diff --git a/apps/web/components/booking/BookingListItem.tsx b/apps/web/components/booking/BookingListItem.tsx
index 695f43f1995d20..6dd0054d988d9f 100644
--- a/apps/web/components/booking/BookingListItem.tsx
+++ b/apps/web/components/booking/BookingListItem.tsx
@@ -185,6 +185,12 @@ function BookingListItem(booking: BookingItemProps) {
 
   const isAttendee = !!userSeat;
 
+  // Checks if the logged in user is the host of the booking
+  const isHost =
+    booking.user?.id != null &&
+    booking.loggedInUser.userId != null &&
+    booking.loggedInUser.userId === booking.user.id;
+
   const paymentAppData = getPaymentAppData(booking.eventType);
 
   const location = booking.location as ReturnType<typeof getEventLocationValue>;
@@ -234,6 +240,7 @@ function BookingListItem(booking: BookingItemProps) {
     showPendingPayment: paymentAppData.enabled && booking.payment.length && !booking.paid,
     isAttendee,
     cardCharged,
+    isHost,
     attendeeList,
     getSeatReferenceUid,
     t,
diff --git a/apps/web/components/booking/actions/BookingActionsDropdown.tsx b/apps/web/components/booking/actions/BookingActionsDropdown.tsx
index c0892c081541a9..66dcb7882e8730 100644
--- a/apps/web/components/booking/actions/BookingActionsDropdown.tsx
+++ b/apps/web/components/booking/actions/BookingActionsDropdown.tsx
@@ -254,6 +254,7 @@ export function BookingActionsDropdown({
     showPendingPayment,
     isAttendee,
     cardCharged,
+    isHost,
     attendeeList,
     getSeatReferenceUid,
     t,
diff --git a/apps/web/components/booking/actions/bookingActions.test.ts b/apps/web/components/booking/actions/bookingActions.test.ts
index 1c8386d09194bc..24250ca97e6294 100644
--- a/apps/web/components/booking/actions/bookingActions.test.ts
+++ b/apps/web/components/booking/actions/bookingActions.test.ts
@@ -592,6 +592,38 @@ describe("Booking Actions", () => {
       expect(isActionDisabled("cancel", futureContext)).toBe(false);
     });
 
+    it("should allow hosts to cancel bookings even when cancellation is disabled", () => {
+      const context = createMockContext({
+        isHost: true,
+        isDisabledCancelling: true,
+        isBookingInPast: false,
+      });
+
+      expect(isActionDisabled("cancel", context)).toBe(false);
+    });
+
+    it("should not allow hosts to cancel already cancelled bookings", () => {
+      const context = createMockContext({
+        isHost: true,
+        isDisabledCancelling: true,
+        isBookingInPast: false,
+        isCancelled: true,
+      });
+
+      expect(isActionDisabled("cancel", context)).toBe(true);
+    });
+
+    it("should not allow hosts to cancel rejected bookings", () => {
+      const context = createMockContext({
+        isHost: true,
+        isDisabledCancelling: true,
+        isBookingInPast: false,
+        isRejected: true,
+      });
+
+      expect(isActionDisabled("cancel", context)).toBe(true);
+    });
+
     it("should disable video actions for non-past bookings", () => {
       const context = createMockContext({ isBookingInPast: false });
 
diff --git a/apps/web/components/booking/actions/bookingActions.ts b/apps/web/components/booking/actions/bookingActions.ts
index 97544f63fdbff4..8f21304da4b5d8 100644
--- a/apps/web/components/booking/actions/bookingActions.ts
+++ b/apps/web/components/booking/actions/bookingActions.ts
@@ -24,6 +24,7 @@ export interface BookingActionContext {
   showPendingPayment: boolean;
   isAttendee: boolean;
   cardCharged: boolean;
+  isHost?: boolean;
   attendeeList: Array<{
     name: string;
     email: string;
@@ -237,7 +238,7 @@ export function shouldShowIndividualReportButton(context: BookingActionContext):
 }
 
 export function isActionDisabled(actionId: string, context: BookingActionContext): boolean {
-  const { booking, isBookingInPast, isDisabledRescheduling, isDisabledCancelling, isAttendee, isCancelled, isRejected } = context;
+  const { booking, isBookingInPast, isDisabledRescheduling, isDisabledCancelling, isAttendee, isHost, isCancelled, isRejected } = context;
 
   switch (actionId) {
     case "reschedule":
@@ -263,6 +264,7 @@ export function isActionDisabled(actionId: string, context: BookingActionContext
         isWithinMinimumNotice
       );
     case "cancel":
+      if (isHost && !isBookingInPast && !isCancelled && !isRejected) return false;
       return isDisabledCancelling || isBookingInPast || isCancelled || isRejected;
     case "view_recordings":
       return !(isBookingInPast && booking.status === BookingStatus.ACCEPTED && context.isCalVideoLocation);
diff --git a/packages/features/bookings/lib/handleCancelBooking.ts b/packages/features/bookings/lib/handleCancelBooking.ts
index 92f278c543f4d0..a8227774ba84b2 100644
--- a/packages/features/bookings/lib/handleCancelBooking.ts
+++ b/packages/features/bookings/lib/handleCancelBooking.ts
@@ -208,16 +208,35 @@ async function handler(input: CancelBookingInput, dependencies?: Dependencies) {
     throw new HttpError({ statusCode: 400, message: "User not found" });
   }
 
-  if (bookingToDelete.eventType?.disableCancelling) {
+  let isCancellationUserHost = false;
+  if (userId) {
+    if (bookingToDelete.userId === userId) {
+      isCancellationUserHost = true;
+    }
+    else if (bookingToDelete.eventType?.hosts?.some((host) => host.user.id === userId)) {
+      isCancellationUserHost = true;
+    }
+    else if (bookingToDelete.eventType?.owner?.id === userId) {
+      isCancellationUserHost = true;
+    }
+    else if (
+      await PrismaOrgMembershipRepository.isLoggedInUserOrgAdminOfBookingHost(
+        userId,
+        bookingToDelete.userId
+      )
+    ) {
+      isCancellationUserHost = true;
+    }
+  }
+
+  // Only the host can cancel the booking even when the cancellation is disabled for the event
+  if (!isCancellationUserHost && bookingToDelete.eventType?.disableCancelling) {
     throw new HttpError({
       statusCode: 400,
       message: "This event type does not allow cancellations",
     });
   }
 
-  const isCancellationUserHost =
-    bookingToDelete.userId === userId || bookingToDelete.user.email === cancelledBy;
-
   if (
     !platformClientId &&
     !cancellationReason?.trim() &&
diff --git a/packages/features/bookings/lib/handleCancelBooking/test/handleCancelBooking.test.ts b/packages/features/bookings/lib/handleCancelBooking/test/handleCancelBooking.test.ts
index 9bbe4784126ece..7ba9564030d328 100644
--- a/packages/features/bookings/lib/handleCancelBooking/test/handleCancelBooking.test.ts
+++ b/packages/features/bookings/lib/handleCancelBooking/test/handleCancelBooking.test.ts
@@ -700,7 +700,6 @@ describe("Cancel Booking", () => {
       })
     );
 
-    // This should throw an error with current implementation
     await expect(
       handleCancelBooking({
         bookingData: {
@@ -708,6 +707,7 @@ describe("Cancel Booking", () => {
           uid: uidOfBookingToBeCancelled,
           cancelledBy: organizer.email,
         },
+        userId: organizer.id,
       })
     ).rejects.toThrow("Cancellation reason is required when you are the host");
   });