Sikeston Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Sikeston holiday rentals

A modern kitchen with stainless steel appliances, wooden cabinets, and a white countertop.

1. The Cutie Patootie on Helen- Cute, Cozy, Comfortable - 3 BR Home in Dexter, MO

The Cutie Patootie on Helen- Cute, Cozy, Comfortable - 3 BR Home in Dexter, MO
Dexter
10.0 out of 10, Exceptional, (4 reviews)
"Perfect place for our stay on the way to North Carolina! Clean, cozy and convenient!"
United States
Robert G.
The price is AU$219
includes taxes & fees
17 Nov - 18 Nov
The Cutie Patootie on Helen- Cute, Cozy, Comfortable - 3 BR Home in Dexter, MO
A living room with a TV, a fireplace, a sofa, and wall art.

2. Little Blue Cottage on Spanish

Little Blue Cottage on Spanish
Cape Girardeau
8.4 out of 10, Very good, (59 reviews)
"Great cute place. "
United States
Jeremy W.
The price is AU$146
includes taxes & fees
12 Nov - 13 Nov
Little Blue Cottage on Spanish
A two-story house with a front porch, a covered entryway, and a small garden with white flowers.

3. Dexter Victorian Homestead- Brand NEW Remodel April 2026. VERY Clean & Cozy

Dexter Victorian Homestead- Brand NEW Remodel April 2026. VERY Clean & Cozy
Dexter
8.0 out of 10, Very good, (40 reviews)
"Overall, it was a good experience. I would stay again."
United States
Tammy G.
The price is AU$302
includes taxes & fees
12 Nov - 13 Nov
Dexter Victorian Homestead- Brand NEW Remodel April 2026. VERY Clean & Cozy
A row of colorful houses with a clear sky and trees in the background.

4. Enchanted Mermaid A-Frame | Creek + Fire pit | Pet Friendly

Enchanted Mermaid A-Frame | Creek + Fire pit | Pet Friendly
Cape Girardeau
10.0 out of 10, Exceptional, (1 review)
"Very cute, especially because it's pet friendly! Currently building additional structures on site but appears almost complete and still a beautiful setting and property."
United States
Elizabeth K.
The price is AU$329
includes taxes & fees
14 Nov - 15 Nov
Enchanted Mermaid A-Frame | Creek + Fire pit | Pet Friendly
A modern living room with a wooden ceiling, a stone fireplace, a TV mounted on the wall, and a bar area with stools.

5. The Twisted Sassafras Treehouse

The Twisted Sassafras Treehouse
Cape Girardeau
10.0 out of 10, Exceptional, (41 reviews)
"The hosts were excellent."
United States
Jason L.
The price is AU$529
includes taxes & fees
7 Dec - 8 Dec
The Twisted Sassafras Treehouse
A two-story house with a front porch, a small garden, and a white picket fence.

6. 3+ acre Home: Pool Table, Putt-Putt, 4 miles to Downtown and SEMO, Summer Pool

3+ acre Home: Pool Table, Putt-Putt, 4 miles to Downtown and SEMO, Summer Pool
Cape Girardeau
8.8 out of 10, Excellent, (46 reviews)
"Will definitely book again! Great location, comfortable stay."
United States
Pynktoria !.
The price is AU$432
includes taxes & fees
24 Nov - 25 Nov
3+ acre Home: Pool Table, Putt-Putt, 4 miles to Downtown and SEMO, Summer Pool
An outdoor seating area with Adirondack chairs and a wooden pergola, surrounded by trees and string lights.

7. The Little Château | Woodland Escape

The Little Château | Woodland Escape
Cape Girardeau
The price is AU$316
includes taxes & fees
23 Nov - 24 Nov
The Little Château | Woodland Escape
A house with a backyard swimming pool, outdoor furniture, and a barbecue area.

8. 4-Bedroom Home - 2 King Beds, Summer Pool, Pool Table, Air Hockey + More

4-Bedroom Home - 2 King Beds, Summer Pool, Pool Table, Air Hockey + More
Cape Girardeau
9.8 out of 10, Exceptional, (11 reviews)
"Nice place, great times"
United States
Jace W.
The price is AU$786
includes taxes & fees
12 Nov - 13 Nov
4-Bedroom Home - 2 King Beds, Summer Pool, Pool Table, Air Hockey + More
A compact kitchen with wooden cabinets and a dining area with a table and chairs.

