Yes, there are.
The Boeing B-17 FLying Fortress is one example of an aircraft designed with a retractable tailwheel.
Source: USAAF via Wikimedia , Public Domain (USGOV-PD)
Another example would be the Vought F4U Corsair : Source:
Wikimedia , cc-by-sa-2.0 Doubtless
there are also other examples of aircraft similarly equipped with retractable tailwheels.
aviation.stackexchange.com/users/12720/J Walters
Concorde!
Actually a "bumper"
.Obviously it was there to protect against over-rotation on takeoff, but the relevant item on the checklist was four greens, not three.
aviation.stackexchange.com/users/18164/Plucky Underdog
As others have mentioned, yes.
Later in World War 2, speed and range became more important than weight and mechanical complexity; an extended tail wheel may be mechanically simpler to build, but adds quite a large amount of drag, affecting range and speed.
There are too many examples to list with links/
photos of them all, but a short list of examples include: Mitsubishi Zero.
P-51 Mustang.
P-40 Thunderbolt.
Later marks of the Supermarine Spitfire (around the MkVIII
from memory; I spent 6 years working on a MkV restoration).
Some models of Messerschmitt BF.109.
The F models were 'cleaned up' aerodynamically with retracting tail wheels, while the subsequent G models had a fixed wheel due to a bigger tyre for better ground handling, which didn't retract as on the F models.
Later G and K models again used a retracting wheel to lessen the drag.
Notable for being an oddball in that it's a jet tail dragger and also equipped for aircraft carrier landings would be the Supermarine Attacker .
There's an in-flight photo with the wheels up here .
aviation.stackexchange.com/users/24443/nathan
In addition to the military fighters listed above numerous civilian airplanes with conventional landing gear had retractable tailwheel, including the Beech Staggerwing, the Boeing 307, the Curtis C-46 and many others.
aviation.stackexchange.com/users/15637/Carlo Felicione
the friedrich models, earlier gustav models of the 109 and kurfurst had retractable gear
aviation.stackexchange.com/users/38921/Crazy
The Bf-109E-4's did not have retractable tailwheel, but the Friedrich which came after the E did have retractable tailwheel.
The G had a larger tailwheel to improve the on ground handling that was difficult because of the narrow track undercarriage.
This made the tailwheel unretractable.
The P-51s, many variants of spitfires, Fw-190, many P-47s, the P-36s, (which were not in service with the US but were with the French), most Yakolev fighters as mentioned above, the F4U, the Zero, the Ki-84 and many others.
The Stuka had no retractable landing gear but part of the reason was that the huge landing gear was used to reduce the airspeed in a dive.
In conclusion, most fighters and many aircraft of WWII had retractable tailwheels.
aviation.stackexchange.com/users/47514/J Lopez
A few more examples are the Soviet Tu-2 front line bomber (fully retractable) and the Il-10 attacker (partially retractable, i.e.: it folded into the fuselage but did not have a fairing).
Tu-2, note the tailwheel bay doors: Il-10, note the folded tailwheel:
aviation.stackexchange.com/users/23223/AEhere supports Monica
This comes from a slightly related question about  drag from landing gear .  A tail-dragger is the old-school layout of aircraft, particularly WW2-era fighters. It's also known as  Conventional Landing Gear .  The first two landing gear is usually retractable, but the tail wheel is not.  At least, I have never seen such a configuration with a retractable tail wheel. Has there ever been one?  Note: question excludes now more common tri-cycles.
Has there ever been a tail-dragger with retractable tail-gear?
aviation.stackexchange.com
<aircraft-design><landing-gear><drag><tail-dragger>
aviation.stackexchange.com/questions/33282
aviation.stackexchange.com/users/3674/DrZ214
There are a number of examples of a tail dragger with a retractable tail gear. One of these was Concorde. Many WWII planes had this feature as do many other fighter planes. Moreover many civilian planes had this feature in the past. Yes, there exist many models with retractable tail-gear: the Boeing B-17 FLying Fortress, the Concorde, the Beech Staggerwing, the Boeing 307, the Curtis C-46,  the friedrich models, earlier gustav models of the 109 and kurfurst, the P-51s, many variants of spitfires, Fw-190, many P-47s, the P-36s, most Yakolev fighters, the F4U, the Zero, the Ki-84, the Soviet  Tu-2  front line bomber, the  Il-10  attacker (partially retractable) and many more.
Yes, there exist many models with retractable tail-gear: the Boeing B-17 FLying Fortress, the Concorde, the Beech Staggerwing, the Boeing 307, the Curtis C-46,  the friedrich models, earlier gustav models of the 109 and kurfurst, the P-51s, many variants of spitfires, Fw-190, many P-47s, the P-36s, most Yakolev fighters, the F4U, the Zero, the Ki-84, the Soviet  Tu-2  front line bomber, the  Il-10  attacker (partially retractable) and many more.