Overland Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Overland vacation rentals

A living room with a fireplace, a television, and a sofa.

1. Beautiful 4-bedroom house Central to St. Louis and St. Charles

Beautiful 4-bedroom house Central to St. Louis and St. Charles
St. Louis
8.2 out of 10, Very good, (44 reviews)
"Good price for a four bedroom home."
United States
BRAD R.
The price is CA $210
CA $462 total
includes taxes & fees
Nov 9 - Nov 10
Beautiful 4-bedroom house Central to St. Louis and St. Charles
A compact kitchen with white cabinets, a stainless steel refrigerator, a coffee maker, and a hanging pendant light.

2. Convenience 2 Bedroom House to Explore All of St Louis

Convenience 2 Bedroom House to Explore All of St Louis
University City
10.0 out of 10, Exceptional, (55 reviews)
"The house was immaculately clean and beds were extremely comfortable!"
United States
Anna M.
The price is CA $165
CA $359 total
includes taxes & fees
Nov 29 - Nov 30
Convenience 2 Bedroom House to Explore All of St Louis
Free breakfast available on-site.

3. Great for Business Travelers! Comfortable Suite in St. Louis | BBQ Area

Great for Business Travelers! Comfortable Suite in St. Louis | BBQ Area
Westport
9.8 out of 10, Exceptional, (6 reviews)
"Everything from the staff to the amenities to the rooms were amazing! Definitely recommend staying here! "
Canada
Lashon C.
The price is CA $327
CA $392 total
includes taxes & fees
Nov 29 - Nov 30
Great for Business Travelers! Comfortable Suite in St. Louis | BBQ Area
A modern kitchen with a stone accent wall, a central island, and pendant lighting.

4. Lots of Space! Central to St Charles and STL. Newly Remodeled. Large Backyard!

Lots of Space! Central to St Charles and STL. Newly Remodeled. Large Backyard!
Pinehurst
8.6 out of 10, Excellent, (38 reviews)
"Great Stay!!!"
United States
David C.
The price is CA $314
CA $1,002 total
includes taxes & fees
Nov 11 - Nov 12
Lots of Space! Central to St Charles and STL. Newly Remodeled. Large Backyard!
A hotel room with a bed, a desk, a chair, a lamp, and a telephone.

5. 1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed

1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed
Westport
9.4 out of 10, Exceptional, (43 reviews)
"Great spot!"
United States
Anonymous traveller
The price is CA $78
CA $90 total
includes taxes & fees
Nov 11 - Nov 12
1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed
A spacious foyer with a grand staircase, a piano, and a large rug.

6. White House at Grand Central

White House at Grand Central
3.5 star property
Grand Center
8.2 out of 10, Very good, (168 reviews)
"Very spacious clean old house apartments"
United States
Priscilla
The price is CA $107
CA $174 total
includes taxes & fees
Nov 9 - Nov 10
White House at Grand Central
Living area

7. 6655 1N | Elegance Near the St. Louis Arch

6655 1N | Elegance Near the St. Louis Arch
Dogtown
7.8 out of 10, Good, (34 reviews)
"I loved the security aspect of this rental. Felt very safe and it is very close to Forest park which is amazing"
United States
heather d.
The price is CA $112
CA $199 total
includes taxes & fees
Nov 9 - Nov 10
6655 1N | Elegance Near the St. Louis Arch
A bedroom with a bed, bedside table, and a large painting on the wall.

8. 6649 1E | Garden Style Studio Near Forest Park

6649 1E | Garden Style Studio Near Forest Park
Dogtown
8.0 out of 10, Very good, (25 reviews)
"Very cute and cozy. Nice to be close to everything. "
United States
Dhgirlie H.
6649 1E | Garden Style Studio Near Forest Park
A modern living room with a dark wood floor, a leather sofa, and a fluffy rug.

9. 3BR Dogtown Bungalow |Office + Bar

3BR Dogtown Bungalow |Office + Bar
Dogtown
9.4 out of 10, Exceptional, (41 reviews)
"We loved our stay! The location was fantastic and perfect for our family of five."
United States
Laura F.
The price is CA $157
CA $482 total
includes taxes & fees
Nov 23 - Nov 24
3BR Dogtown Bungalow |Office + Bar
A living room with a white sofa, a black sofa, a glass coffee table, and a cityscape painting.

10. 6653 2S | Jewel of Central St. Louis

6653 2S | Jewel of Central St. Louis
Dogtown
8.0 out of 10, Very good, (26 reviews)
"Hot water was an issue. Other than that great place to stay"
United States
Ashley C.
The price is CA $112
CA $199 total
includes taxes & fees
Nov 9 - Nov 10
6653 2S | Jewel of Central St. Louis
A living room with a fireplace, a sofa, a coffee table, and a rug.

11. Updated Brick Home Sleep 9 Walk to WashU/Barnes/Delmar Loop/Forest Park/Zoo

Updated Brick Home Sleep 9 Walk to WashU/Barnes/Delmar Loop/Forest Park/Zoo
Skinker DeBaliviere
8.6 out of 10, Excellent, (14 reviews)
"Lovely place, great location. The floors are very creeky, so if you need a lot of quiet during the night be prepared. "
United States
Thomas J.
The price is CA $307
CA $911 total
includes taxes & fees
Nov 11 - Nov 12
Updated Brick Home Sleep 9 Walk to WashU/Barnes/Delmar Loop/Forest Park/Zoo
A hotel lobby with a staircase, a reception desk, and a seating area.

