Historic Route 66 Vacation Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Vacation Rentals in Historic Route 66

Interior
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (406)
"Great find!"
The price is ¥22,431
¥30,933 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, (1793)
"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 ¥39,362
¥44,833 total
includes taxes & fees
Jun 13 - Jun 14
Junipine Resort
Interior
Sonder Market Hall
3.5 star property
8.2 out of 10, Very Good, (83)
"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 ¥15,437
¥18,122 total
includes taxes & fees
May 27 - May 28
Sonder Market Hall
Save an average of 15% on thousands of hotels when you're signed in
City view from property
Sonder South Wabash
3.5 star property
8.8 out of 10, Excellent, (298)
"What a nice surprise. First time I have used Sonder. But will not be the last. Great value for the money. "
The price is ¥30,411
¥35,703 total
includes taxes & fees
May 28 - May 29
Sonder South Wabash
49-inch Smart TV with digital channels, TV, streaming services
Kasa Magnificent Mile Chicago
4.0 star property
9.2 out of 10, Wonderful, (233)
"The room was very clean and nice. A great option for downtown Chicago"
Kasa Magnificent Mile Chicago
Superior Loft | Private kitchen | Full-size fridge, microwave, oven, stovetop
Grand Canyon RV Glamping
1.5 star property
9.0 out of 10, Wonderful, (426)
"The weather was nice, good last minute booking"
The price is ¥12,685
¥25,144 total
includes taxes & fees
Jun 3 - Jun 4
Grand Canyon RV Glamping
Interior
Found Chicago powered by Sonder
3.5 star property
7.6 out of 10, Good, (129)
"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 ¥29,474
¥34,602 total
includes taxes & fees
Jun 18 - Jun 19
Found Chicago powered by Sonder
Front of property - evening/night
Level Chicago – Old Town
4.0 star property
8.8 out of 10, Excellent, (208)
"Nice"
The price is ¥32,137
¥40,393 total
includes taxes & fees
May 27 - May 28
Level Chicago – Old Town
Exterior
Sonder The Burnham
3.5 star property
8.8 out of 10, Excellent, (59)
"Other than the stairs going up from the entrance door, everything is perfect. "
The price is ¥30,413
¥35,705 total
includes taxes & fees
May 28 - May 29
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, (31)
"This is one of the best hotels I have ever stayed. Very clean, spacious, and everything is well-designed. Exceed my expectation in every aspect."
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
1 bedroom, premium bedding, pillowtop 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 ¥14,056
¥14,899 total
includes taxes & fees
May 26 - May 27
WoodSpring Suites Chicago Addison
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, (101)
"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 ¥30,718
¥36,061 total
includes taxes & fees
May 28 - May 29
Sonder Jewelers Row
Exterior
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (66)
"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
2-Bedroom Condominium | Private kitchen | Fridge, microwave, oven, stovetop
Fort Marcy Hotel Suites by All Seasons Resort Lodging
3.0 star property
8.8 out of 10, Excellent, (2117)
"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 ¥27,664
¥40,410 total
includes taxes & fees
May 24 - May 25
Fort Marcy Hotel Suites by All Seasons Resort Lodging
Comfort Apartment | 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 ¥11,028
¥31,531 total
includes taxes & fees
May 30 - May 31
White House at Grand Central
Interior
Historic, Renovated Fire Station Vacation Rental!
3.5 star property
Historic, Renovated Fire Station Vacation Rental!
Premium bedding, blackout drapes, iron/ironing board, free WiFi
Arbor Suites at the Mall
2.0 star property
7.4 out of 10, Good, (2116)
"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 ¥13,966
¥15,891 total
includes taxes & fees
May 28 - May 29
Arbor Suites at the Mall
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, (3057)
"Good location to downtown. Comfortable bed! I enjoyed eating at the Elephant and Castle. "
The price is ¥22,188
¥26,049 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, (1617)
"Central location. Close to the art museum. "
The price is ¥22,188
¥26,049 total
includes taxes & fees
May 28 - May 29
Central Loop Hotel
Lobby
Congress Plaza Hotel
3.5 star property
7.6 out of 10, Good, (6789)
"I enjoyed staying at the historical hotel but definitely the room could use a refresher."
The price is ¥23,296
¥27,353 total
includes taxes & fees
May 27 - May 28
Congress Plaza Hotel
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.

Search for holiday rentals in Historic Route 66 on Expedia! You can easily find your home rentals, villas, holiday apartments in Historic Route 66 using one of the methods below:

  • View our selection of featured holiday rentals in Historic Route 66
  • Use the map to find apartments and other holiday homes in the Historic Route 66 neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Historic Route 66 while they last

Look no further and take a look at our great range of rental properties in Historic Route 66!

Recent reviews of Historic Route 66 properties
Expedia verified reviews