9. Villa B offers peace and quiet with beautiful views of the countryside.

Villa B offers peace and quiet with beautiful views of the countryside.
Jackson
9.8 out of 10, Exceptional, (16 reviews)
"We were only there for 1 night for a business trip but it was perfect for our stay. Very clean and comfortable and the host was onsite to welcome us. She even gave us a tip on the best place nearby for dinner that we will be going to any time we can in the future. I would gladly stay here again for future trips."
United States
Terry H.
The price is AU$248
includes taxes & fees
12 Nov - 13 Nov
Villa B offers peace and quiet with beautiful views of the countryside.
An outdoor seating area with Adirondack chairs and a wooden pergola, surrounded by trees and string lights.

10. Romantic Creekside Retreat | Fireplace | Deck | Pet Friendly

Romantic Creekside Retreat | Fireplace | Deck | Pet Friendly
Cape Girardeau
10.0 out of 10, Exceptional, (3 reviews)
"The house was very clean and Will kept and the whole property was well maintained. It was very comfortable and nicely decorated. The host was very responsive and helpful! Would definitely stay again and recommend."
United States
Sara C.
The price is AU$316
includes taxes & fees
21 Nov - 22 Nov
Romantic Creekside Retreat | Fireplace | Deck | Pet Friendly
Exterior

11. The Little Cape Lofted Cottage | Creek & Nature

The Little Cape Lofted Cottage | Creek & Nature
Cape Girardeau
9.0 out of 10, Wonderful, (2 reviews)
"It was very clean and had a good feel. It was well stocked. I appreciated the cute little ice tray in the freezer that was full. I also appreciated 4 waters in the fridge. The bed on the loft upstairs was atrocious. You can feel the springs through the mattress. The downstairs bed was good. The pillows were fantastic! I’m a pillow snob. We needed a quick place to land for a church function so I can’t say much about the outside amenities as we weren’t there much. But it was a beautifully tucked...
United States
Trisha S.
The price is AU$325
includes taxes & fees
12 Nov - 13 Nov
The Little Cape Lofted Cottage | Creek & Nature
A kitchen with wooden cabinets, a black refrigerator, a microwave, a stove, and a ceiling fan. There are three stools at the island.

12. Relax in the country at Countryside Villas! - Villa A

Relax in the country at Countryside Villas! - Villa A
Jackson
10.0 out of 10, Exceptional, (39 reviews)
"Great place to stay, felt like home away from home. "
United States
Brittany
The price is AU$248
includes taxes & fees
16 Nov - 17 Nov
Relax in the country at Countryside Villas! - Villa A
A log cabin interior with a stone fireplace, leather sofa, and a mounted deer head.

13. Gorgeous 1856 Log Cabin, Completely Renovated

Gorgeous 1856 Log Cabin, Completely Renovated
Jackson
10.0 out of 10, Exceptional, (6 reviews)
"incredible place. I was there for work, but it was a really nice relaxing area to retreat too, and also get some work done in a serene environment. It would be an incredible place for an entire family. And, a good place for friends to get together."
United States
Chandler G.
The price is AU$423
includes taxes & fees
12 Nov - 13 Nov
Gorgeous 1856 Log Cabin, Completely Renovated
Exterior

14. Purple Tiny House with Fire pit & Nature

Purple Tiny House with Fire pit & Nature
Cape Girardeau
10.0 out of 10, Exceptional, (1 review)
"First time staying in the purple house, second time staying at the property. 10/10 recommend"
United States
Shawn A.
The price is AU$288
includes taxes & fees
23 Nov - 24 Nov
Purple Tiny House with Fire pit & Nature
A modern kitchen with a large island, white cabinetry, and a brick accent wall.

