Holiday Rentals in Historic Route 66

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Holiday 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 €182
per night
28 May - 29 May
Sentral Michigan Avenue
Terrace/patio
Junipine Resort
3.5 star property
9.2 out of 10, Wonderful, (1793)
"We stayed here 10 years ago for our 30th anniversary. The property has not been updated and needs repairs. There was a spot on our deck that my foot went partially through. Beautiful scenery and birdwatching."
The price is €264
per night
9 Jun - 10 Jun
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 €107
per night
27 May - 28 May
Sonder Market Hall
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City view from property
Sonder South Wabash
3.5 star property
8.8 out of 10, Excellent, (298)
"Overall the stay was amazing. We will definitely be booking here again."
The price is €210
per night
27 May - 28 May
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, (231)
"The location was perfect, as well as The appartement!"
Kasa Magnificent Mile Chicago
Superior Loft | Private kitchen
Grand Canyon RV Glamping
1.5 star property
9.0 out of 10, Wonderful, (425)
"The front desk staff was friendly and informative. Provided extras and assured us if we had any issurs, that someone was onsite to help even after the office closed."
The price is €82
per night
23 May - 24 May
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 €227
per night
18 Jun - 19 Jun
Found Chicago powered by Sonder
Front of property – evening/night
Level Chicago – Old Town
4.0 star property
8.8 out of 10, Excellent, (207)
"Nice"
The price is €219
per night
27 May - 28 May
Level Chicago – Old Town
Exterior
Sonder The Burnham
3.5 star property
8.8 out of 10, Excellent, (58)
"It is next to Union Station. Downtown attractions are across the bridge. We loved the industrial decor. The wall is thin. You can hear people talking. It doesn’t bother us too much. Love Sonder!"
The price is €210
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, (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, 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 €88
per night
27 May - 28 May
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 €212
per night
28 May - 29 May
Sonder Jewelers Row
Exterior
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (65)
"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
Fort Marcy Hotel Suites by All Seasons Resort Lodging
3.0 star property
8.8 out of 10, Excellent, (2117)
"Away from busy town but within walking distance, just a hike up a hill. Areas that need attention are the leaking kitchen faucet and mold in bathroom near shower."
The price is €238
per night
26 May - 27 May
Fort Marcy Hotel Suites by All Seasons Resort Lodging
Comfort Apartment
White House at Grand Central
3.0 star property
9.0 out of 10, Wonderful, (70)
"Great place to stay, especially close to Saint Louis University. Communication was excellent, check-in was easy. Great value. "
The price is €135
per night
3 Jun - 4 Jun
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 curtains, iron/ironing board, free WiFi
Arbor Suites at the Mall
2.0 star property
7.4 out of 10, Good, (2114)
"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 €93
per night
29 May - 30 May
Arbor Suites at the Mall
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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, (3054)
"Dirty carpet, staff was rude and not flexible at all. "
The price is €163
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, (1614)
"The location is great. Staff was wonderful. There were some issues with the keys not working, but once that got fixed everything was great. The free bottled water was a nice touch."
The price is €155
per night
28 May - 29 May
Central Loop Hotel
Lobby
Congress Plaza Hotel
3.5 star property
7.6 out of 10, Good, (6783)
"Room was renovated, and very nice and clean. For an old hotel, this was a very nice experience!"
The price is €161
per night
27 May - 28 May
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.

Everything you need to know about Historic Route 66 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Historic Route 66 holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Historic Route 66 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Historic Route 66 holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Historic Route 66. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Historic Route 66 holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Historic Route 66 holiday rentals we have selected for you start as low as €82 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Historic Route 66 rentals

At Expedia, we put the best Historic Route 66 holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Historic Route 66 rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Historic Route 66 holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Historic Route 66. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Recent reviews of Historic Route 66 properties
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