Holiday Homes in Historic Route 66

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Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Historic Route 66 holiday homes

Property grounds
Terrace #1 | 2 BR/1BA | Join us in January | Flagstaff

Terrace #1 | 2 BR/1BA | Join us in January | Flagstaff

Terrace #1 | 2 BR/1BA | Join us in January | Flagstaff
Downtown Flagstaff
9.0 out of 10, Wonderful, (4)
"Nice place right near town, very convenient "
United States
Dan R.
The price is €604
includes taxes & fees
29 Dec - 30 Dec
Terrace #1 | 2 BR/1BA | Join us in January | Flagstaff
Smart TV
Terrace Main | 5BR/3BA |Join us in January | Flagstaff

Terrace Main | 5BR/3BA |Join us in January | Flagstaff

Terrace Main | 5BR/3BA |Join us in January | Flagstaff
Downtown Flagstaff
The price is €1,213
includes taxes & fees
19 Jan - 20 Jan 2026
Terrace Main | 5BR/3BA |Join us in January | Flagstaff
Property grounds
Secluded Studio-Style 1-Bed/1-Bath Poolhouse in Southern Hills/Tulsa

Secluded Studio-Style 1-Bed/1-Bath Poolhouse in Southern Hills/Tulsa

Secluded Studio-Style 1-Bed/1-Bath Poolhouse in Southern Hills/Tulsa
South Tulsa
10.0 out of 10, Exceptional, (30)
"The property was cozy and it's very clean"
United States
Jennifer L.
The price is €145
includes taxes & fees
1 Jan - 2 Jan 2026
Secluded Studio-Style 1-Bed/1-Bath Poolhouse in Southern Hills/Tulsa
Terrace/patio
Home is on the original 1926-1930 Route 66 alignment

Home is on the original 1926-1930 Route 66 alignment

Home is on the original 1926-1930 Route 66 alignment
Girard
10.0 out of 10, Exceptional, (97)
"The historic house was perfect for our vacation. "
United States
Kelly F.
The price is €150
includes taxes & fees
3 Jan - 4 Jan 2026
Home is on the original 1926-1930 Route 66 alignment
Fridge, microwave, oven, stovetop
Lyle &Taylor Present -Slice of Home on the Road

Lyle &Taylor Present -Slice of Home on the Road

Lyle &Taylor Present -Slice of Home on the Road
Bourbonnais
9.8 out of 10, Exceptional, (43)
"Very spacious & very clean. Loved the stayed."
United States
Rafael N.
The price is €133
includes taxes & fees
4 Jan - 5 Jan 2026
Lyle &Taylor Present -Slice of Home on the Road
Smart TV, fireplace, DVD player
The Cowskin Bunkhouse - Lakeview Getaway - perfect for fishermen/small families!

The Cowskin Bunkhouse - Lakeview Getaway - perfect for fishermen/small families!

The Cowskin Bunkhouse - Lakeview Getaway - perfect for fishermen/small families!
Grove
10.0 out of 10, Exceptional, (15)
"Wonderful place to stay! Very clean, cute and cozy! We will definitely be back!"
United States
Christie M.
The price is €117
includes taxes & fees
30 Dec - 31 Dec
The Cowskin Bunkhouse - Lakeview Getaway - perfect for fishermen/small families!
Exterior
Cozy Joplin home, near medical school

Cozy Joplin home, near medical school

Cozy Joplin home, near medical school
Joplin
10.0 out of 10, Exceptional, (125)
"House was as described, very comfortable and close to everything we wanted to do."
United States
Karen J.
The price is €140
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy Joplin home, near medical school
Interior
Escape to Wonderland

Escape to Wonderland

Escape to Wonderland
Central Oklahoma City
10.0 out of 10, Exceptional, (102)
"Great stay, property was very clean, fun, functional, and detail-oriented. My 7 year old daughter and I enjoyed our stay very much."
United States
Sara M.
The price is €187
includes taxes & fees
28 Dec - 29 Dec
Escape to Wonderland
Property grounds
Sunrise Bluff Lakefront - in family-friendly area w/ great view of Grand Lake

Sunrise Bluff Lakefront - in family-friendly area w/ great view of Grand Lake

Sunrise Bluff Lakefront - in family-friendly area w/ great view of Grand Lake
Grove
9.4 out of 10, Exceptional, (46)
"My drivers loved the property"
United States
Stacey
The price is €215
includes taxes & fees
28 Dec - 29 Dec
Sunrise Bluff Lakefront - in family-friendly area w/ great view of Grand Lake
Fridge, microwave, oven, stovetop
McClusky Trail Guesthouse Convenient Access to Jerseyville, Grafton & Alton

McClusky Trail Guesthouse Convenient Access to Jerseyville, Grafton & Alton

McClusky Trail Guesthouse Convenient Access to Jerseyville, Grafton & Alton
Jerseyville
10.0 out of 10, Exceptional, (21)
"Nicely appointed space, comfy beds, convenient location."
United States
Mike & JoAnn H.
The price is €189
includes taxes & fees
30 Dec - 31 Dec
McClusky Trail Guesthouse Convenient Access to Jerseyville, Grafton & Alton
Property grounds
The ClubHouse

The ClubHouse

The ClubHouse
Springfield
10.0 out of 10, Exceptional, (77)
"Stayed here multiple times, consistently clean and comfortable! Many nice extra touches!"
United States
Jamie B.
The price is €253
includes taxes & fees
12 Jan - 13 Jan 2026
The ClubHouse
Fridge, microwave, oven, stovetop
Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!

Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!

Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!
The Hill
9.8 out of 10, Exceptional, (160)
"Very clean, check in was easy, great neighborhood with lots of food close. "
United States
Laura H.
The price is €126
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!
Fridge, microwave, oven, stovetop
Get Cozy in the Country - The Cottage on Luca Hill

Get Cozy in the Country - The Cottage on Luca Hill

Get Cozy in the Country - The Cottage on Luca Hill
2.0 star property
Saint James
10.0 out of 10, Exceptional, (18)
"Nice clean property wirh a good location for us!"
United States
John P.
The price is €164
includes taxes & fees
28 Dec - 29 Dec
Get Cozy in the Country - The Cottage on Luca Hill
Smart TV, DVD player, books, video library
Very Cozy and Secluded. Completely remodeled beautiful back apartment

Very Cozy and Secluded. Completely remodeled beautiful back apartment

Very Cozy and Secluded. Completely remodeled beautiful back apartment
Springfield
10.0 out of 10, Exceptional, (60)
"We loved our 2 night stay. Such a quiet little corner. "
United States
Charlene C.
Very Cozy and Secluded. Completely remodeled beautiful back apartment
Interior
Unique Historic Charm ~ 5★ Location ~ Dreamy Porch Centrally Located

Unique Historic Charm ~ 5★ Location ~ Dreamy Porch Centrally Located

Unique Historic Charm ~ 5★ Location ~ Dreamy Porch Centrally Located
Ozark
9.8 out of 10, Exceptional, (74)
"Pleasing restored colonial era house in a quiet neighborhood. Would stay here again!"
United States
Jeff B.
The price is €253
includes taxes & fees
28 Dec - 29 Dec
Unique Historic Charm ~ 5★ Location ~ Dreamy Porch Centrally Located
Exterior
TJ’s Country Getaway- Dog Friendly

TJ’s Country Getaway- Dog Friendly

TJ’s Country Getaway- Dog Friendly
Union
10.0 out of 10, Exceptional, (45)
"My dog and I stayed for the week while attending our National Specialty at Purina Farms. I would definitely stay here again. Safe, quiet, peaceful and tons of amenities. 10/10!"
United States
Laura S.
The price is €120
includes taxes & fees
4 Jan - 5 Jan 2026
TJ’s Country Getaway- Dog Friendly
Property grounds
Serenity's Sanctuary in this quiet, peaceful 2 bdr 1 bath bungalow. Pet friendly

Serenity's Sanctuary in this quiet, peaceful 2 bdr 1 bath bungalow. Pet friendly

Serenity's Sanctuary in this quiet, peaceful 2 bdr 1 bath bungalow. Pet friendly
Cushing
9.8 out of 10, Exceptional, (60)
"We loved our stay! Had so much fun with the old arcade."
United States
Davi B.
The price is €88
includes taxes & fees
30 Dec - 31 Dec
Serenity's Sanctuary in this quiet, peaceful 2 bdr 1 bath bungalow. Pet friendly
Exterior
Ivy Jungalow | Bright, Clean, & near Downtown

Ivy Jungalow | Bright, Clean, & near Downtown

Ivy Jungalow | Bright, Clean, & near Downtown
Joplin
9.8 out of 10, Exceptional, (66)
"Thank you for a great stay!"
United States
April D.
The price is €155
includes taxes & fees
19 Jan - 20 Jan 2026
Ivy Jungalow | Bright, Clean, & near Downtown
Exterior detail
Cozy House On The HILL 10 Min from Ft. Leonard Wood

Cozy House On The HILL 10 Min from Ft. Leonard Wood

Cozy House On The HILL 10 Min from Ft. Leonard Wood
Waynesville
10.0 out of 10, Exceptional, (43)
"This is the second time my family has stayed here, and each time it has been cozy and family-friendly! We will for sure come again! "
United States
Karli
The price is €174
includes taxes & fees
28 Dec - 29 Dec
Cozy House On The HILL 10 Min from Ft. Leonard Wood
Interior
Centrally located in the Tower Grove East neighborhood!

Centrally located in the Tower Grove East neighborhood!

Centrally located in the Tower Grove East neighborhood!
Tower Grove East
9.8 out of 10, Exceptional, (139)
"Great little place and location was close to our event."
United States
RL T.
The price is €139
includes taxes & fees
29 Dec - 30 Dec
Centrally located in the Tower Grove East neighborhood!
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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Top Historic Route 66 Hotel Reviews

Hyatt Regency Chicago

Hyatt Regency Chicago

10/10 Excellent
"Stay was very pleasant and in close proximity to great shopping and dining. Will definitely stay here again in the future. "
CHARL 2-night trip
Posted 1 day ago
Hyatt Regency Chicago

Find out more about Historic Route 66

Historic Route 66 Holiday Homes information

Number of reviews
1,218
Accommodation
78 Holiday Homes
Lowest Price
€88
Highest Price
€1,213