Compare Historic Route 66 Guest House Rentals

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Featured Guest Houses in Historic Route 66

Villa Dubois Guest House

Villa Dubois Guest House

2 out of 5
3722 S Calumet Ave Chicago IL
$75 nightly
The price is $88 total per night
$88 total
Dec 19 - Dec 20
Total with taxes and fees
Villa Dubois Guest House features free WiFi in public areas, coffee in a common area, and microwave in a common area. If you plan to drive, free parking is available. Helpful staff can provide luggage storage and a safe deposit box at the front desk. Additional amenities include a refrigerator in a common area, express check-in, and express check-out.
Mccormick Place Guest House

Mccormick Place Guest House

3 out of 5
3643 South Indiana Avenue Chicago IL
$75 nightly
The price is $88 total per night
$88 total
Dec 19 - Dec 20
Total with taxes and fees
Mccormick Place Guest House features free WiFi in public areas and a garden. You can take advantage of free parking if you drive. Additional amenities include barbecue grills and a picnic area.
Parking included
Free WiFi
Chicago Avenue Inn

Chicago Avenue Inn

2 out of 5
3305 W Chicago Ave Chicago IL
$111 nightly
The price is $127 total per night
$127 total
Jan 12 - Jan 13, 2026
Total with taxes and fees
Chicago Avenue Inn features free WiFi in public areas, microwave in a common area, and refrigerator in a common area.
Grand Center Inn

Grand Center Inn

3 out of 5
3716 Grandel Square St. Louis MO
$177 nightly
The price is $209 total per night
$209 total
Dec 22 - Dec 23
Total with taxes and fees
Guest of Grand Center Inn enjoy features like meeting rooms, microwave in a common area, and refrigerator in a common area. Free parking is available if you drive. Front-desk staff can help with concierge services, and provide local restaurant recommendations. Additional amenities include a meeting room, express check-out, and wedding services.
Parking included
Free WiFi
Painted Lady Bed & Brew

Painted Lady Bed & Brew

3.5 out of 5
1100 Bellamah Ave NW Albuquerque NM
Free Cancellation
Reserve now, pay when you stay
$206 nightly
The price is $238 total per night
$238 total
Jan 11 - Jan 12, 2026
Total with taxes and fees
A local mainstay since 1881, Painted Lady Bed & Brew offers free WiFi in public areas, express check-out, and a terrace. If you drive, take advantage of free parking. Additional amenities include a garden and a picnic area.
Pet friendly
Parking included
Private Nature Getaway in the Pines

Private Nature Getaway in the Pines

Flagstaff AZ
At this guesthouse, guests have access to features like laundry facilities. This smoke-free guesthouse also has barbecue grills.
Pet friendly
Free WiFi
Wrigleyville Inn

Wrigleyville Inn

3 out of 5
914 W Newport Ave Chicago IL
Guests of Wrigleyville Inn enjoy free WiFi in public areas, a terrace, and laundry facilities. Free parking is included with your stay.
Casa de Tres Lunas

Casa de Tres Lunas

3 out of 5
719 Paseo De Peralta Santa Fe NM
Casa de Tres Lunas features free WiFi in public areas, express check-in, and express check-out. Airport transportation is made easy with an airport shuttle (available on request) for USD 46.00 per person one-way. Staff members are on hand to provide concierge services and a safe deposit box at the front desk. Additional amenities include barbecue grills and a garden.
Cozy, Fun, and One-Of-A-Kind!

Cozy, Fun, and One-Of-A-Kind!

St. Louis MO
$123 nightly
The price is $142 total per night
$142 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
This guesthouse is a smoke-free guesthouse.
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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.

Hotel Options in Historic Route 66

    Club Quarters Hotel, Central Loop, Chicago

    Club Quarters Hotel, Central Loop, Chicago

    111 West Adams Street Chicago IL
    $87 nightly
    The price is $102 total per night from Dec 24 to Dec 25
    $102 total
    Dec 24 - Dec 25
    Total with taxes and fees
    8.6/10 Excellent! (3,314 reviews)
    Hilton Chicago/Magnificent Mile Suites

    Hilton Chicago/Magnificent Mile Suites

    198 E Delaware Pl Chicago IL
    $89 nightly
    The price is $105 total per night from Jan 5 to Jan 6
    $105 total
    Jan 5 - Jan 6, 2026
    Total with taxes and fees
    8.8/10 Excellent! (3,504 reviews)
    Silversmith Hotel Chicago Downtown

    Silversmith Hotel Chicago Downtown

    10 S Wabash Ave Chicago IL
    $127 nightly
    The price is $149 total per night from Dec 27 to Dec 28
    $149 total
    Dec 27 - Dec 28
    Total with taxes and fees
    9.2/10 Wonderful! (2,133 reviews)

Historic Route 66 Guest Houses essential information

Accommodation
11 Guest Houses
Lowest Price
$88
Highest Price
$238
Popular accommodation
Villa Dubois Guest House, Mccormick Place Guest House, Chicago Avenue Inn, Grand Center Inn, Painted Lady Bed & Brew, Private Nature Getaway in the Pines, Wrigleyville Inn, Casa de Tres Lunas, Cozy, Fun, and One-Of-A-Kind!

More to Explore