Historic Route 66 Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Nov 13 - Nov 14
Tomorrow
Nov 14 - Nov 15
This weekend
Nov 14 - Nov 16
Next weekend
Nov 21 - Nov 23

Vacation Rentals in Historic Route 66

Indoor pool
Sentral Michigan Avenue

Sentral Michigan Avenue

4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (983)
"Loved my stay! Staff was amazing and the apartment had everything to make you feel like home. "
United States
Nicole
The price is P6,993
P9,945 total
includes taxes & fees
Dec 7 - Dec 8
Sentral Michigan Avenue
49-inch Smart TV with digital channels, TV, streaming services
Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (615)
"Room was very nice, location was wonderful."
United States
Nicholas
Kasa Magnificent Mile Chicago
Front of property - evening/night
Level Chicago – Old Town

Level Chicago – Old Town

4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (378)
"Property was clean, centrally located with wonderful staff. Will definitely stay again."
United States
Michelle
Level Chicago – Old Town
1 bedroom, individually decorated, individually furnished, desk
Sonder by Marriott Bonvoy Market Hall Apartments West Loop

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

3.5 star property
Downtown Chicago
8.0 out of 10, Very Good, (400)
"Quite and low key spot"
United States
Shunica
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Terrace/patio
Junipine Resort

Junipine Resort

3.5 star property
Sedona
9.2 out of 10, Wonderful, (2221)
"The staff was extremely friendly and the area was beautiful."
United States
Destiney
The price is P13,513
P15,527 total
includes taxes & fees
Nov 30 - Dec 1
Junipine Resort
Lobby
Sonder by Marriott Bonvoy The Burnham Apartments Loop

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (253)
"Great stay. "
United States
Teresa
Sonder by Marriott Bonvoy The Burnham Apartments Loop
36-inch flat-screen TV with digital channels, TV
Sonder by Marriott Bonvoy South Wabash Apartments South Loop

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

3.5 star property
Near South Side
8.6 out of 10, Excellent, (712)
"Love the unit and location close to multiple restaurants and shopping."
United States
Jessie
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
Balcony
Kasa South Loop Chicago

Kasa South Loop Chicago

4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (372)
"An excellent place to stay in Chicago downtown."
United States
ABDULHAFEEZ
Kasa South Loop Chicago
Front of property
The Neighborhood Hotel-Little Italy

The Neighborhood Hotel-Little Italy

4.0 star property
Near West Side
9.6 out of 10, Exceptional, (218)
"This hotel is a 10 out of 10 for me! The hotel room was clean and the location was great. When I come back next year I’m definitely coming back here "
United States
Amonee
The Neighborhood Hotel-Little Italy
1 bedroom, individually furnished, desk, iron/ironing board
Sonder by Marriott Bonvoy The Opal Apartments River North

Sonder by Marriott Bonvoy The Opal Apartments River North

3.5 star property
Downtown Chicago
8.4 out of 10, Very Good, (57)
"Great location. Apartment had all the amenities needed. Felt safe. Only not so good part was that being in downtown, it wasn't super quiet at times. Would stay here again without a doubt."
United States
Swastika
Sonder by Marriott Bonvoy The Opal Apartments River North
50-inch flat-screen TV with digital channels, TV
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

3.5 star property
Downtown Chicago
8.2 out of 10, Very Good, (188)
"Place was amazing! Very centralized, all sorts of restaurants nearby, and right next to the CTA Trains which is AWESOME!"
United States
Alexander
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Business center
Kasa River North Chicago

Kasa River North Chicago

4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (176)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Living area
Wrigleyville Suites

Wrigleyville Suites

2.0 star property
Lakeview
9.6 out of 10, Exceptional, (25)
"Excellent location and very clean! Would stay again!"
United States
Jacob
The price is P10,067
P11,818 total
includes taxes & fees
Nov 14 - Nov 15
Wrigleyville Suites
Property grounds
Fort Marcy Hotel Suites by All Seasons Resort Lodging

Fort Marcy Hotel Suites by All Seasons Resort Lodging

3.0 star property
Northeast Santa Fe
8.8 out of 10, Excellent, (2217)
"It was an incredible stay, but for some of the rooms, there are lotta stairs. We loved it, will be back!"
United States
Ethan
The price is P7,033
P11,857 total
includes taxes & fees
Nov 16 - Nov 17
Fort Marcy Hotel Suites by All Seasons Resort Lodging
Private kitchen
The Gem Museum Suites

The Gem Museum Suites

3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (95)
"Great stay. The studio is small but has everything necessary."
United States
Julia
The price is P10,760
P12,318 total
includes taxes & fees
Nov 23 - Nov 24
The Gem Museum Suites
Exterior
All Towne Suites

All Towne Suites

2.0 star property
St. Robert
9.2 out of 10, Wonderful, (309)
"Clean room, sweet staff, good parking availability, had a full size frig. Very quiet location. Nearby diner was great! "
United States
Linda
The price is P4,741
P5,320 total
includes taxes & fees
Nov 14 - Nov 15
All Towne Suites
Interior
Bullhead City Home w/ Private Pool, Hot Tub & View

Bullhead City Home w/ Private Pool, Hot Tub & View

3.0 star property
Sunridge Estates
Bullhead City Home w/ Private Pool, Hot Tub & View
Desk, laptop workspace, blackout drapes, free WiFi
Comfort Inn Chicago Southland I-80 & I-294 Near Casino

Comfort Inn Chicago Southland I-80 & I-294 Near Casino

3.0 star property
Harvey
3.8 out of 10, (66)
"This place looked like a whole in the wall I didn’t even stay the place was so dirty and I could not receive a refund looks disgusting and not even worth a $50 stay at minimum. "
United States
Bria
The price is P4,989
P5,636 total
includes taxes & fees
Nov 17 - Nov 18
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Private kitchen
Grand Canyon RV Glamping

Grand Canyon RV Glamping

1.5 star property
Williams
8.8 out of 10, Excellent, (601)
"This place was amazing. Kids and the dog had a blast "
United States
chris
The price is P7,069
P8,334 total
includes taxes & fees
Dec 14 - Dec 15
Grand Canyon RV Glamping
BBQ/picnic area
MainStay Suites Springfield South - Battlefield Rd

MainStay Suites Springfield South - Battlefield Rd

2.0 star property
Bradford Park
8.8 out of 10, Excellent, (79)
"Clean, friendly"
United States
joe
The price is P5,463
P6,201 total
includes taxes & fees
Dec 1 - Dec 2
MainStay Suites Springfield South - Battlefield Rd
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Historic Route 66 Hotel Reviews

The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

10/10 Excellent
"10/10 Highly Recommend! "
Jai 1-night trip
Posted 2 days ago
The Whitehall Hotel, BW Premier Collection

Find out more about Historic Route 66

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!