Overland Vacation Rentals

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Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Overland vacation rentals

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White House at Grand Central

Apartment in Grand Center

White House at Grand Central
4.0 star property
8.6 out of 10, Excellent, (124)
"Very clean and very friendly people "
United States
Mary
$123 nightly
The price is $144
Jan 4 - Jan 5, 2026
Total with taxes and fees
White House at Grand Central
Exterior
The St. Charles Guest House, lovely historic home, fun for families and groups

Vacation Home in St. Charles Historic District

The St. Charles Guest House, lovely historic home, fun for families and groups
10.0 out of 10, Exceptional, (136)
"We loved staying here in this adorable clean house that was only 1 block off of downtown Main Street shopping. "
United States
Lisa S.
The St. Charles Guest House, lovely historic home, fun for families and groups
Studio Suite, 1 King Bed | Desk, laptop workspace, blackout drapes, WiFi
Value Suites Extended Stay - St Louis

Aparthotel in Maryland Heights

Value Suites Extended Stay - St Louis
3.0 star property
7.0 out of 10, Good, (1110)
"We’ve stayed here twice before and have always been pleased with everything. Very good hotel close to what we need."
United States
Timothy
$453 nightly
The price is $525
Dec 13 - Dec 14
Total with taxes and fees
Value Suites Extended Stay - St Louis
Fridge, microwave, oven, stovetop
Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!

Vacation Home in The Hill

Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!
9.8 out of 10, Exceptional, (160)
"Very clean, check in was easy, great neighborhood with lots of food close. "
United States
Laura H.
$132 nightly
The price is $134
Dec 14 - Dec 15
Total with taxes and fees
Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!
Microwave, oven, stovetop, dishwasher
Stunning 1890's Home - Sleeps 8!

Vacation Home in St. Charles Historic District

Stunning 1890's Home - Sleeps 8!
10.0 out of 10, Exceptional, (102)
"Check-in was easy and the house was lovely "
United States
Delfino A.
$333 nightly
The price is $340
Dec 23 - Dec 24
Total with taxes and fees
Stunning 1890's Home - Sleeps 8!
Dining
Luxury 2BEDROOM LOFT near Bush Stadium

Apartment in Downtown St. Louis

Luxury 2BEDROOM LOFT near Bush Stadium
9.4 out of 10, Exceptional, (6)
"The location was perfect to access all things Downtown! The space was clean and well furnished. Check in/out was a breeze and the included parking spot was a huge plus for us! Great place to stay! "
United States
Kelci Y.
Luxury 2BEDROOM LOFT near Bush Stadium
Outdoor dining
1830's Luxury Brick Cottage, Cozy Fireplace, right off the Cobblestone Streets!

Cottage in St. Charles Historic District

1830's Luxury Brick Cottage, Cozy Fireplace, right off the Cobblestone Streets!
10.0 out of 10, Exceptional, (211)
"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!
Smart TV
Cozy Clark Suite in Frenchtown Saint Charles

Apartment in St. Charles Historic District

Cozy Clark Suite in Frenchtown Saint Charles
9.6 out of 10, Exceptional, (14)
"Awesome place to stay"
United States
paul
Cozy Clark Suite in Frenchtown Saint Charles
TV, books
St. Charles 1860's Gem - Sleeps 6!

Vacation Home in St. Charles Historic District

St. Charles 1860's Gem - Sleeps 6!
9.8 out of 10, Exceptional, (134)
"This was such a cute historical home and was perfect for our weekend in St Charles!"
United States
Isabelle C.
$251 nightly
The price is $251
Dec 14 - Dec 15
Total with taxes and fees
St. Charles 1860's Gem - Sleeps 6!
Microwave, oven, stovetop, dishwasher
Stylish City Reno Retreat!

Apartment in Hyde Park

Stylish City Reno Retreat!
6.4 out of 10, (15)
"We were pleased with our stay and would stay again"
United States
Nicole L.
Stylish City Reno Retreat!
Outdoor dining
Honky Tonk Hideaway

Vacation Home in St. Charles Historic District

Honky Tonk Hideaway
8.8 out of 10, Excellent, (12)
"Great location close to historic district."
United States
Hugh S.
$313 nightly
The price is $320
Dec 25 - Dec 26
Total with taxes and fees
Honky Tonk Hideaway
Fridge, microwave, oven, stovetop
Home Near Main Street-Covered Patio-Hot Tub!