12. 2 Queen Beds | Mobil Access Tub Nsmk Kitchen

2 Queen Beds | Mobil Access Tub Nsmk Kitchen
Westport
9.6 out of 10, Exceptional, (46 reviews)
"Great place to stay!"
United States
Anonymous traveller
The price is CA $79
CA $91 total
includes taxes & fees
Nov 24 - Nov 25
2 Queen Beds | Mobil Access Tub Nsmk Kitchen
A modern kitchen with a built-in refrigerator, a dining area with a wooden table and benches, a gray sofa, and large windows providing natural light.

13. Chic Minimalist Gem w/ Fenced Backyard + W/D

Chic Minimalist Gem w/ Fenced Backyard + W/D
Princeton Heights
9.4 out of 10, Exceptional, (21 reviews)
"Very nice, clean, modern apartment in a safe, quiet, suburban neighborhood. We were very happy with our stay there for our visit to WashU and St. Louis."
United States
Dave
The price is CA $92
CA $274 total
includes taxes & fees
Nov 10 - Nov 11
Chic Minimalist Gem w/ Fenced Backyard + W/D
A modern kitchen with a built-in refrigerator, dining area with a table and chairs, a sofa, and a TV mounted on the wall.

14. Chic 2BR Gem | TG Park | Patio+Yard+W/D+Workspace

Chic 2BR Gem | TG Park | Patio+Yard+W/D+Workspace
Tower Grove South
The price is CA $108
CA $470 total
includes taxes & fees
Nov 12 - Nov 13
Chic 2BR Gem | TG Park | Patio+Yard+W/D+Workspace
A modern kitchen with a brick accent wall, stainless steel appliances, and a wooden countertop.

15. Classy Midtown 2BR, King Master

Classy Midtown 2BR, King Master
The Gate
10.0 out of 10, Exceptional, (89 reviews)
"Beautiful, peaceful stay!"
United States
Robin
The price is CA $129
CA $289 total
includes taxes & fees
Nov 30 - Dec 1
Classy Midtown 2BR, King Master
A modern kitchen with stainless steel appliances, white cabinetry, and a brick accent wall.

16. Historic Main St. Customs House Upstairs Apartment

Historic Main St. Customs House Upstairs Apartment
St. Charles Historic District
9.6 out of 10, Exceptional, (39 reviews)
"Lovely place to stay!"
United States
Margaret A.
The price is CA $174
CA $485 total
includes taxes & fees
Nov 9 - Nov 10
Historic Main St. Customs House Upstairs Apartment
A set of stone steps leading to a garage with a car parked inside.

17. Studio, sleeps 5, short drive to Hidden Valley Ski Resort, parks &concert venues

Studio, sleeps 5, short drive to Hidden Valley Ski Resort, parks &concert venues
Ballwin
8.0 out of 10, Very good, (25 reviews)
"Rooms were clean and everything we needed for our stay."
United States
Keith K.
The price is CA $95
CA $195 total
includes taxes & fees
Nov 9 - Nov 10
Studio, sleeps 5, short drive to Hidden Valley Ski Resort, parks &concert venues
A room with a dining table and chairs, a white door with glass panels, and hardwood flooring.

18. Charming Tower Grove Flat-Steps to T.G Park+Grand

Charming Tower Grove Flat-Steps to T.G Park+Grand
Tower Grove East
9.0 out of 10, Wonderful, (26 reviews)
"Great location, responsive host & perfect for our short stay! "
United States
Bekah K.
The price is CA $82
CA $261 total
includes taxes & fees
Nov 16 - Nov 17
Charming Tower Grove Flat-Steps to T.G Park+Grand
An outdoor hot tub area with seating and a covered patio.

19. Private Basement - Two King Beds and Hot Tub

Private Basement - Two King Beds and Hot Tub
Saint Charles
9.6 out of 10, Exceptional, (5 reviews)
"Clean. The patio was very comfortable and nice to sit and relax. The beds were also very comfortable."
United States
Beth S.
The price is CA $119
CA $462 total
includes taxes & fees
Nov 9 - Nov 10
Private Basement - Two King Beds and Hot Tub
A neatly made bed with a stack of folded towels, a bedside lamp, and a ceiling fan in a room with a large window and a wall-mounted artwork.

20. Home Near Main with Pet-Friendly Yard and Office

Home Near Main with Pet-Friendly Yard and Office
St. Charles Historic District
10.0 out of 10, Exceptional, (13 reviews)
"Very close to downtown St. Charles and the Kati Trail. The home is cute and bed is comfortable. Easy check in process and fenced in back yard was nice to have."
United States
Jessica S.
The price is CA $160
CA $368 total
includes taxes & fees
Nov 9 - Nov 10
Home Near Main with Pet-Friendly Yard and Office
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

A modern hotel room with a dining area, wooden cabinets, a checkered floor, and a flat-screen TV.
Wingate by Wyndham St. Louis Airport

Wingate by Wyndham St. Louis Airport

Wingate by Wyndham St. Louis Airport
St. Ann

10/10 Excellent

Great staff
Canada
Steve
Reviewed October 6, 2026
Wingate by Wyndham St. Louis Airport

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, cottages, 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 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 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 Overland vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Overland vacation rentals we have selected for you start as low as CA $77 per night. Entering your travel dates in the search wizard 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 where you'll be just 6.2 mi (9.9 km) from St. Louis Zoo, providing a more remote option if you'd like a quiet spot 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?

Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!: Visitors like this Overland vacation home rental. It is located in the city center and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Overland?

With 7 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 Car Museum and St. Louis Union Station are a couple of places you'll find in the larger 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.