Overland Vacation Rentals

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Vacation Rentals in Overland

White House at Grand Central
4.0 star property
8.4 out of 10, Very Good, (122)
"It was very clean and nicely decorated. The house is a cool old building. The AC worked great (important, as it was super muggy outside.) I was only there for a couple nights but I think it would have worked well for a longer stay. "
United States
Sharon
$133 nightly
The price is $155
Nov 4 - Nov 5
Total with taxes and fees
White House at Grand Central
The St. Charles Guest House, lovely historic home, fun for families and groups
10.0 out of 10, Exceptional, (135)
"House is so charming and a home away from home! The historical home and town were literally the vacation I will cherish! Game room was a hit!I highly recommend for any family that plans to visit St. Charles, MO!"
United States
Schererville A.
The St. Charles Guest House, lovely historic home, fun for families and groups
Serene Living Downtown STL Loft
8.0 out of 10, Very Good, (11)
"The apartment, furniture, and kitchenware are clean. The apartment is spacious. I felt comfortable staying and sleeping there. "
United States
Thunyapong
$139 nightly
The price is $141
Nov 4 - Nov 5
Total with taxes and fees
Serene Living Downtown STL Loft
Charming 3-bedroom house with WiFi, AC in the heart of St. Louis
2.0 star property
8.4 out of 10, Very Good, (22)
"Excellent location very clean place "
United States
kimberly b.
$294 nightly
The price is $312
Nov 4 - Nov 5
Total with taxes and fees
Charming 3-bedroom house with WiFi, AC in the heart of St. Louis
Cozy Clark Suite in Frenchtown Saint Charles
9.4 out of 10, Exceptional, (10)
"Awesome place to stay"
United States
paul
$246 nightly
The price is $246
Nov 4 - Nov 5
Total with taxes and fees
Cozy Clark Suite in Frenchtown Saint Charles
Madison House 2 -Walk to Main St
8.8 out of 10, Excellent, (5)
"Poor communication with property owner we told him of issues including two ceiling fans not working missing lightbulbs broken coffee maker unusable backyard due to negligence old stove and broken chair in backyard dirty back porch he responded on the first day he would bring lightbulbs and never came even though he said he lived one block away "
United States
Tom B.
$224 nightly
The price is $252
Nov 9 - Nov 10
Total with taxes and fees
Madison House 2 -Walk to Main St
Classy Midtown 3BR, King Master
10.0 out of 10, Exceptional, (58)
"Our stay was great. Liked the open living, dining and kitchen area. Bedrooms were comfortable."
United States
Christina P.
$195 nightly
The price is $209
Nov 11 - Nov 12
Total with taxes and fees
Classy Midtown 3BR, King Master
Tamm Ave 3-BR Retreat
9.6 out of 10, Exceptional, (44)
"We enjoyed are stay at this house. It was very clean and comfortable. Host was very quick to respond and easy check in. Nice neighborhood, felt very safe. Would for sure stay here again!!"
United States
Cindy A.
Tamm Ave 3-BR Retreat
1830's Luxury Brick Cottage, Cozy Fireplace, right off the Cobblestone Streets!
10.0 out of 10, Exceptional, (209)
"Nice view of the Mississippi in the morning. Just off of the main street in old town St Charles, this place was perfect for our needs."
United States
Ralph
1830's Luxury Brick Cottage, Cozy Fireplace, right off the Cobblestone Streets!
Downtown STL Lovely Loft w/Pool/ Free Breakfast/Free Parking
6.6 out of 10, (9)
"First off, i want to say the price for the property was the reason i booked it. It was much cheaper than other options. I read the reviews and was mostly prepared for the property conditions. The day of check-in, you will receive a text with a link to unlock the various gates and doors for the property, and i had no issues with this. The parking spot that was listed in the automatic message was i correct. A neighbor came out and informed us that the parking spot listed was wrong and we would be...
United States
Bethany
$180 nightly
The price is $180
Nov 6 - Nov 7
Total with taxes and fees
Downtown STL Lovely Loft w/Pool/ Free Breakfast/Free Parking
Centrally located in the Tower Grove East neighborhood!
9.8 out of 10, Exceptional, (131)
"Great stay, comfortable furnishings, quiet street. "
United States
Tracy C.
$147 nightly
The price is $172
Nov 11 - Nov 12
Total with taxes and fees
Centrally located in the Tower Grove East neighborhood!
Stunning 1890's Home - Sleeps 8!
10.0 out of 10, Exceptional, (85)
"The house is beautiful, in a great location, and has all the amenities of home. Definitely glad we stayed here instead of a nearby hotel."
United States
Emily D.
$372 nightly
The price is $381
Nov 4 - Nov 5
Total with taxes and fees
Stunning 1890's Home - Sleeps 8!
The Hare Suite at Divine Otter
9.4 out of 10, Exceptional, (12)
"This is such a cute place. Highly recommend. Very relaxing while also all kinds of shopping and dining options. There was a water main break our first few hrs into the stay. Host was great responded fast to any questions we had. "
United States
Pam
The Hare Suite at Divine Otter
St. Charles 1860's Gem - Sleeps 6!
9.8 out of 10, Exceptional, (129)
"Great location to historic St. Charles! Lots of room and it was a great stay!"
United States
brooke c.
$251 nightly
The price is $251
Nov 11 - Nov 12
Total with taxes and fees
St. Charles 1860's Gem - Sleeps 6!
5th Street #1 · Historic 5th Street House - Fully Rehabbed # 1
9.0 out of 10, Wonderful, (10)
"Great property!!"
United States
Nicole S.
$211 nightly
The price is $237
Nov 4 - Nov 5
Total with taxes and fees
5th Street #1 · Historic 5th Street House - Fully Rehabbed # 1
At home near Lafayette Square Pet-Friendly
9.0 out of 10, Wonderful, (6)
"The house worked perfectly for our family of 5. The tall ceilings and large windows and skylights filling the space with natural light made it a very nice place to be. We enjoyed the games and the comfortable living room was great for movie night. Beds were very comfortable!We arrived just hours after the tornadoes struck downtown St Louis, and our host was super attentive and communicative as we waited for the city to restore power. We really appreciated his attentiveness and would definitely...
United States
Robin A.
At home near Lafayette Square Pet-Friendly
Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!
9.8 out of 10, Exceptional, (152)
"Clean, very nice host, cute little building. It was a little warm in there with the window unit but other wise it was amazing "
United States
Lindsay
$132 nightly
The price is $134
Nov 5 - Nov 6
Total with taxes and fees
Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!
Honky Tonk Hideaway
9.2 out of 10, Wonderful, (9)
"We were in town for a concert and loved our stay here. Great location very close to restaurants and bars. Very safe area. Had a very private back patio next to a creek which made morning coffee even better. Place was clean and had all the necessities. We will stay here again."
United States
LAURIE P.
$288 nightly
The price is $294
Nov 4 - Nov 5
Total with taxes and fees
Honky Tonk Hideaway
Retro Baseball Downtown Apartment
7.6 out of 10, Good, (5)
"Our stay at this house was 1 of the best! Completely updated unit- VRBO pictures & description are exact. Definitely will stay again! "
United States
Nancy C.
$197 nightly
The price is $204
Nov 7 - Nov 8
Total with taxes and fees
Retro Baseball Downtown Apartment
The Lewis & Clark Hangout
9.0 out of 10, Wonderful, (19)
"Close to down town and easy to get to. Communicate with home owner was very good! "
United States
Michelle L.
$333 nightly
The price is $374
Nov 6 - Nov 7
Total with taxes and fees
The Lewis & Clark Hangout
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 Overland Hotel Reviews

