Historic Route 66 Vacation Rentals

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Vacation Rentals in Historic Route 66

Interior
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (412)
"The front desk staff were incredibly helpful, cheerfully assisted me with check-in and stored my extra bags early in the day when I went to work on the day u checked out. A service."
The price is $159
$216 total
includes taxes & fees
May 27 - May 28
Sentral Michigan Avenue
Interior
Sonder Market Hall
3.5 star property
8.2 out of 10, Very Good, (85)
"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 $95
$112 total
includes taxes & fees
May 27 - May 28
Sonder Market Hall
City view from property
Sonder South Wabash
3.5 star property
8.8 out of 10, Excellent, (301)
"It was a pleasant stay"
The price is $194
$228 total
includes taxes & fees
May 28 - May 29
Sonder South Wabash
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49-inch Smart TV with digital channels, TV, streaming services
Kasa Magnificent Mile Chicago
4.0 star property
9.2 out of 10, Wonderful, (239)
"Clean, friendly, spacious and at an excellent location."
Kasa Magnificent Mile Chicago
Terrace/patio
Junipine Resort
3.5 star property
9.2 out of 10, Wonderful, (1795)
"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 $225
$256 total
includes taxes & fees
Jun 12 - Jun 13
Junipine Resort
Front of property - evening/night
Level Chicago – Old Town
4.0 star property
8.8 out of 10, Excellent, (208)
"Nice"
The price is $206
$259 total
includes taxes & fees
May 27 - May 28
Level Chicago – Old Town
Superior Loft | Private kitchen | Full-size fridge, microwave, oven, stovetop
Grand Canyon RV Glamping
1.5 star property
9.0 out of 10, Wonderful, (428)
"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 $64
$140 total
includes taxes & fees
May 30 - May 31
Grand Canyon RV Glamping
Interior
Found Chicago powered by Sonder
3.5 star property
7.6 out of 10, Good, (130)
"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 $205
$241 total
includes taxes & fees
Jun 18 - Jun 19
Found Chicago powered by Sonder
Exterior
Sonder The Burnham
3.5 star property
9.0 out of 10, Wonderful, (62)
" Cozy "
The price is $194
$228 total
includes taxes & fees
May 29 - May 30
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, (32)
"Great property, very clean, staff was only a message away and very friendly. Definitely recommend and would stay again. "
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
9.2 out of 10, Wonderful, (55)
"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
Exterior
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (66)
"The building was clean and attractive. Security on site. Breakfast options close by. All the best sites walking distance. Units was amazing. Kasa very engaged and accessible. River Walk, boat excursions etc. Tours etc. Right there. Rooftop pool and all amenities on site wow!"
Kasa River North Chicago
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, (102)
"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 $196
$230 total
includes taxes & fees
May 28 - May 29
Sonder Jewelers Row
1 bedroom, premium bedding, pillowtop beds, desk
WoodSpring Suites Chicago Addison
2.5 star property
6.0 out of 10, (184)
"Very nice property "
The price is $90
$95 total
includes taxes & fees
May 27 - May 28
WoodSpring Suites Chicago Addison
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, (2119)
"A very comfortable three room suite including kitchen. Short walk to downtown. We saved money by preparing some meals in the unit."
The price is $177
$259 total
includes taxes & fees
May 27 - May 28
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, (71)
"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 $71
$203 total
includes taxes & fees
May 30 - May 31
White House at Grand Central
Premium bedding, blackout drapes, iron/ironing board, free WiFi
Arbor Suites at the Mall
2.0 star property
7.4 out of 10, Good, (2119)
"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 $80
$91 total
includes taxes & fees
May 27 - May 28
Arbor Suites at the Mall
Interior
Historic, Renovated Fire Station Vacation Rental!
3.5 star property
Historic, Renovated Fire Station Vacation Rental!
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, (3069)
"Small room"
The price is $149
$175 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, (1620)
"Easy option for visiting downtown Chicago "
The price is $149
$175 total
includes taxes & fees
May 27 - May 28
Central Loop Hotel
Outdoor pool
The Aquarius Casino Resort, BW Premier Collection
3.5 star property
8.0 out of 10, Very Good, (5862)
"One of the nicer places in Laughlin. "
The price is $49
$79 total
includes taxes & fees
May 27 - May 28
The Aquarius Casino Resort, BW Premier Collection
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Historic Route 66 vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Historic Route 66 vacation 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 low season months. For more hustle and bustle, you may prefer to visit Historic Route 66 in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $64 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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 vacation 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 vacation.

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
Expedia verified reviews

The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

5/5 Excellent
"Everything was great besides it is an older building and older furniture they use. Our ac system did not work in our first room but we were able to get set up to a new room asap. The staff were friendly and helpful. It was easy to get to the subway and was a close walk to pretty much everything. "
A verified traveler stayed at The Whitehall Hotel, BW Premier Collection
Posted 4 hours ago
The Whitehall Hotel, BW Premier Collection