15. Beautifully Renovated Farmhouse in Jackson, MO

Beautifully Renovated Farmhouse in Jackson, MO
Jackson
9.4 out of 10, Exceptional, (3 reviews)
" great stay,property landscape nicely manicured, quiet and relaxing inside and outside of the the dwelling."
United States
Sandy S.
The price is AU$413
includes taxes & fees
16 Nov - 17 Nov
Beautifully Renovated Farmhouse in Jackson, MO
A bedroom with a bed, a bottle of J. Roget champagne, two glasses, and a plate with snacks.

16. The Cottage, Rusted Route Farms

The Cottage, Rusted Route Farms
Jackson
10.0 out of 10, Exceptional, (3 reviews)
"This Cottage was very nice and clean and well maintained. The meat tray that we ordered and the breakfast tray was beyond Fabulous!!! My husband is still talking about it. . .Rick & Renee Christman"
United States
Renee C.
The price is AU$275
includes taxes & fees
15 Nov - 16 Nov
The Cottage, Rusted Route Farms
A kitchen with grey cabinets, a stainless steel dishwasher, a microwave, and an oven.

17. Cozy 2-bedroom house in tranquil Cape Girardeau, close to Semo & Hospitals

Cozy 2-bedroom house in tranquil Cape Girardeau, close to Semo & Hospitals
Cape Girardeau
The price is AU$280
includes taxes & fees
10 Dec - 11 Dec
Cozy 2-bedroom house in tranquil Cape Girardeau, close to Semo & Hospitals
A cozy room with a wooden table and chairs, a large window, and a door with a sign.

18. Cozy cabins on beautiful Horseshoe Lake

Cozy cabins on beautiful Horseshoe Lake
Olive Branch
9.8 out of 10, Exceptional, (44 reviews)
"Super communication! . Accommodating. Nice people"
United States
JASEN
The price is AU$194
includes taxes & fees
12 Nov - 13 Nov
Cozy cabins on beautiful Horseshoe Lake
A single-story house with a gabled roof, a front porch with two chairs, and a front door with a decorative glass panel.

19. Spacious 3-bedroom 2 story house in New Madrid near boat ramp with a toy room!

Spacious 3-bedroom 2 story house in New Madrid near boat ramp with a toy room!
New Madrid
10.0 out of 10, Exceptional, (1 review)
"The host was very quick to respond and so great to work with for on our stay. "
United States
Jessica S.
The price is AU$502
includes taxes & fees
12 Nov - 13 Nov
Spacious 3-bedroom 2 story house in New Madrid near boat ramp with a toy room!
A small, single-story building with a wooden exterior and large windows.

20. The Rested Duck Mallard Room

The Rested Duck Mallard Room
Olive Branch
9.4 out of 10, Exceptional, (32 reviews)
"This is an excellent place to stay. With a nice lake right across the street. If i. In the are i will stay again for sure"
United States
mike b.
The price is AU$194
includes taxes & fees
12 Nov - 13 Nov
The Rested Duck Mallard Room
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.
View all properties

Find holiday rentals that suit your style

cabin image
Cabins
Cabins
Apartment image
Apartments
Apartments

Find out more about Sikeston

Everything you need to know about Sikeston 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 Sikeston 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 Sikeston holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Sikeston holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Sikeston. 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Sikeston 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 Sikeston holiday rentals we have selected for you start as low as AU$145 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Sikeston rentals

At Expedia, we put the best Sikeston 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 Sikeston 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 Sikeston 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 Sikeston. 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 a holiday rental in Sikeston?

Yes, there are holiday rentals close to the most popular sights in Sikeston, or you can select a more secluded option if you're looking for a relaxing stay. Tourists like the array of shops and top-notch restaurants in Sikeston. Make sure you allow time to enjoy the riverfront during your holiday.

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

* On the Wine Trail * Hot Tub * Wi-Fi *: This holiday home rental outside of Sikeston is located on a lake, and has a patio, 1 hot tub and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

What’s there to see and do in Sikeston?

Cultural attractions include Sikeston Depot Museum, whereas Central Park is a spot to enjoy nature. In the wider area, you’ll find Front Street Studio & Art Gallery and Stoddard County Civil War Memorial Cemetery.

What’s a holiday rental in Sikeston like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Sikeston. Holiday rentals offer amenities such as WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a clean environment, a holiday rental can offer a sense of security away from public hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for family gatherings.