Vacation Home in Saint Charles

Home Near Main Street-Covered Patio-Hot Tub!
9.8 out of 10, Exceptional, (26)
"The place was great! "
United States
Melissa I.
$443 nightly
The price is $452
Dec 15 - Dec 16
Total with taxes and fees
Home Near Main Street-Covered Patio-Hot Tub!
Game room
Madison House 1 -Walk to Main St

Vacation Home in St. Charles Historic District

Madison House 1 -Walk to Main St
8.6 out of 10, Excellent, (14)
"The house was clean and well stocked, location was great, and plenty of street parking. "
United States
Brad K.
$209 nightly
The price is $235
Dec 14 - Dec 15
Total with taxes and fees
Madison House 1 -Walk to Main St
Smart TV
Tamm Ave 3-BR Retreat

Vacation Home in Dogtown

Tamm Ave 3-BR Retreat
9.6 out of 10, Exceptional, (48)
"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
Fridge, microwave, oven, coffee/tea maker
Stylish South City King 1BR Apt

Apartment in Marine Villa

Stylish South City King 1BR Apt
2.0 star property
10.0 out of 10, Exceptional, (9)
"Great location, great accommodations, great host."
United States
Scott W.
$165 nightly
The price is $179
Dec 14 - Dec 15
Total with taxes and fees
Stylish South City King 1BR Apt
2 bedrooms, iron/ironing board, travel crib, WiFi
Residence on the Roundabout

Vacation Home in St Charles

Residence on the Roundabout
9.4 out of 10, Exceptional, (144)
"House was very nice. Pictures were good and we knew what to expect. Location was great for where we wanted to go.Owner was punctual when we had any questions!"
United States
Anne L.
Residence on the Roundabout
Smart TV
New Remodel in St. Charles - Sleeps 10! New patio! Large Fenced-in backyard!

Vacation Home in St. Charles Historic District

New Remodel in St. Charles - Sleeps 10! New patio! Large Fenced-in backyard!
9.6 out of 10, Exceptional, (62)
"We had a great weekend and enjoyed the house very much! We had everything we needed!"
United States
Laurie S.
$412 nightly
The price is $420
Dec 14 - Dec 15
Total with taxes and fees
New Remodel in St. Charles - Sleeps 10! New patio! Large Fenced-in backyard!
2 bedrooms, desk, iron/ironing board, free WiFi
The Otter Suite at Divine Otter

Aparthotel in St. Charles Historic District

The Otter Suite at Divine Otter
9.0 out of 10, Wonderful, (7)
"We absolutely loved this place! I would recommend this place. We had one issue but it was resolved. If you have children, I would probably stay somewhere else. There are bars all around and gets loud at night but it does get really quiet after 1:30 a.m. The property manager was absolutely amazing and is very quick to respond to your needs. "
United States
kim F.
The Otter Suite at Divine Otter
Exterior
Brand New! Soulard Charmer - Pet Friendly.

Vacation Home in Soulard

Brand New! Soulard Charmer - Pet Friendly.
9.6 out of 10, Exceptional, (24)
"This house was beautiful and in a very nice spot in St. Louis. Close to everything and the hosts were amazing. Would definitely use again "
United States
Justin B.
$261 nightly
The price is $261
Dec 14 - Dec 15
Total with taxes and fees
Brand New! Soulard Charmer - Pet Friendly.
TV
Spacious 2 BR Balcony Hideaway

Apartment in Northampton

Spacious 2 BR Balcony Hideaway
8.0 out of 10, Very Good, (15)
"Great stay! Management was easy to reach and very helpful when we couldnt find the correct wifi network. Nice place, would stay again."
United States
Bob C.
Spacious 2 BR Balcony Hideaway
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

21C Museum Hotel St Louis

21C Museum Hotel St Louis

10/10 Excellent
"The hotel is beautiful! It was a great pick for so much to do on the property. From the pool area with hot tub and saunas . To the art gallery, and the stubbing bar! Grab some fantastic cocktails! Ask for Sunday, she was wonderful bartending! Perfect stay."
Ashton 2-night trip
Posted 20 hours ago
21C Museum Hotel St Louis

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.

Explore a world of travel with Expedia

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?

Stunning 1890's Home - Sleeps 8! : Visitors like this Overland vacation home rental. It is equipped with a barbecue grill, air-conditioning, and laundry facilities to help you feel comfortable during your stay. It has 4 bedrooms as well as a kitchen with a dishwasher, a stovetop, and a microwave, so you can cook with friends or family.

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 Gateway Arch 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.