(covers information from several alternate timelines)
The USS Enterprise (CV-6) was an aircraft carrier that served in World War II. Its successor was the USS Enterprise (CVN-65), which was the first nuclear-powered aircraft carrier. (ENT: "Storm Front"; Star Trek IV: The Voyage Home)
The first space shuttle orbiter was the Enterprise (OV-101). Benjamin Sisko kept a desktop model of the Enterprise docked with the International Space Station. (Star Trek: The Motion Picture; DS9: "Inquisition")
Enterprise NX-01 was the first warp 5 starship to be launched. The prototype of the NX-class, it was launched in 2151 and was decommissioned in 2161. Its relatively short service life can be attributed to the formation of the Federation; its technology was far behind that of some of the founding races, rendering it immediately obsolete. It participated in early first contact missions, the Xindi incident, and several other missions during its illustrious career under Captain Jonathan Archer. (Star Trek: Enterprise)
United Federation of Planets
The USS Enterprise (NCC-1701) was a Constitution-class starship that served under five captains from 2245 to 2285, including Robert April, Christopher Pike, Will Decker, and in later years Spock. Its most famous commander was Captain James T. Kirk, whose five-year mission aboard the Enterprise became legendary.
The ship subsequently had encounters with V'ger and Khan Noonien Singh before being destroyed over Genesis.(TAS: "The Counter-Clock Incident"; Star Trek: The Original Series; Star Trek: The Animated Series; Star Trek: The Motion Picture; Star Trek II: The Wrath of Khan; Star Trek III: The Search for Spock)
The USS Enterprise (NCC-1701-A) was a refit Constitution-class vessel under the command of Captain James T. Kirk. The ship was launched in 2286 and served during the Khitomer Conference prior to its decommissioning in 2293. (Star Trek IV: The Voyage Home; Star Trek V: The Final Frontier; Star Trek VI: The Undiscovered Country)
The USS Enterprise (NCC-1701-B) was a refit Excelsior-class starship launched in 2293. The ship was under the command of Captain John Harriman and was noted for rescuing 47 El-Aurians from the Nexus. (Star Trek Generations)
The USS Enterprise (NCC-1701-C) was an Ambassador-class starship that served in the early-to-mid 24th century under the command of Captain Rachel Garrett. The ship's destruction defending a Klingon outpost against four Romulan Warbirds eventually led to closer relations between the Klingon Empire and the Federation. (TNG: "Yesterday's Enterprise")
The USS Enterprise (NCC-1701-D) was a Galaxy-class starship that served under three captains from 2363 to 2371, most famously Jean-Luc Picard, who commanded the ship for the majority of its service. The ship was also briefly captained by William T. Riker and Edward Jellico. The Enterprise-D was the Federation flagship and made first contact with over thirty species. It also participated in the Klingon Civil War and was the first starship to visit another galaxy. (Star Trek: The Next Generation; Star Trek Generations)
The USS Enterprise (NCC-1701-E) was a Sovereign-class starship launched under the command of Captain Jean-Luc Picard in 2372. The ship participated in the Battle of Sector 001, the crew's insurrection against the forced relocation of the Ba'ku, and was badly damaged in the battle against the Reman Warbird Scimitar at the Battle of the Bassen Rift. (Star Trek: First Contact; Star Trek: Insurrection; Star Trek Nemesis)
Alternate timelines and realities
In an alternate timeline created when the USS Enterprise-C accidentally traveled to the future rather than being destroyed defending a Klingon outpost, the Federation was at war with the Klingon Empire. The USS Enterprise-D was the first of the Galaxy class warships and its design was geared for combat. It was likely destroyed by the attack of two Klingon Birds of Prey. (TNG: "Yesterday's Enterprise")
In the alternate timeline in which the Sphere-Builders attempted to invade the prime reality in the 26th century, the USS Enterprise (NCC-1701-J) participated in the historic Battle of Procyon V to drive them out. (ENT: "Azati Prime")
In the timeline where an anomaly threatened to destroy life, the Enterprise-D was the personal flagship of Admiral William Riker. It was fitted with a large phaser cannon and a cloaking device. Starfleet had tried to decommission her, but as an admiral, Riker got to choose his own ship. (TNG: "All Good Things...")
In the alternate reality created by a temporal incursion by Nero in 2233, the USS Enterprise (NCC-1701) was a Constitution-class starship launched in 2258 as the Federation flagship under the command of Captain Christopher Pike. Under the acting command of Cadet James T. Kirk, the crew was successful in defending Earth from the Narada. (Star Trek)
The USS Enterprise (NCC-1701-A) was a Constitution-class starship that was under construction at Starbase Yorktown in 2263 and was launched sometime afterwards following the destruction of the previous starship Enterprise. (Star Trek Beyond)
The ISS Enterprise (NX-01) was the flagship of the Imperial Starfleet. It was commanded by Captain Maximilian Forrest and was destroyed by Tholians in 2155 during the operation to capture the USS Defiant (NCC-1764). (ENT: "In a Mirror, Darkly")
The ISS Enterprise (NCC-1701) was a Constitution-class starship under the commands of Christopher Pike and James T. Kirk. The crew of this ship was one of the first Terran starships to come into contact with people from the prime universe. (TOS: "Mirror, Mirror")
The legacy of the ships named Enterprise were honored at various places, including:
- The captain's ready room aboard Enterprise NX-01: Drawings of the frigate Enterprise, USS Enterprise (CVN-65), Enterprise (OV-101), and XCV 330. (ENT: "Regeneration", "United", "These Are the Voyages...")