Find out more about Overland

Everything you need to know about Overland 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 Overland 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 Overland vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Overland vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Overland. 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 Overland 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 $134 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 Overland rentals

At Expedia, we put the best Overland 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 Overland 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 Overland 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 Overland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find vacation rentals in Overland?

Yes, we have vacation rentals close to top local attractions in Overland, or you can choose a more remote option if you want a relaxing place to stay. Overland is known for its live music and bars. Make sure you have time to check out the churches and coffeehouses during your trip.

What's the top vacation rental in Overland?

Madison House 2 -Walk to Main St: Visitors like this Overland vacation home rental. It is equipped with an arcade game room, air-conditioning, and WiFi to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Overland?

With 10 Expedia vacation rentals, you're sure to find just the right place for your Overland stay.

What can I see and do in Overland?

Explore the area and family-friendly sights such as St. Louis Zoo, or get out into nature at a spot like Forest Park. St. Louis Union Station and Busch Stadium are other popular places to visit in the area.

What are vacation rentals like in Overland?

Vacation rentals are privately owned properties you can stay in for several days or more in Overland. Vacation rentals offer extras such as patios, hot tubs, and fire pits so you'll be comfy for your stay. If you're concerned about cleanliness, a vacation rental can offer a sense of safety away from public hotel elevators and busy front desks while still allowing you to travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great choice for a family trip or a small group gathering.