Historic Route 66 Vacation Rentals

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Vacation Rentals in Historic Route 66

Bar (on property)
The St. Charles Guest House, lovely historic home, fun for families and groups
10.0 out of 10, Exceptional, (106)
"Had a wonderful weekend get away in St. Charlies. The house was so close to main street, but far enough away not to hear the noise. The house had everything and more! The water and snacks were a nice touch. Everything was very clean. Would stay here again."
The St. Charles Guest House, lovely historic home, fun for families and groups
Bar (on property)
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!
Property grounds
Escape to PARADISE on 10 sprawling acres in which to do anything you please!
10.0 out of 10, Exceptional, (4)
"Very nice attentive people, they were amazing host!! great place away from town with beautiful sunsets. 10/10!!"
The price is CA $433
CA $493 total
includes taxes & fees
May 26 - May 27
Escape to PARADISE on 10 sprawling acres in which to do anything you please!
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50-inch Smart TV with satellite channels
The Neighborhood Hotel-Little Italy
2.0 star property
9.8 out of 10, Exceptional, (30)
"Beautiful, spacious, clean rooms. Cozy safe neighborhood. Prompt and responsive communication. Would absolutely stay here again!!"
The Neighborhood Hotel-Little Italy
Mini-fridge, microwave, coffee/tea maker, toaster
Inn History Grand Canyon
3.0 star property
9.8 out of 10, Exceptional, (88)
"We only stayed one night on our travel from Grand Canyon to Phoenix but it would have been fun to stay longer. The unit is lovely with so many details to explore that we didn’t have time to take it all in. The attention to detail in the decor is amazing. We had three people so one adult slept on the sofa bed and said that it was very comfortable. The bed was also very comfortable and had nice pillows and linens. We booked through Expedia and had no contact from the hosts other than the...
The price is CA $210
CA $298 total
includes taxes & fees
Jun 10 - Jun 11
Inn History Grand Canyon
Exterior
Walking distance to restaurants, shops and Lake Michigan,
9.8 out of 10, Exceptional, (156)
"We stayed here for our daughter's graduation. It was a perfect home base for everything we needed to do. Ross was attentive and thorough in explaining everything we needed to know about the unit, garage parking was a plus, beds were comfortable...overall a great stay."
Walking distance to restaurants, shops and Lake Michigan,
Property grounds
Wrigley/Southport Corridor Garden Oasis +parking!
9.8 out of 10, Exceptional, (37)
"Convenient location. Clean, modern style. Everything was excellent!"
Wrigley/Southport Corridor Garden Oasis +parking!
Exterior
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (65)
"Very clean and comfortable. Great location very close to an L stop. Walkable to shopping and the lake front and river walk"
Kasa River North Chicago
Lobby sitting area
Village Camp Flagstaff
2.0 star property
9.4 out of 10, Exceptional, (53)
"We loved our tiny house cabin so much! It was adorable, comfy and in a great location! We’d come back again for sure!"
Village Camp Flagstaff
Family Apartment, 3 Bedrooms, Non Smoking, Balcony | Living area
Kasa South Loop Chicago
4.0 star property
9.4 out of 10, Exceptional, (161)
"Highly recommend! Amazing view of the city and the lake, clean and quiet yet close to everything. Thoughtfully furnished with nice surprises like power strips, white noise machine in bedroom, electric kettle etc. It was ideal and we’d stay there again. "
Kasa South Loop Chicago
Interior
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (404)
"The check in was flawless and got to an impecable room."
The price is CA $170
CA $240 total
includes taxes & fees
May 27 - May 28
Sentral Michigan Avenue
Terrace/patio
Junipine Resort
3.5 star property
9.2 out of 10, Wonderful, (1787)
"Loved this resort, our unit had a full kitchen to cook meals and the view from the patio was beautiful. Will definitely be staying here again with the family! "
The price is CA $338
CA $385 total
includes taxes & fees
Jun 3 - Jun 4
Junipine Resort
49-inch Smart TV with digital channels, TV, streaming services
Kasa Magnificent Mile Chicago
4.0 star property
9.2 out of 10, Wonderful, (224)
"Everything was great. From easy check in to easy check out. The room was very nice and cozy. Very clean. Amazing view of downtown from the bedroom and balcony. I will be staying here again! "
Kasa Magnificent Mile Chicago
Superior Loft | Private kitchen
Grand Canyon RV Glamping
1.5 star property
9.0 out of 10, Wonderful, (423)
"The front desk staff was friendly and informative. Provided extras and assured us if we had any issurs, that someone was onsite to help even after the office closed."
The price is CA $127
CA $238 total
includes taxes & fees
May 19 - May 20
Grand Canyon RV Glamping
Exterior
Sonder The Burnham
3.5 star property
9.0 out of 10, Wonderful, (56)
"Great set up and everything was easy. Short walk to Clinton/Blue line. Walls/floor/ceiling are indeed thin but if you’re prepared for that, it’s well worth it to have the two bedrooms and all of its conveniences. Would definitely stay in a Sonder again! "
The price is CA $270
CA $317 total
includes taxes & fees
May 29 - May 30
Sonder The Burnham
Comfort Apartment
White House at Grand Central
3.0 star property
9.0 out of 10, Wonderful, (70)
"Second time I’ve stayed and it was even better than the first! Had some bottles of wine and glasses out set out when I arrived! It’s the little things that matter! "
The price is CA $96
CA $275 total
includes taxes & fees
May 21 - May 22
White House at Grand Central
Private kitchen
Luxury Home Away From Your Home
9.0 out of 10, Wonderful, (106)
"The host communicated well. The area was busy but felt safe. I felt it was expensive for the location. Very clean."
Luxury Home Away From Your Home
Reception
Kasa Forest Park St. Louis
3.5 star property
9.0 out of 10, Wonderful, (98)
"The apartment was amazing! The outdoor patio near the club house was messy and i was nervous to use the hot tub. I was disappointed because i really wanted a use the outdoors space. But otherwise it was great! "
Kasa Forest Park St. Louis
City view from property
Sonder South Wabash
3.5 star property
8.8 out of 10, Excellent, (295)
"Overall the stay was amazing. We will definitely be booking here again."
The price is CA $276
CA $324 total
includes taxes & fees
Jun 9 - Jun 10
Sonder South Wabash
Front of property - evening/night
Level Chicago – Old Town
4.0 star property
8.8 out of 10, Excellent, (207)
"Nice"
The price is CA $276
CA $347 total
includes taxes & fees
May 27 - May 28
Level Chicago – Old Town
Don't see what you're looking for?
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

Exterior
Club Quarters Hotel, Central Loop, Chicago
4.0 star property
8.6 out of 10, Excellent, (3053)
"The hotel and staff are great. The beds are terrible, rooms need some maintenance "
The price is CA $206
CA $241 total
includes taxes & fees
May 27 - May 28
Club Quarters Hotel, Central Loop, Chicago
Exterior
Central Loop Hotel
4.0 star property
8.6 out of 10, Excellent, (1621)
"Very nice hotel for the price. The location is in the business district, close to the Art Institute. We had a suite, a large room. Very clean and very friendly staff."
The price is CA $186
CA $218 total
includes taxes & fees
May 28 - May 29
Central Loop Hotel
Front of property
Warwick Allerton - Chicago
4.0 star property
7.8 out of 10, Good, (2587)
"Large, super clean, convenient hotel. Staff was excellent and friedly. Bar staff was great. Would definitely stay again."
The price is CA $150
CA $196 total
includes taxes & fees
May 27 - May 28
Warwick Allerton - Chicago
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 vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

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