Historic Route 66 Holiday Rentals

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Holiday Rentals in Historic Route 66

Interior
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (411)
"The front desk staff were incredibly helpful, cheerfully assisted me with check-in and stored my extra bags early in the day when I went to work on the day u checked out. A service."
The price is HK$1,118
per night
27 May - 28 May
Sentral Michigan Avenue
Interior
Sonder Market Hall
3.5 star property
8.2 out of 10, Very good, (84)
"I loved having the whole space to ourselves. Felt the privacy of the entire building, more than a hotel. It was great. Would probably book again!"
The price is HK$801
per night
27 May - 28 May
Sonder Market Hall
City view from property
Sonder South Wabash
3.5 star property
8.8 out of 10, Excellent, (300)
"It was a pleasant stay"
The price is HK$1,516
per night
28 May - 29 May
Sonder South Wabash
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49-inch Smart TV with digital channels, TV, streaming services
Kasa Magnificent Mile Chicago
4.0 star property
9.2 out of 10, Wonderful, (238)
"Excellent location, studio, and support!"
Kasa Magnificent Mile Chicago
Terrace/patio
Junipine Resort
3.5 star property
9.2 out of 10, Wonderful, (1795)
"We tried for early check in but it was unavailable. Once checked in the unit was clean except the upstairs was musty smelling. The air conditioning systems was multiple split units which worked but we had to turn on an overall unit fan for them to work properly. The hot tub had a lose headrest. The restaurant closes early and for a very few tables had extremely slow service. Took 40 minutes to get our drinks. Overall I wouldn’t go back the stay for the price doesn’t align. "
The price is HK$1,758
per night
9 Jun - 10 Jun
Junipine Resort
Front of property – evening/night
Level Chicago – Old Town
4.0 star property
8.8 out of 10, Excellent, (208)
"Nice"
The price is HK$1,586
per night
27 May - 28 May
Level Chicago – Old Town
Private kitchen
Grand Canyon RV Glamping
1.5 star property
9.0 out of 10, Wonderful, (428)
"Great place to experience an RV or Camper lifestyle. Couldn’t do much because it ended up snowing but we were able to keep warm. The staff was friendly and attentive and it was an quick and easy check in. And it’s next to a truck stop with lots to offer. "
The price is HK$499
per night
30 May - 31 May
Grand Canyon RV Glamping
Interior
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 HK$1,445
per night
17 Jun - 18 Jun
Found Chicago powered by Sonder
Exterior
Sonder The Burnham
3.5 star property
9.0 out of 10, Wonderful, (62)
" Cozy "
The price is HK$1,516
per night
28 May - 29 May
Sonder The Burnham
50-inch Smart TV with satellite channels
The Neighborhood Hotel-Little Italy
2.0 star property
10.0 out of 10, Exceptional, (32)
"Great property, very clean, staff was only a message away and very friendly. Definitely recommend and would stay again. "
The Neighborhood Hotel-Little Italy
Bar (on property)
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
Lobby sitting area
Village Camp Flagstaff
2.0 star property
9.4 out of 10, Exceptional, (53)
"Nice little cozy cabin with lots of amenities. It was only 2 of us but it slept 6 for being small. It had all the kitchen utensils, dished, pots, and pans. There was a little hangout area/deck on top. Hate that we were so busy running around the state parks, that we didnt get time to enjoy it as much aa we could have. "
Village Camp Flagstaff
Exterior
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (66)
"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
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!
Exterior
Sonder Jewelers Row
3.5 star property
8.2 out of 10, Very good, (102)
"The entire experience was fantastic. Clear instructions in how to get into the building and the apartment, fully stocked kitchen and extremely comfortable bed"
The price is HK$1,531
per night
28 May - 29 May
Sonder Jewelers Row
1 bedroom, premium bedding, pillow-top beds, desk
WoodSpring Suites Chicago Addison
2.5 star property
6.0 out of 10, (184)
"ITS A VERY NICE AND UPBEAT ESTABLISHMENT.......I ENJOYED THE STAY ONLY THING I DIDNT LIKE WAS THERE HOUSE KEEPING SCHEDULE BUT OTHER THAN THAT ITS A NICE QUIET LOCATION WITH NICE PEOPLE"
The price is HK$703
per night
27 May - 28 May
WoodSpring Suites Chicago Addison
Private kitchen
Fort Marcy Hotel Suites by All Seasons Resort Lodging
3.0 star property
8.8 out of 10, Excellent, (2118)
"A very comfortable three room suite including kitchen. Short walk to downtown. We saved money by preparing some meals in the unit."
The price is HK$1,384
per night
25 Jun - 26 Jun
Fort Marcy Hotel Suites by All Seasons Resort Lodging
Individually decorated, individually furnished, desk, laptop workspace
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 HK$552
per night
30 May - 31 May
White House at Grand Central
Premium bedding, blackout curtains, iron/ironing board, free WiFi
Arbor Suites at the Mall
2.0 star property
7.4 out of 10, Good, (2119)
"This property is conveniently located in walking distance from the mall and dozens of restaurants and easy to get to right in the center of Springfield. The place was exceptionally clean and inviting, even though you can tell the place is older. It has all the amenities I needed on the inside for frequent stays in Springfield for business, including a kitchenette, refrigerator, microwave, range, and comfortable beds. "
The price is HK$626
per night
27 May - 28 May
Arbor Suites at the Mall
Interior
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

Exterior
Club Quarters Hotel, Central Loop, Chicago
4.0 star property
8.6 out of 10, Excellent, (3066)
"It’s so old and no air conditioning, but it’s sooo charming and historic. It served the purpose of the two nights we stayed. "
The price is HK$1,106
per night
27 May - 28 May
Club Quarters Hotel, Central Loop, Chicago
Exterior
Central Loop Hotel
4.0 star property
8.6 out of 10, Excellent, (1620)
"Easy option for visiting downtown Chicago "
The price is HK$1,106
per night
27 May - 28 May
Central Loop Hotel
Outdoor pool
The Aquarius Casino Resort, BW Premier Collection
3.5 star property
8.0 out of 10, Very good, (5858)
"One of the nicer places in Laughlin. "
The price is HK$383
per night
27 May - 28 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.

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