Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a party other than the Registrant ☐ Check the appropriate box: ☒ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☐ Definitive Proxy Statement ☐ Definitive Additional Materials ☐ Soliciting Material Under §240.14a-12 Hilton Grand Vacations Inc. (Name of Registrant as Specified In Its Charter) (Name of Person(s) Filing Proxy Statement, if other than the Registrant) Payment of Filing Fee (Check the appropriate box): ☐ No fee required. ☒ Fee computed on table below per Exchange Act Rules 14a-6(i)(1) and 0-11. (1) Title of each class of securities to which the transaction applies: Common stock, par value $0.01 per share (2) Aggregate number of securities to which the transaction applies: 34,390,588 shares of common stock (3) Per unit price or other underlying value of the transaction computed pursuant to Exchange Act Rule 0-11 (set forth the amount on which the filing fee is calculated and state how it was determined): $38.02* (4) Proposed maximum aggregate value of the transaction: $1,307,358,202.82 (5) Total fee paid: $142,632.78** * Per share price based on the average of the high and low prices of Hilton Grand Vacations Inc. common stock as reported on the New York Stock Exchange on April 13, 2021. ** The fee has been calculated at a rate equal to $109.10 per $1,000,000 of the proposed maximum aggregate value of the transaction. ☐ Fee paid previously with preliminary materials. ☐ Check box if any part of the fee is offset as provided by Exchange Act Rule 0-11(a)(2) and identify the filing for which the offsetting fee was paid previously. Identify the previous filing by registration statement number, or the Form or Schedule and the date of its filing. (1) Amount previously paid: (2) Form, Schedule or Registration Statement No.: (3) Filing party: (4) Date Filed: Table of Contents PRELIMINARY PROXY STATEMENT – SUBJECT TO COMPLETION PROPOSED BUSINESS COMBINATION—YOUR VOTE IS VERY IMPORTANT Hilton Grand Vacations Inc. (“HGV”) and Dakota Holdings, Inc. (“Diamond”), which indirectly owns all of the interests in Diamond Resorts International, Inc., have entered into an Agreement and Plan of Merger, dated as of March 10, 2021 (the “merger agreement”), providing for the acquisition of Diamond by HGV through a series of transactions (the “merger”). After the completion of the merger, Diamond will cease to exist as an entity and all of its assets and liabilities will be held by Hilton Grand Vacations Borrower LLC, a wholly-owned subsidiary of HGV (“Merger Sub” or “HGV Borrower”). If the merger is completed, HGV currently anticipates issuing approximately 34,390,588 shares of its common stock (“HGV common stock”) to current Diamond stockholders (based on calculations as of April 9, 2021), subject to certain adjustments as a result of changes in certain liabilities and other items between signing and closing. As a result, based on Diamond’s current capitalization, HGV currently anticipates issuing approximately 0.32066 shares of HGV common stock (based on calculations as of April 9, 2021), plus cash in lieu of any fractional shares, without interest, for each share of Diamond Class A common stock that Diamond stockholders own other than Appraisal Shares (as defined in the merger agreement), treasury shares, and shares owned directly or indirectly by Diamond. This exchange ratio will not be adjusted to reflect stock price changes before the completion of the merger, but is subject to certain adjustments as a result of changes in certain liabilities and other items between signing and closing. Based on the closing price of HGV common stock of $40.57 on March 9, 2021, the last trading day before public announcement of the merger agreement, this estimated merger consideration represented an implied value of $ • per share of Diamond Class A common stock. Based on the closing price of HGV common stock of $ • on • , 2021, the latest practicable date before the printing of this proxy statement, this estimated merger consideration represented an implied value of $ • per share of Diamond Class A common stock. The value of the merger consideration will fluctuate with the market price of HGV common stock, which is currently traded on the New York Stock Exchange (the “NYSE”) under the symbol “HGV.” The obligations of HGV and Diamond to complete the merger are subject to the satisfaction or waiver of a number of conditions set forth in the merger agreement, a copy of which is included as Annex A to this proxy statement, including stockholder approval of the issuance of our common stock in connection with the proposed merger. HGV will hold a special meeting of its stockholders in connection with the issuance of HGV common stock in the proposed merger. Your vote is very important. Please