Pilot Knob Vacation Rentals

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Check prices for these dates

In two weeks
Jan 16 - Jan 18
In two months
Feb 27 - Mar 1
In three months
Mar 27 - Mar 29
In four months
Apr 24 - Apr 26

Our top choices for Pilot Knob vacation rentals

Property grounds
5 camper hookups on a beautiful private lake.

5 camper hookups on a beautiful private lake.

5 camper hookups on a beautiful private lake.
1.0 star property
Ironton
10.0 out of 10, Exceptional, (1)
"Great place to enjoy camping"
United States
ChangHee S.
$32 nightly
The price is $32
Dec 30 - Dec 31
Total with taxes and fees
5 camper hookups on a beautiful private lake.
Private kitchen
Cozy 1-bedroom house with AC and WiFi in charming Farmington

Cozy 1-bedroom house with AC and WiFi in charming Farmington

Cozy 1-bedroom house with AC and WiFi in charming Farmington
Farmington
10.0 out of 10, Exceptional, (6)
"A very nice place to stay. It is close to everything we were interested in doing.Everything worked as advertised. "
United States
Cary B.
$179 nightly
The price is $185
Dec 30 - Dec 31
Total with taxes and fees
Cozy 1-bedroom house with AC and WiFi in charming Farmington
Exterior
Lake Road Cabin C — Million Dollar Ozark View!

Lake Road Cabin C — Million Dollar Ozark View!

Lake Road Cabin C — Million Dollar Ozark View!
Ironton
10.0 out of 10, Exceptional, (24)
"Girls weekend enjoyed our time. Just a great little cabin so we could enjoy the parks!"
United States
Jeanine H.
$149 nightly
The price is $158
Dec 30 - Dec 31
Total with taxes and fees
Lake Road Cabin C — Million Dollar Ozark View!
Smart TV
In-law Suite

In-law Suite

In-law Suite
Leadwood
9.8 out of 10, Exceptional, (14)
"Well taken care of, nice amenities, comfortable."
United States
Daniel K.
$198 nightly
The price is $198
Dec 30 - Dec 31
Total with taxes and fees
In-law Suite
Fridge, microwave, oven, stovetop
Charming 1-bd house in Downtown Farmington, 1block from Police & Fire stations

Charming 1-bd house in Downtown Farmington, 1block from Police & Fire stations

Charming 1-bd house in Downtown Farmington, 1block from Police & Fire stations
Farmington
8.6 out of 10, Excellent, (4)
"Great place. "
United States
Diana
Charming 1-bd house in Downtown Farmington, 1block from Police & Fire stations
Exterior
Couples Retreat with hot tub (cabin2)

Couples Retreat with hot tub (cabin2)

Couples Retreat with hot tub (cabin2)
Leadwood
9.6 out of 10, Exceptional, (21)
"Nive quite lil getawaynyet close to what you needed "
United States
Do more a.
$147 nightly
The price is $158
Jan 14 - Jan 15, 2026
Total with taxes and fees
Couples Retreat with hot tub (cabin2)
Living area
Modern Newly built 2-bedroom house minutes from downtown Park Hills

Modern Newly built 2-bedroom house minutes from downtown Park Hills

Modern Newly built 2-bedroom house minutes from downtown Park Hills
Park Hills
8.6 out of 10, Excellent, (7)
"Stayed here as it was close to our newly purchased home. The home was comfortable and quiet. "
United States
Greg S.
$210 nightly
The price is $210
Jan 3 - Jan 4, 2026
Total with taxes and fees
Modern Newly built 2-bedroom house minutes from downtown Park Hills
Outdoor dining
Cabin 1 at the Pallet Factory

Cabin 1 at the Pallet Factory

Cabin 1 at the Pallet Factory
Leadwood
9.6 out of 10, Exceptional, (39)
"Just what we expected. Very quiet and secluded. Close to towns. "
United States
Cheyenne F.
$145 nightly
The price is $156
Jan 6 - Jan 7, 2026
Total with taxes and fees
Cabin 1 at the Pallet Factory
Fridge, microwave, oven, stovetop
Cozy Three bedroom home in Central Farmington