- In 2259 of the alternate reality, models of the Enterprise (OV-101), USS Enterprise (XCV-330) and Enterprise (NX-01) were displayed on a desk in Alexander Marcus' office alongside other iconic air and space craft. (Star Trek Into Darkness)
- The recreation room aboard the refit USS Enterprise NCC-1701: Drawings of the brig USS Enterprise, USS Enterprise (CV-6), OV-101, XCV 330, and the pre-refit NCC-1701. (Star Trek: The Motion Picture; The Making of Star Trek: The Motion Picture)
- The observation lounge aboard the USS Enterprise NCC-1701-D: Models of CVN-65, NCC-1701, USS Enterprise NCC-1701-A, USS Enterprise NCC-1701-B, and USS Enterprise NCC-1701-C. (TNG: "Encounter at Farpoint")
- The observation lounge aboard the USS Enterprise NCC-1701-E: Models of NCC-1701, NCC-1701-A, NCC-1701-B, NCC-1701-C, NCC-1701-D, and NCC-1701-E. The captain's ready room also contained a model of the NCC-1701-E. (Star Trek: First Contact; Star Trek Nemesis)
Key ships in real-world history include:
L'Entreprise (unknown – 1707) 320-ton, 24-gun, sixth-rate frigate – The first known Human ship named Enterprise. She was captured by the British and renamed HMS Enterprize in 1705.
As of 2019, the United States Navy has had eight vessels named Enterprise, of which six were commissioned and used the prefix USS (United States Ship). A ninth ship bearing the name is currently under construction.
Continental Navy of the United States
- USS Enterprise (1775 – 1777) 70-ton sloop – served on Lake Champlain. (US Navy file)
- Enterprise (1776 – 1777) 25-ton schooner – served in Chesapeake Bay. (US Navy file)
US Navy (sail) One of these ships was the inspiration for the holographic sailing ship in Star Trek Generations:
- USS Enterprise (1799 – 1823) 135-ton schooner – defeated the 14-gun Tripolitan corsair Tripoli in 1801. An 1800 refit upgraded her tonnage to 165, and in 1812 she was rerigged as a brig. (US Navy file)
- USS Enterprise (1831 – 1844) 194-ton schooner. (US Navy file)
Union Army Balloon Corps
- Enterprise (1861 – 1862) small hydrogen-gas balloon – the first balloon in US military service.
US Navy (powered)
- USS Enterprise (1877 – 1909) 1375-ton barque-rigged screw sloop-of-war. She was the first Enterprise known to use the USS prefix while in actual service. (US Navy file and pictures)
- Enterprise SP-790 (1917 – 1919) motorboat – non-commissioned, served in the 2nd Naval District during World War I. (US Navy file)
- USS Enterprise CV-6 (1938 – 1947) 19,800-ton Yorktown-class aircraft carrier – the most-decorated World War II ship in US service. (US Navy file and pictures)
- USS Enterprise CVN-65 (1961 – 2012) 85,600-ton Enterprise-class aircraft carrier – the first nuclear powered carrier, and the second such powered surface ship. (US Navy files A, B, C, D, E, and F) The CVN-65 Enterprise was decommissioned in 2013. CVN-65 was also notably played by the USS Ranger CV-61 in Star Trek IV: The Voyage Home (1986).
- Originally, the USS Gerald R. Ford (CVN-78) was planned to be named Enterprise or America before being designated to honor the late President. The Navy later announced that the Gerald R. Ford-class aircraft carrier CVN-80 would be named Enterprise.  Construction began on the USS Enterprise in August 2017; it is scheduled to be delivered and commissioned in 2025. 
- Airship Enterprise (launched 1933) First production nonrigid airship to bear the name Enterprise, served in an advertising capacity on the east coast of the United States until WWII. Airship registration: N-1A. A second Airship Enterprise served the Goodyear Tire and Rubber Company in the 1980s.
- VSS Enterprise (2014) Virgin Space Ship, the first of the Virgin Galactic fleet. While the US ships above fit the Star Trek timeline, this ship did not. It is in fact named after the Star Trek Enterprise, and space ships in Trek's history were much more advanced by this time. It crashed on 31 October 2014. 
In the William Shatner novel The Return, shortly after the destruction the of USS Enterprise-D, the Defiant-class USS Monitor (β) was temporarily placed under the joint command of Ambassador Spock, Captain Kirk, and Captain Picard to attack the Borg central node, the equipment responsible for linking the Borg Collective in its group mind. The ship was temporarily renamed USS Enterprise by her regular captain John Lewinski (β) for the duration of the mission, who noted that it was the least he could do for her new commanders.
Issue #2 of the comic mini-series Star Trek: Countdown to Darkness, set in the alternate reality right before Star Trek Into Darkness, reveals a previous USS Enterprise (β) under the command of that reality's version of Robert April (β) was in service for roughly twenty years before being decommissioned a year before the launch of the new one.
In the alternate timeline from the DS9 book trilogy Millennium, following the destruction of the USS Enterprise-E, Starfleet launched the Enterprise-class (β) USS Enterprise-F (β), which Thomas Riker described as being like the USS Defiant to the tenth power. The ship was originally commanded by Jean-Luc Picard, but was given over to William T. Riker after Picard's promotion to admiral. Among Riker's crew were Geordi La Forge, Deanna Troi, Tom Paris, and B'Elanna Torres. The Enterprise-F was lost with all hands in a horrific battle that saw the destruction of Earth. This timeline was aborted thanks to the efforts of Benjamin Sisko and the rest of Deep Space 9's crew.
The anthology Star Trek: Enterprise Logs tells the stories of various ships, both space and sea, named Enterprise.