submit a proxy to vote your shares as promptly as possible so that your shares may be represented and voted at the special meeting. The HGV board of directors unanimously recommends that HGV stockholders vote “FOR” each of the proposals being submitted to a vote of HGV stockholders at the special meeting. This proxy statement contains detailed information about HGV, the special meeting, the merger agreement and the merger. You should read this proxy statement carefully and in its entirety before voting, including the section entitled “Risk Factors” beginning on page 22 of this proxy statement. We look forward to HGV’s successful acquisition of Diamond. Sincerely, Mark D. Wang Chief Executive Officer Hilton Grand Vacations Inc. This proxy statement is dated • , 2021 and is first being mailed to HGV stockholders on or about • , 2021. Table of Contents • , 2021 NOTICE OF SPECIAL MEETING OF STOCKHOLDERS Dear Fellow Stockholder: We are pleased to invite you to attend the special meeting of stockholders (the “special meeting”) of Hilton Grand Vacations Inc. (“HGV”), a Delaware corporation, which will be held at • , on • , 2021 at • a.m., Eastern time, for the following purposes: • to consider and vote on the proposal to issue shares of HGV common stock to Diamond stockholders (the “stock issuance proposal”) under the Agreement and Plan of Merger, dated as of March 10, 2021, by and among HGV, Hilton Grand Vacations Borrower LLC, a Delaware limited liability company and a wholly-owned subsidiary of HGV (“Merger Sub” or “HGV Borrower”), Dakota Holdings, Inc., a Delaware corporation (“Diamond”) that is controlled by investment funds and vehicles managed by affiliates of Apollo Global Management, Inc. (together with its subsidiaries, “Apollo”), and the stockholders of Diamond, a copy of which is included as Annex A to the proxy statement of which this notice is a part (the “merger agreement”); • to vote upon the proposal to approve, on an advisory (non-binding) basis, the merger-related named executive officer compensation that will or may be paid to HGV’s named executive officers in connection with the merger (the “compensation proposal”); and • to vote upon the proposal to adjourn the special meeting, if necessary or appropriate, to solicit additional proxies if there are not sufficient votes to approve the stock issuance proposal (the “adjournment proposal” and together with the stock issuance proposal and compensation proposal, the “proposals”). HGV will transact no other business at the special meeting except such business as may properly be brought before the special meeting or any adjournments or postponements thereof. Please refer to the proxy statement of which this notice is a part for further information on the business to be transacted at the special meeting. HGV’s board of directors has unanimously approved the merger agreement and the acquisition of Diamond by HGV through a series of transactions as provided in the merger agreement (the “merger”) and determined that the merger agreement and the transactions contemplated thereby, and the issuance of shares of HGV common stock to Diamond stockholders under the merger agreement, are advisable and in the best interests of HGV and its stockholders. HGV’s board of directors unanimously recommends that HGV stockholders vote “FOR” each of the proposals being submitted to a vote of stockholders at the special meeting. HGV’s board of directors has fixed the close of business on • , 2021 as the record date (the “record date”) for determining HGV stockholders entitled to receive notice of, and to vote at, the special meeting or any adjournments or postponements thereof. Only holders of record of HGV common stock at the close of business on the record date are entitled to receive notice of, and to vote at, the special meeting. The presence of the holders of a majority in voting power of the stock issued and outstanding and entitled to vote at the special meeting, present in person or represented by proxy, is required to constitute a quorum for the transaction of business at the special meeting. To ensure that your vote is counted, please provide your voting instructions as soon as possible, even if you plan to attend the special meeting in person. We encourage you to vote via the internet or by telephone. You also have the option of voting by completing, signing, dating and returning the proxy card that accompanied the printed materials. Submitting your vote via the internet or by telephone or proxy card will not affect your right to vote in person if you decide to attend the special meeting. Table of Contents The approval of the stock issuance proposal and the compensation proposal requires the affirmative vote of the holders of a majority of the votes cast.