, Dining & Shows

Find unrivaled amenities in the newly restored Lawrence House, a Deco gem lauded a “unique architectural treasure” by the Chicago Architecture Foundation. Bask in an over-sized double lounger on the roof-top deck with 360-degree skyline views. Detox in the state-of-the-art fitness center with boxing gym. Soak in the 50-foot mosaic-tiled pool. Come home to a sunny, open-layout flat, with a cozy private bedroom, spa-like bathroom, fully-equipped kitchen, and free washer/dryer. Work or play in the terrazzo-floored Grand Lobby with club seating, adjoining cafe, craft cocktail bar and restaurant. Newly restored, sunny and spacious, immaculate, hotel-styled one-bedroom apartment with all new fixtures and appliances. Cozy bedroom with comfortable queen bed, flat screen TV, and large closet. Living room with couch that pulls out to a full-sized bed, club chair, large flat screen TV, and drop-leaf table for working. Stocked kitchen with everything you need to cook full meals, a new Smeg fridge, granite counters, and bar-stool seating. A queen-sized Serta air mattress allows up to 5 people to sleep comfortably. Central heat and air conditioning. Free washer/dryer in unit. Just-restored Art Deco building, called a "unique architectural treasure" by the Chicago Architecture Foundation. Unrivaled, private-club styled amenities. State of the art fitness center. Mosaic-tiled 50-foot pool. Roof-top lounge and deck with 360-degree skyline views, and tons of over-sized double loungers. Garden patio with fire pit, grills and picnic tables. Grand Lobby with cafe and craft cocktail bar, club seating, striking stained-glass skylight, ornate plaster moldings and terrazzo floor. Privacy guaranteed. The entire apartment is yours. You may also use the building's gorgeous amenities: fitness center, pool, roof-top lounge and deck, and garden patio. We have a self check-in and check-out system to provide you the most flexibility. However, we are always available to answer any questions, address any concerns, and provide recommendations. In the heart of Chicago's premier live-music and entertainment district, steps from two major concert venues and a legendary jazz lounge. Walk to dozens of restaurants and bars. Two blocks to the Beach. One block to the Red Line 'L' train, which goes straight to Wrigley Field in 5 minutes, and the Loop in 20 minutes. To learn more about the area, check out the Chicago Sun-Times feature on Uptown by googling: “sun times uptown neighborhood” One block to Red Line 'L' station. Free street parking with permits provided. Pets may live in the building but there are no pets allowed in this unit. In the heart of Chicago's premier live-music and entertainment district, steps from two major concert venues and a legendary jazz lounge. Walk to dozens of restaurants and bars. Two blocks to the Beach. One block to the Red Line 'L' train [temporarily 3 blocks while my station is rebuilt], which goes straight to Wrigley Field in 5 minutes, and the Loop in 20 minutes. To learn more about the area, check out the Chicago Sun-Times feature on Uptown by googling: “sun times uptown neighborhood guide”

Nov 30 – Dec 7

G$87,137 GYD per night

Guest favorite

Guest suite in Bartlett

4.96 out of 5 average rating, 185 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.

Sep 18 – 25

G$22,786 GYD per night

Guest favorite

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.

Oct 19 – 26

G$19,330 GYD per night

Guest favorite

Condo 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.

Sep 24 – Oct 1

G$33,389 GYD per night

Guest favorite

Condo in Lisle

4.95 out of 5 average rating, 42 reviews

Peaceful Condo in Lisle, Illinois

Quiet condo with balcony overlocking the forest located in Lisle. Minutes from I-88, I-355, Commuter train goes directly to Chicago, Benedictine University , North Central College , Wheaton College. Shopping, movie, restaurant are walking distance. Access to pool , Lake , fishing, disc golf, canoes, tennis court, volleyball, walking paths, ski and snowboard hill, Restaurant/ pub with live music and entertainment, Convenience store. Discounts for weekly bookings longer stays over 28 days.

Jan 28 – Feb 4

G$16,489 GYD per night

Guest favorite

Apartment in Chicago

4.87 out of 5 average rating, 156 reviews

Stunning Panoramic Chicago Views & Free Parking

Indulge in the epitome of luxury at our exceptional property with a host of amenities: 24-hour door attendant, heated parking, hot tub, modern workout and rec room, and stunning Chicago views. Situated in a secure, scenic South Loop neighborhood, our upscale abode grants swift access/steps to McCormick Place and Wintrust Arena. Discover the best of Chicago from this ideal spot, with easy public transport and airport commutes. Your remarkable experience begins in this lavish urban retreat!

Nov 1 – 8

G$84,375 GYD 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.

Oct 26 – Nov 2

G$56,710 GYD per night

Guest favorite

Condo 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.

Jul 28 – Aug 4

G$53,948 GYD per night

Guest favorite

Condo 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.

Apr 7 – 14

G$22,895 GYD per night

Guest favorite

Condo in Lake Geneva

4.93 out of 5 average rating, 428 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!

Sep 25 – Oct 2

G$27,879 GYD per night

Guest favorite

Condo 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!

Dec 12 – 19

G$29,555 GYD per night

Superhost

Cabin in Union

4.86 out of 5 average rating, 7 reviews

Pet friendly Rustic Cabin

You won’t forget the delightful surroundings of this rustic (no bathroom) cabin. It is designed for guests, that like to bring their dog camping! There is a fenced-in area, that includes a large brick fire ring and one of our popular patio swings! The cabin is equipped with an a/c unit (or space heater when necessary), small refrigerator and parking space for one car. Bathrooms and showers are located in the nearby main building.

Dec 18 – 23

G$20,536 GYD per night