Cozy Three bedroom home in Central Farmington

Cozy Three bedroom home in Central Farmington
Farmington
9.6 out of 10, Exceptional, (29)
"House was adorable and comfortable. Location close to everything. Drive to The Landing was not bad at all. Host was friendly and available. I would stay again!"
United States
Jody C.
$237 nightly
The price is $247
Dec 30 - Dec 31
Total with taxes and fees
Cozy Three bedroom home in Central Farmington
Property grounds
Hillside Cabin #2 Annapolis, MO Black River

Hillside Cabin #2 Annapolis, MO Black River

Hillside Cabin #2 Annapolis, MO Black River
Annapolis
9.4 out of 10, Exceptional, (59)
"great place to get away. plan to cook/grill there, or drive 30 minutes for food. however, this solitude and quiet is exactly why we booked here. and gorgeous roads, hikes, sites in every direction."
United States
Hans S.
$220 nightly
The price is $220
Dec 30 - Dec 31
Total with taxes and fees
Hillside Cabin #2 Annapolis, MO Black River
Outdoor dining
"The Hideaway 2" Charming 2-bedroom house in delightful Farmington with WiFi, AC

"The Hideaway 2" Charming 2-bedroom house in delightful Farmington with WiFi, AC

"The Hideaway 2" Charming 2-bedroom house in delightful Farmington with WiFi, AC
2.0 star property
Farmington
10.0 out of 10, Exceptional, (8)
"It is a very nice place and very comfortable has everything you could possibly need for homeaway from home."
United States
Scott
$222 nightly
The price is $233
Jan 4 - Jan 5, 2026
Total with taxes and fees
"The Hideaway 2" Charming 2-bedroom house in delightful Farmington with WiFi, AC
Private kitchen
Parkside B&B

Parkside B&B

Parkside B&B
Farmington
10.0 out of 10, Exceptional, (1)
"Great property, quiet, clean, home away from home. Thank you"
United States
ana G.
$234 nightly
The price is $234
Jan 7 - Jan 8, 2026
Total with taxes and fees
Parkside B&B
Fridge, microwave, oven, stovetop
Hillside Cabin #5 Annapolis, MO

Hillside Cabin #5 Annapolis, MO

Hillside Cabin #5 Annapolis, MO
Annapolis
9.2 out of 10, Wonderful, (5)
"Great location and very clean."
United States
Mary C.
$220 nightly
The price is $220
Dec 30 - Dec 31
Total with taxes and fees
Hillside Cabin #5 Annapolis, MO
Outdoor dining
"The Hideaway 1" Charming 2-bedroom house with WiFi, AC in fabulous Farmington

"The Hideaway 1" Charming 2-bedroom house with WiFi, AC in fabulous Farmington

"The Hideaway 1" Charming 2-bedroom house with WiFi, AC in fabulous Farmington
2.0 star property
Farmington
10.0 out of 10, Exceptional, (13)
"Great place and very comfortable! Hosts were super attentive when our door code didn’t work and got us sorted out right away. "
United States
Kyser B.
$224 nightly
The price is $235
Dec 30 - Dec 31
Total with taxes and fees
"The Hideaway 1" Charming 2-bedroom house with WiFi, AC in fabulous Farmington
Fridge, microwave, oven, stovetop
The Shack- 3 bedroom finished house

The Shack- 3 bedroom finished house

The Shack- 3 bedroom finished house
Leadwood
8.6 out of 10, Excellent, (9)
"Was pretty clean and overall enjoyed our stay"
United States
Nicole V.
$197 nightly
The price is $197
Jan 14 - Jan 15, 2026
Total with taxes and fees
The Shack- 3 bedroom finished house
Outdoor dining
Hillside Cabin #1 Annapolis, MO Black River

Hillside Cabin #1 Annapolis, MO Black River

Hillside Cabin #1 Annapolis, MO Black River
Annapolis
9.4 out of 10, Exceptional, (36)
"The cabin was exactly like the pictures showed. It worked out perfectly for our family with just enough room to spread out, and with a large main area that we could hang out together comfortably. We took advantage of the spacious patio and enjoyed a fire each night. I would definitely stay again."
United States
Amy A.
$255 nightly
The price is $255
Dec 30 - Dec 31
Total with taxes and fees
Hillside Cabin #1 Annapolis, MO Black River
Fridge, microwave, oven, stovetop
FS Rental #4 Annapolis, MO Black River

