Overland Holiday Rentals

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Holiday Rentals in Overland

White House at Grand Central

4.0 star property
Grand Center
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
The price is NZ$274
includes taxes & fees
8 Dec - 9 Dec
White House at Grand Central

The St. Charles Guest House, lovely historic home, fun for families and groups

St. Charles Historic District
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

Downtown West
7.6 out of 10, Good, (13)
"The apartment, furniture, and kitchenware are clean. The apartment is spacious. I felt comfortable staying and sleeping there. "
United States
Thunyapong
The price is NZ$249
includes taxes & fees
9 Nov - 10 Nov
Serene Living Downtown STL Loft

Entire 4BR Home near Lafayette Square

The Gate
9.8 out of 10, Exceptional, (83)
"Nice spacious house close to lots of the places we planned to visit. It was well stocked vs most other places we have stayed meaning we did not have to go out and buy tp or paper towels or detergent. Also had an air fryer. Would stay here again if in STL. "
United States
chris w.
The price is NZ$503
includes taxes & fees
10 Nov - 11 Nov
Entire 4BR Home near Lafayette Square

Charming 3-bedroom house with WiFi, AC in the heart of St. Louis

2.0 star property
Northampton
8.4 out of 10, Very good, (22)
"Excellent location very clean place "
United States
kimberly b.
The price is NZ$556
includes taxes & fees
10 Nov - 11 Nov
Charming 3-bedroom house with WiFi, AC in the heart of St. Louis

Cozy Clark Suite in Frenchtown Saint Charles

St. Charles Historic District
9.6 out of 10, Exceptional, (11)
"Awesome place to stay"
United States
paul
The price is NZ$435
includes taxes & fees
8 Nov - 9 Nov
Cozy Clark Suite in Frenchtown Saint Charles

Madison House 2 -Walk to Main St

St. Charles Historic District
8.8 out of 10, Excellent, (6)
"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.
The price is NZ$445
includes taxes & fees
12 Nov - 13 Nov
Madison House 2 -Walk to Main St

Classy Midtown 3BR, King Master

The Gate
10.0 out of 10, Exceptional, (59)
"Our stay was great. Liked the open living, dining and kitchen area. Bedrooms were comfortable."
United States
Christina P.
The price is NZ$366
includes taxes & fees
11 Nov - 12 Nov
Classy Midtown 3BR, King Master

Tamm Ave 3-BR Retreat

Dogtown
9.6 out of 10, Exceptional, (44)
"Great location for the stuff we did. We did have to finish the towels and some sheets that were left in the washer and dryer wet "
United States
Leslie M.
Tamm Ave 3-BR Retreat

1830's Luxury Brick Cottage, Cozy Fireplace, right off the Cobblestone Streets!

St. Charles Historic District
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

Downtown West
6.0 out of 10, (10)
"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
The price is NZ$321
includes taxes & fees
9 Nov - 10 Nov
Downtown STL Lovely Loft w/Pool/ Free Breakfast/Free Parking

Centrally located in the Tower Grove East neighborhood!

Tower Grove East
9.8 out of 10, Exceptional, (132)
"Great stay, comfortable furnishings, quiet street. "
United States
Tracy C.
The price is NZ$297
includes taxes & fees
10 Nov - 11 Nov
Centrally located in the Tower Grove East neighborhood!

Stunning 1890's Home - Sleeps 8!

St. Charles Historic District
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.
The price is NZ$726
includes taxes & fees
9 Nov - 10 Nov
Stunning 1890's Home - Sleeps 8!

The Hare Suite at Divine Otter

St. Charles Historic District
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!

St. Charles Historic District
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.
The price is NZ$479
includes taxes & fees
10 Nov - 11 Nov
St. Charles 1860's Gem - Sleeps 6!

5th Street #1 · Historic 5th Street House - Fully Rehabbed # 1

St. Charles Historic District
9.0 out of 10, Wonderful, (10)
"Great property!!"
United States
Nicole S.
The price is NZ$492
includes taxes & fees
12 Nov - 13 Nov
5th Street #1 · Historic 5th Street House - Fully Rehabbed # 1

At home near Lafayette Square Pet-Friendly

The Gate
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!!

The Hill
9.8 out of 10, Exceptional, (154)
"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
The price is NZ$238
includes taxes & fees
10 Nov - 11 Nov
Cozy Studio Cottage on "The Hill," walkably close to everything! The Zoo, Park!!

Honky Tonk Hideaway

St. Charles Historic District
9.2 out of 10, Wonderful, (10)
"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.
Honky Tonk Hideaway

Retro Baseball Downtown Apartment

Peabody Darst Webbe
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.
The price is NZ$360
includes taxes & fees
8 Nov - 9 Nov
Retro Baseball Downtown Apartment
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 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 Overland holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Overland holiday 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 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 Overland holiday rentals we have selected for you start as low as NZ$238 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 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 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 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 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 holiday rentals in Overland?

Yes, there are holiday rentals close to the most popular sights in Overland, or you can select a more secluded option if you're looking for a relaxing stay. Overland is known for its live music and bars. Make sure you have time to check out the churches and coffee shops during your trip.

What are some of the best holiday rentals that Overland has to offer?

The St. Charles Guest House, lovely historic home, fun for families and groups: This holiday home rental outside of Overland is located on a river, and has a fireplace, a selection of games and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Overland?

With 10 Expedia holiday rentals, you're guaranteed 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 holiday rentals like in Overland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Overland. Holiday rentals offer amenities such as kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a clean environment, a holiday rental can provide a sense of safety away from public hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great choice for family gatherings.