Historic Route 66 Holiday Rentals

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Holiday Rentals in Historic Route 66

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (416)
"Great location for museum campus area!!!"
The price is NZ$407
includes taxes & fees
16 Jun - 17 Jun
Sentral Michigan Avenue
Sonder Market Hall
3.5 star property
8.4 out of 10, Very good, (88)
"Really pleased with my stay at the Market Hall. The process was extremely easy to reserve and access the room. The room was better than expected. I would definitely stay here again. Thanks Sonder!! "
The price is NZ$260
includes taxes & fees
16 Jun - 17 Jun
Sonder Market Hall
Sonder South Wabash
3.5 star property
8.8 out of 10, Excellent, (302)
"Everything was great!"
The price is NZ$370
includes taxes & fees
4 Jun - 5 Jun
Sonder South Wabash
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Kasa Magnificent Mile Chicago
4.0 star property
9.2 out of 10, Wonderful, (243)
"Clean, friendly, spacious and at an excellent location."
Kasa Magnificent Mile Chicago
Junipine Resort
3.5 star property
9.2 out of 10, Wonderful, (1799)
"What a beautiful duplex! We stayed in a creek side apartment and the view from the balcony was breathtaking! Would definitely recommend!!"
The price is NZ$376
includes taxes & fees
5 Jun - 6 Jun
Junipine Resort
Level Chicago – Old Town
4.0 star property
8.8 out of 10, Excellent, (209)
"Nice"
The price is NZ$769
includes taxes & fees
4 Jun - 5 Jun
Level Chicago – Old Town
Grand Canyon RV Glamping
1.5 star property
9.0 out of 10, Wonderful, (429)
"Overall great experience! Just wish if the hot water in the shower could run for more than 10 minutes each time."
The price is NZ$247
includes taxes & fees
2 Jun - 3 Jun
Grand Canyon RV Glamping
Found Chicago powered by Sonder
3.5 star property
7.6 out of 10, Good, (130)
"I enjoyed the fact that everything was close. The hotel was cleaned but I never saw a personal member. The code to enter didn't work and people inside had to help fellow clients to enter."
The price is NZ$357
includes taxes & fees
27 Jun - 28 Jun
Found Chicago powered by Sonder
Sonder The Burnham
3.5 star property
9.0 out of 10, Wonderful, (64)
" Cozy "
The price is NZ$452
includes taxes & fees
12 Jun - 13 Jun
Sonder The Burnham
The Neighborhood Hotel-Little Italy
2.0 star property
10.0 out of 10, Exceptional, (33)
"Great property, very clean, staff was only a message away and very friendly. Definitely recommend and would stay again. "
The Neighborhood Hotel-Little Italy
The St. Charles Guest House, lovely historic home, fun for families and groups
10.0 out of 10, Exceptional, (107)
"This house was perfect for our family to hang out and hit Main Street in St. Charles. The house itself has an updated kitchen and bathrooms and has enough space for a big family chill and watch movies or play video games. It is within walking distance of all the attractions on Main Street and if you are up to it, the Ameristar casino."
The St. Charles Guest House, lovely historic home, fun for families and groups
Village Camp Flagstaff
2.0 star property
9.4 out of 10, Exceptional, (56)
"Still building and working around the property. Seems like they are still working on finding staff and getting organized. On a Sunday afternoon, they ran out of pool towels. "
Village Camp Flagstaff
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (67)
"The building was clean and attractive. Security on site. Breakfast options close by. All the best sites walking distance. Units was amazing. Kasa very engaged and accessible. River Walk, boat excursions etc. Tours etc. Right there. Rooftop pool and all amenities on site wow!"
Kasa River North Chicago
1830's Luxury Brick Cottage, Cozy Fireplace, right off the Cobblestone Streets!
10.0 out of 10, Exceptional, (184)
"The cottage is immaculately furnished inside, and the bed is very comfortable. Just a very short walk to Main Street. Would recommend to anyone who is visiting St. Charles."
1830's Luxury Brick Cottage, Cozy Fireplace, right off the Cobblestone Streets!
Sonder Jewelers Row
3.5 star property
8.2 out of 10, Very good, (103)
"Loved it "
The price is NZ$463
includes taxes & fees
18 Jun - 19 Jun
Sonder Jewelers Row
WoodSpring Suites Chicago Addison
2.5 star property
6.0 out of 10, (184)
"Very nice property "
The price is NZ$155
includes taxes & fees
4 Jun - 5 Jun
WoodSpring Suites Chicago Addison
Fort Marcy Hotel Suites by All Seasons Resort Lodging
3.0 star property
8.8 out of 10, Excellent, (2122)
"The unit was right across the street from the White Cross of the Martyrs monument and the trail from there down to town below. The view from the unit was spectacular! The unit itself was okay - fine for our needs and what we wanted in a unit, but nevertheless is a bit run down - water stains on a wall, average facilities, construction next door. "
The price is NZ$421
includes taxes & fees
30 May - 31 May
Fort Marcy Hotel Suites by All Seasons Resort Lodging
White House at Grand Central
3.0 star property
9.0 out of 10, Wonderful, (71)
"Great and stay nice and quiet, clean comfortable will book again soon"
The price is NZ$328
includes taxes & fees
30 May - 31 May
White House at Grand Central
Arbor Suites at the Mall
2.0 star property
7.4 out of 10, Good, (2120)
"This was an amazing property!! So clean and fresh and it felt like a being in an apartment. It sleeps at least 4 adults 2 kids. (We had the two king beds and the pullout couch) plus it had a full sized refrigerator and a stove and dishwasher!! Separate bathrooms between the upstairs bedroom and the downstairs bedroom made it nice too. Plus the blackout curtains were great!! 10/10!!!"
The price is NZ$173
includes taxes & fees
30 May - 31 May
Arbor Suites at the Mall
Historic, Renovated Fire Station Vacation Rental!
3.5 star property
Historic, Renovated Fire Station Vacation Rental!
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See all available properties in Historic Route 66
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Historic Route 66 you may be interested in

Club Quarters Hotel, Central Loop, Chicago
4.0 star property
8.6 out of 10, Excellent, (3063)
"Great"
The price is NZ$309
includes taxes & fees
16 Jun - 17 Jun
Club Quarters Hotel, Central Loop, Chicago
Central Loop Hotel
4.0 star property
8.6 out of 10, Excellent, (1616)
"Nice restaurant downstairs, great location, safe and walkable. Rooms are on the smaller side but clean with nice staff. The only issue is the room temperature for an older hotel, warmer then was comfortable. Wifi was good."
The price is NZ$308
includes taxes & fees
16 Jun - 17 Jun
Central Loop Hotel
The Aquarius Casino Resort, BW Premier Collection
3.5 star property
8.0 out of 10, Very good, (5867)
"Rooms where together as requested, thank you"
The price is NZ$128
includes taxes & fees
30 May - 31 May
The Aquarius Casino Resort, BW Premier Collection
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Historic Route 66 holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Historic Route 66. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Historic Route 66. Seeing all the best attractions is bound to make you fall in love with Historic Route 66. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Historic Route 66 short-term rentals, that won’t be hard to do.

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