FS Rental #4 Annapolis, MO Black River

FS Rental #4 Annapolis, MO Black River
Annapolis
9.6 out of 10, Exceptional, (7)
"Loved the cabin and the outdoor seating area. Definitely recommend for anyone traveling in the area. "
United States
Corey M.
$211 nightly
The price is $211
Jan 1 - Jan 2, 2026
Total with taxes and fees
FS Rental #4 Annapolis, MO Black River
Fridge, microwave, oven, stovetop
Small Town Lodge - Annapolis, MO Black River

Small Town Lodge - Annapolis, MO Black River

Small Town Lodge - Annapolis, MO Black River
Annapolis
9.0 out of 10, Wonderful, (7)
"Owner communicated well and the place was a nice clean place for us to stay "
United States
Jeremy H.
$254 nightly
The price is $254
Dec 30 - Dec 31
Total with taxes and fees
Small Town Lodge - Annapolis, MO Black River
Property grounds
Newly remodeled house minutes away from downtown, golf courses + BIG back yard

Newly remodeled house minutes away from downtown, golf courses + BIG back yard

Newly remodeled house minutes away from downtown, golf courses + BIG back yard
2.0 star property
Farmington
10.0 out of 10, Exceptional, (22)
"very nice house and good location . had so many things to enjoy"
United States
Peter V.
$198 nightly
The price is $209
Jan 6 - Jan 7, 2026
Total with taxes and fees
Newly remodeled house minutes away from downtown, golf courses + BIG back yard
Exterior
The Sutton House 2 blocks from Main Street & Courthouse Square

The Sutton House 2 blocks from Main Street & Courthouse Square

The Sutton House 2 blocks from Main Street & Courthouse Square
Ironton
10.0 out of 10, Exceptional, (45)
"Adorable house with everyone you need provided! Super clean and the beds were very comfy. Will stay here again on our next trip to the area. "
United States
Brandi
$142 nightly
The price is $160
Jan 11 - Jan 12, 2026
Total with taxes and fees
The Sutton House 2 blocks from Main Street & Courthouse Square
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 Pilot Knob Hotel Reviews

Newly remodeled house minutes away from downtown, golf courses + BIG back yard

Newly remodeled house minutes away from downtown, golf courses + BIG back yard

10/10 Excellent
"Tidy and cozy home near the center of Farmington. Great property for a small group or family b"
Brent S. 1-night trip
Posted 1 day ago
Newly remodeled house minutes away from downtown, golf courses + BIG back yard

Find out more about Pilot Knob

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

Pilot Knob vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pilot Knob. 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 Pilot Knob 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 $139 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 Pilot Knob rentals

At Expedia, we put the best Pilot Knob 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 Pilot Knob 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 Pilot Knob 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 Pilot Knob. 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 a vacation rental in Pilot Knob?

Yes, we offer vacation rentals close to well known sights in Pilot Knob, or you can choose a secluded option if you're looking for relaxation. Pilot Knob is known for its restaurants.

What's the top vacation rental in Pilot Knob?

Newly remodeled house minutes away from downtown, golf courses + BIG back yard: You might want to consider this vacation rental near Pilot Knob, which offers a fireplace, a selection of games, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

What can I see and do in Pilot Knob?

While you're exploring the area, Big River and Shepherd Mountain Bike Park and Hiking Trails are a couple of picturesque spots to get outside and enjoy nature. Elephant Rocks State Park and Taum Sauk Mountain State Park are a couple of places you'll find in the larger area.

What are vacation rentals like in Pilot Knob?

Vacation rentals are privately owned properties you can reserve for several days or longer in Pilot Knob. Vacation rentals feature extras like laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a clean environment, vacation rentals can offer a sense of seclusion away from public hotel elevators and busy concierge desks while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular option for families.